Forever Alone: These Dating Fails Are Utterly Excruciating

June 18, 2023 | Mathew Burke

Forever Alone: These Dating Fails Are Utterly Excruciating

Ah, romance. To some people out there, it seems to come as second nature. To the rest of us, though, it's more like a battlefield. A battlefield strewn with embarrassing memories and dashed dreams. But hey, at least the unlucky in love aren't alone. These warriors shared their dating fails online and they're equal parts excruciating and hilarious.

1. Bad Sense Of Humor

I had a big crush on this one girl from my school, and she was definitely aware of my feelings. She seems to have felt the same way about me, as she decided one day she was going to do something to try and impress me. What did she decide to do to try and impress me, you ask? She went up to a smaller kid and started making fun of them right in front of me, then looked over at me for approval.

What she didn’t realize was that this smaller kid she had picked out for ridicule was actually my little sister. I guess she didn’t know that we were related because we have two different last names. What she did would have been bad enough if she had been making fun of any kid, but there was definitely no way I could ever view her the same again after witnessing this particular incident go down.

date fails

2. Takes One To Know One

I commented that I was glad we finally went on a date. We'd been circling each other for so long that I kinda KNEW something would have to happen eventually. Of course, I didn't say that, I just said: "Well, it's really nice to finally be out on a date with you!" That’s when she said the absolute worst thing. She went quiet and then asked, "...this was a date?"

Dark Secrets factsShutterstock

3. A Blast From The Past

About two years ago, I divorced my wife after she cheated with a guy she met at my mother's funeral. Six months after the divorce, I'm on my first date with a girl named Heidi. She wanted to stop by a local tavern that was hosting a charity benefit. We did…Worst decision ever. I walk in the front door and immediately I am face to face with the guy who screwed my wife.

He and I grew up as friends but lost touch until he came to mom's funeral. He attempted to say something to me, and I immediately cut him off and threatened him rather harshly. He left. I spent the next 30 minutes explaining what just happened to her. She said I should have punched him...

Worst Thing Done on a Date FactsShutterstock

4. It Runs In The Family

Was at a friend's brother's 21st birthday party and was standing around talking with some other guys. On the driveway, a bunch of girls were dancing to the music. It was a really chill night. But it was about to get a lot chillier. The guy next to me said to the guy on his other side "How about the rack on that blonde chick?" The other guy replied, "That's my daughter".

Speak to the Manager factsShutterstock

5. Is That With Two M’s?

I forgot a girl’s name the night I met her. But I was talking to her for hours, we made out. It was great. Then I went to get her number and had forgotten her, trying to play it cool as she handed the phone back, I was like "Oh how do I spell your name sorry?" She replied, "Uh.,. it’s S...A…M?" Facepalm.

Adam Levine quizShutterstock

6. Funeral Jams

I had a Hitch-style moment once. I met a girl at a party. We both loved music, and she mentioned her favorite band was also my favorite band at the time (Brand New, if you are curious). We make plans for her to come to my apartment and then go to dinner. When she gets to my place, I strategically have some Brand New playing in the background.

She hears the song and immediately begins hysterically sobbing. I'm freaking out, and then she reveals what's going on. It turns out her grandpa had passed of cancer 3 months prior and the song (Guernica) was something she listened to multiple times a day to cope with his passing. Well, there was no coming back from that. We didn't make it to dinner.

Toxic Partners factsShutterstock

7. Keeping It On This Side Of The Family

There was a couple at my work having drinks. Girl went to the toilet, came back, and admitted that she’d been sleeping with the guy’s brother. Apparently, glasses were thrown across the room and they both got kicked out.

Cringeworthy Dates factsMax Pixel

8. Hiding In Plain Sight

In what I thought at the time was a pretty romantic gesture, I gave my long-time high school crush a walkie-talkie on Valentine’s Day because she had to babysit that evening at a house near mine. This was before the days of cellular phones. I hid in the bushes and talked to her on the walkie-talkie almost all night.

Towards the end of the night, some neighbors didn't take kindly to seeing some sketchy teenager skulking around the neighborhood with a walkie-talkie. It wasn’t long before someone called the authorities on me. I lived in a small but affluent town; so whenever the officers were involved in something, more than enough units showed up to respond.

So I'm sitting in a bush talking to my crush about Pearl Jam or something really stupid, when all of a sudden five cop cars come speeding down the block, slam on their brakes in front of my hedge, and light me up with the spotlight. They order me over their loudspeaker to come out with my hands up right away.

Note that this was a quiet suburban neighborhood at the crack of 11:30 in the evening, so everyone in the area quickly realized that something was up and started turning their collective attention towards me. I ditched the walkie-talkie into the bush because I didn't want to take my crush down with me and shimmied out of the hedge.

I'm now standing with a bunch of officers at the front of one of the cars. The flashing lights are still on. More and more neighbors are coming out to watch, as well as peeking through their blinds, but somehow I remain calm, cool, and collected. After all, this was all in the name of love, right? It couldn’t possibly turn out badly for me! I was so, so wrong.

I explained to the officers that this was merely a romantic gesture for my "girlfriend" gone totally wrong. For some reason, I thought that if I told the officers she was my girlfriend, they'd go easier on me. So, they have me fetch the walkie-talkie from the bushes and I give it to the main cop. He was such a jerk!

He immediately picks up the walkie-talkie and says into it, "Hey there, is (insert my name here) your boyfriend?" to which she responds, "Ummmm, definitely not.".. That was when I realized that the gesture had backfired. Honestly, there was a lot more to my exchange with the officers after that. But to make a long story short, they just let me go in the end so that I could lick my pitiful teenage rejection wounds.

The girl and I continued to stay friends after that. I still retained my crush on her, but I knew where we stood and didn’t try any further stunts of this nature. From that night on, the neighbors probably all thought I was some kind of a weirdo and never looked at me the same again. I would imagine that they all cheered on the day I left for college.

Romantic Backfired FactsPublic Domain Pictures

9. Playing The Wrong Tune

Brought my date to my friend's house. Friend pressures me into playing guitar. I played "Needle and the Damage Done"; first thing that came to mind. Why? Dunno. Turns out her brother had passed of an OD not long before. Yeah, that date became very awkward and chilly after my little serenade...

Young couple relaxing playing guitar on living room sofa.

10. Learning About Her Diary

Let me sum it up for you: I was already trying to escape by the time she told me about her poop diary.

Students This Dumb FactsPxHere

11. Left Behind My Own Mountains…

Went on a 4-day date/hike through the wilds of Alaska. It was a trip over Raven Glacier, and the surrounding areas. Before we started the hike, we felt a nice breakfast would be a smart thing to do, so we stop at a local diner to partake of the local cuisine. What's this on the menu? Reindeer sausage? Sounds wonderful!

I've never had reindeer before and the little pepper next to the name showed it was spicy, and man I love me some heat! If your food does not bite you back, it ain't worth eatin', I always say. So, I eat not one but TWO giant spicy reindeer sausages right before going on a multi-day hike over mountains and glaciers. What the holy heck was I thinking!

After about four hours of climbing up switchbacks. the low rumbling down deep in my guts began. It got BAD. I mean, stomach cramps, bending over in pain, having to stop to take a "dump" every 10 minutes for almost three days straight! I can't even begin to describe the smell, almost a mix between molten tar and rancid Thai food.

I brought four rolls of bathroom paper. I ran out by lunch on day two. So, boys and girls, never, I mean NEVER try to eat something new, much less spicy before a multi-day trip. The girl? She stayed with me after all that. No idea why, but she did.

Worst Thing Done on a Date FactsShutterstock

12. Plot Twist

I went out with a guy and we ended up going shopping at the local mall. All the while, he is really sweet and hugging/holding me. After about two hours there, we run into someone who is apparently his current girlfriend.

Young couple in love at train station.

13. A Fork Of A Time

I had a friend who took this girl out to dinner for a first date. It was a disaster right from the start as this girl spent the entire date on her cell phone. Being the nice guy he is, he just decides whatever we'll get this date done with and never call her again. At one point he gets up to goto the bathroom and on his way back, notices her sweater had fallen off the back of her chair.

He bends down (putting one hand on the table for support) to pick it up and feels a sharp pain run through his hand/arm. He looks up and she had stuck a fork into his hand and, while still on the cell phone, simply goes "oh it's you" and continues her phone conversation. He found the waiter, paid for his half of the meal, and never looked back.

Worst Dating Horror Stories Factsgetty images

14. You Kiss Yours With That Mouth?

I was on a date at a college basketball game years ago when there was a bad call on the ref's part, and the guy I was with yelled out something like, "You screw your mother with that mouth?!" Everyone around us got quiet and turned around to get a look at the guy who just yelled that. There was no second date.

Secondhand Embarrassment FactsPxHere

15. No One Likes A Tourist

I once went out with my mom and one of her friends. She kept flirting with the young Hispanic waiter. When he asked us what we wanted to drink, she said "agua" really exaggerated-like and then turned to us and said, "it's Mexican for water". Cringe. That was only one of the many things she did. She also kept talking about how handsome Hispanic men were any time he was around. She was at least twice his age. I actually found the guy after we were done and apologized for her behavior...

Secondhand Embarrassment FactsShutterstock

16. An "F" For Effort

My dad came with on a field trip back in elementary school. We had an admittedly attractive substitute teacher that day, and she was introducing herself to all the parents. Sub: "Hello, I'm Miss Fine" Dad: "Why yes, you are". She immediately just walked away.

Really That Stupid factsWikipedia

17. Love Smack

I took a girl who I really liked on a first date to the movies. The movies were probably a bad choice because I couldn’t take my eyes off her. During the movie, I noticed she had a piece of hair hanging down in front of her face. Me, being the gentlemen that I am, saw this as an opportunity to be cute and go in for the kiss.

Screw me, was I ever wrong...I thought to myself, "I’ll reach over and move her hair out of her face which will then lead into the kiss and it’ll be cute". So, I lean in and reach over to move the hair from her face and make my ‘smooth move’....and as my hand got to within 6 inches of the target zone she comes out of absolutely nowhere, reaches up, and moves the freaking hair herself!!

So at this point, I’m 90% committed, hand located somewhere in front of her face, with no clear objective, and not to mention, obviously blocking her view of the movie. I immediately become nervous and I’m having second thoughts about my decision, but I’m a committed and confident guy who doesn’t back down from a challenge.

But at that moment, all logic froze, and my cute plan dissolved. There was no purpose for my hand anymore, yet it was still on a collision course with her face and for some reason, I couldn’t stop it. I reached over and wiped her forehead, taking whatever makeup that was there with me. Leaving her with an obvious stripe on her forehead that was most noticeable during the brighter scenes, lighting up the movie theatre.

She looked at me horrified. She didn’t even have it in her to ask me what the heck I was thinking because she was so shocked. My entire world turned to flames and the room got considerably hotter. And I didn’t get my cute first kiss. In fact, I got a deleted number...

House M.D factsShutterstock

18. I Scream, You Scream

I worked at an ice cream parlor that was kind of old-timey. Not much seating. Anyway, the guy comes in with a girl, they pay for their own cones and take a seat at two of the seven stools. Dude is talking and the girl is laughing and into it. TWO HOURS LATER, DUDE IS STILL TALKING and the girl looks like she wants to cry or punch him in the face.

They withstood the gale-force trauma of at least seven families with screaming kids, adults who "just love that these tiny places still exist," and several rounds of me sweeping around their feet and pointedly scrubbing the counter around them. The guy never asked her a question. Never let her say more than a few words before he stomped out her "rude interruptions".

I was all, "Hey guys, we close soon. I hope you have a nice day, but I need to mop". Watched them walk down the street and he was STILL TALKING. Like, get a room with yourself, guy. You're obviously the man of your dreams.

Weirdest Date FactsShutterstock

19. An Awkward Coincidence

On my first date with my wife, we started talking about tattoos. I have a rule that if I have an idea for a tattoo, I sit on it for a while to see if it’s something I truly want. I mentioned this to her and explained how glad I am that I do this because otherwise I'd be covered in Tool (the band) tattoos or some, "other dumb stuff".

Little did I know, I'd just messed up big-time. She rolled up her sleeve to show me that she had the lyrics to one of their songs tattooed across her arm. Oops!

Married Men Dating Facts Flickr,Roxie Rampage

20. To Be Fair, TV Is Pretty Complicated

A girl my dad dated for a while. Even while dating her, my dad would say she was dumber than a bag of rocks. One day, she sat down to watch a movie with my dad. The movie was all about this guy and his twin brother. She sits and watches the whole thing, no interruptions. At the end, she turns and asks, "So there were two of him?"

Dumbest Person FactsShutterstock

21. This One Hurts

I worked with this girl at a Ruby Tuesday restaurant. For her birthday, we all went out for drinks. We were all friends and I think she knew that I liked her at the time, though I hadn’t made a move yet. She gave off this rocker vibe. She had tattoos and dyed hair. She loved 80s hair, metal, and rock music in general. So, for her birthday, I decided to burn her a CD of all of my favorite songs from that genre of music.

I decorated the CD cover with a sharpie and made it look really cool. I wrapped it up with fancy wrapping paper and a bow and gave it to her at the end of the night. I didn’t wait for her to unwrap it, partly because I was still nervous about her reaction to my gesture and partly because I didn’t want to put her on the spot while we were out amongst friends.

Cut to next week. There was a day that I was off and she was working. A close buddy of mine from high school also happened to be working that day. I came in the following day for work and he immediately pulled me aside. He said, "Dude, you should just forget about her". He went on to tell me that she had basically just trash-talked and made fun of my gift behind my back.

Apparently, she had said to my friend, "I can’t believe he did that, I don’t even like the Kills!" My friend and I are really tight and he’s very outspoken. He proceeded to defend me, saying: "Are you kidding me? You should be so freaking lucky and thankful that anyone gives a darn about your birthday at all!"

As soon as I heard about that incident, it immediately destroyed any and all interest that I’d ever had in her. How can I possibly be attracted to someone who cares that little about other people’s feelings? She never even bothered to thank me for the CD at all. She just never mentioned it, so I decided to move on with my life and forget about her.

Romantic Backfired FactsShutterstock

22. When You Gotta Go, You Gotta Go. Hard.

20-year-old me went out to dinner to meet her family for the first time. Got dressed up in nice khakis and a sweater. In the middle I farted but ended up pooping my pants with liquid ooze. There was no hiding the smell, as well as the HUGE FREAKING STAIN ON MY PANTS. It was awkward for all those involved.

Childish Behavior From Adults factsShutterstock

23. Dinner With A No Hit Wonder

I work at a dinner theater. We usually do proposals where we set up a "random draw" where the "winner" comes up on the stage to win their prize and are then surprised by their partner, who proposes. It's usually sweet and makes everybody in the room all fuzzy and warm. Emphasis on "usually". On this night, everything that could go wrong, did go wrong. 

This one guy wanted to take it further, and requested to perform a song—he brought his own music and everything. We're pretty easy-going at this job, so we agree to let him do it. We do the fake draw, the woman comes up on stage in front of a room of 400 people, and the music starts to play. Apparently, this guy was a little nervous, and he compensated by having a few drinks.

So what follows is a messy performance of a song written by this guy that seemed to focus on how he was sorry for cheating on this woman with her sister, and at the end of it, he gets down on one knee and proposes. Usually this gets a round of applause, encouraging the person to say yes, but not after that train wreck of a performance.

The poor woman was just holding her face the entire time and starts shaking her head and says, "No, what's wrong with you?" She storms off and leaves him and our stage manager on stage to a bunch of murmuring from the audience. The only thing our stage manager can think of to say on mic is, "Well, that's that".

The guy ended up staying for the rest of the show and had many more drinks. That was years ago, and it still remains one of the cringiest things I've ever seen.

Cringeworthy DatesPixabay

24. Cat Conversation

It was a speed date. He talked about his cats, all of them he had ever owned in his life, for the entire five minutes. I'm not sure he even asked my name.

'Bla' written on a glass.

25. A Slight Change Of Plans

I had been dating this girl for several years. Let's call her "Ann". We met while working at the same company and things were going really well between us. So well, in fact, that I thought that it was time to pop the question. So, after asking her dad for permission, I planned a whole romantic evening for her, which was going to culminate in me pulling out a beautiful ring after dinner at a very nice restaurant and surprising her with my proposal.

So the big day finally came. Ann looked crazy nervous throughout the whole dinner, but I assumed she just knew what was coming and was feeling anxious in anticipation. As I said, things had been going really well between us. After the main course and before dessert, I got down on one knee in the middle of the restaurant and proposed to her.

Then she said no. That was bad enough, but when she told me why, I nearly exploded. Apparently, she had been secretly dating my co-worker for several months and was planning on breaking up with me, which she proceeded to do right then and there. In front of the whole restaurant. And then she left. The waiter gave me a free dessert.

It was still pretty brutal.

Romantic Backfired FactsShutterstock

26. Everything Stays In The Family

I ended up going back to his house where he lived with his father. In the middle of the night, I farted so loud I woke up him, myself, and his dad. Because you can't be blamed for anything you do whilst sleeping, I just stayed as still as possible. When we emerged from the bedroom in the morning, running into his dad, he said, "Son, you woke me up with that one last night!"

Chuckling away. "Yeah sorry, dad, must have been all the beer," replied my date, winking at me. We've been together for three years now and are due to be married.

Worst Thing Done on a Date FactsShutterstock

27. Cupid Goes To Daycare

I was serving a couple probably in their mid-20s. It was Valentine’s Day and they were arguing a lot (probably because it was a chicken wing place and Valentine’s Day). The guy ended up calling me over to the table to calmly ask me, in front of his date, "Do you have a high chair or a booster seat since someone wants to act like a darn child?"

I was speechless, she wasn’t. They left soon after that.

Cringeworthy Dates factsGetty Images

28. Overtime Means Double-Time…

I used to work the bar at a restaurant that was walking distance from a very rich neighborhood. One of my regulars was an NFL player who would bring his fiancé in a couple times a month. One day, the fiancé came in alone and already very tipsy. She sat on her usual barstool and started rapid-fire typing on her phone without ordering anything.

I kept my mouth shut because she was already tipsy, and she usually tipped me very well. I turned my back to type in someone else’s order, and I heard someone yell and then the sound of breaking glass. Turns out Mr. NFL player had walked into the restaurant with another woman. The fiancé had picked up someone else’s drink and threw it at his head.

Cringeworthy Dates factsMax Pixel

29. An Idea That Folded

I spent a month and a half teaching myself how to make origami roses because my girlfriend at the time liked origami and was not too big on regular flowers. She had said numerous times that she thought origami roses were really charming, so I thought she would definitely appreciate this kind of gesture. What could go wrong, right?

I hid my plans from her as best as I could. I spent hours on YouTube trying to figure these skills out. I wanted to burn my own house down on numerous occasions because of the amount of struggle involved here. Nevertheless, I saw it through and thought that the final product was going to be extremely romantic, awesome, and worth it.

I made 12 flowers, each with stems and leaves, and each one a different color. When I was finally done, I put them all into a vase and presented them to her. Her reaction was about the equivalent of a shrug and a "That’s nice". Pretty much zero appreciation or recognition of how much I had put into this. I would also like to point out how ridiculously difficult origami is, and that I have nothing but the utmost respect for people who do this proficiently.

If you are good at origami, hats off to you and I hope that it came more naturally to you than it did to me. I literally wanted to play in traffic for the duration of trying to learn this. That’s how difficult and frustrating it was for me to learn. It's amazing how something so seemingly simple can be so impossible to execute. I only wish my girlfriend would have felt that way too…

Romantic Backfired FactsFlickr

30. When Ghosting Is The Kinder Option

Immediately after the date, I spent 20 minutes complaining via WhatsApp about how bad the date was. I thought I was talking to my friend with the same name as my date. It was my date and not my friend. I felt bad about it for weeks.

Worst Thing Done on a Date FactsPxHere

31. Car Trouble

Well, I once asked a girl out back in high school by writing her initials with flowers on her trampoline. I did it overnight, so I expected a reaction the next morning. Reasonable, right? Wrong! See, I had left a note on her car suggesting that she check her trampoline, but she just so happened to have driven her mom’s car to school that day instead.

She even went out for lunch that afternoon and still said nothing when she returned, so I was in full "what the heck have I done to deserve this silence" mode until I realized that she had taken the wrong car. Thankfully, her mom called her in the middle of the day and told her that she needed to come home early for some reason or another.

Before she left, I spoke to her for a couple of minutes and she said we could talk more later that night. I thought this would be my chance for sure. Fast forwards to that night. No response from her to any of my calls or texts. After a while, I finally gave up and went to my buddy’s house to hang out. That was when I realized why she hadn’t been responding to me.

She was over at my buddy’s house, clearly together with some other guy. Since I had never told anyone about my feelings towards her, I then had to spend the rest of the evening pretending it was nothing while silently feeling crushed inside. I played my worst game of pool ever before breaking my friend’s phone after he questioned whether I would seriously do it. I wanted to prove to her that I was serious about whatever I say.

I ended up driving home with sadness level ten.

Romantic Backfired FactsShutterstock

32. Should I Take Your Word For It?

I had a very pretty friend of mine from college stop in town and call me to catch up after work. We go to happy hour and she starts talking about how she has only slept with one guy and she wants that to change. She then goes on about how her friend I had slept with had a very high opinion of me.

We put back a few drinks and then I left because I had to get up for work the next day. I told her she was really pretty and shouldn't have any trouble hooking up with a guy of her choosing. A year later it dawns on me...

Most Embarrassing Flirting Fails Factsyoutube

33. Duty Calls For Everyone

I work at a restaurant. I had to watch my boss wait on a couple having a romantic candlelit dinner. The "date fail" part? It was his ex-girlfriend and the guy she cheated on him with...

Cringeworthy Dates factsGetty Images

34. One Wild Ride

After a date, I dropped the girl off in the parking lot where her car was parked. We said goodbye to each other and parted ways without a kiss, as it was our first date. As she got out and began walking across the parking lot, I suddenly got the courage to whip my car around, stop it right in front of her, get out, and kiss her.

In my head, it was going to be like something out of a movie. In real life, it was a complete disaster. I pulled up to her, forgot to put the car in park, got out, walked away from the car, watched her look at me in horror and point, turned around, and ran towards my car as it slammed into another parked car. Just a typical day in my life really…

Mistaken Identity FactsShutterstock

35. What Are You Trying To Tell Me?

One time, I wanted to do something romantic for my girlfriend. So, I decided to sign her up for painting lessons as a surprise present because I knew that she was getting into painting. She took the gift to mean that I thought her painting sucked. She never took the lessons, and I never got my money back either.

Seymour Fleming FactsShutterstock

36. A True Gentleman Wastes No Meat

We went for burritos. I'd never eaten burritos before, and what I didn't realize was that there's definitely a wrong way to do it. There's planning involved. Toward the end of the burrito, I felt something slip in the structure of my meal. It became clear that the burrito was going to slither into an unwrapped state imminently, the tinfoil it was wrapped in wasn't going to stop it, and I had a choice.

I could either watch my tasty treat of cheesy beef flop onto the floor, or I could eat it, all of it, right now. I didn't regret my decision; but I did have enough of a vague sense of dignity to vocalize a muffled "fffwrrry" to my date as I fished tinfoil out of my packed and leaking gob, and used the other hand to wipe a stray fleck of beef that was oozing down my beard.

To compound the awkwardness, it must have been a full minute and a half of silent heavy breathing through my nose before I could clear my mouth enough to more thoroughly apologize and explain. I don't know if she agreed with my choice; but I think she respected it. The thing is, there was actually a second date, and a third, and I think a fourth.

No matter how disappointing you are, gentlemen of Reddit, sometimes a lady will be in a dry spell longer than your own. Or possibly have a thing for fat scruffy men suddenly and inexplicably shoving an entire burrito into their already-stuffed and dripping maw, I never quite ruled that one out.

Worst Thing Done on a Date FactsShutterstock

37. Tapped The Glass Too Soon

When I was waitressing in college, I witnessed the single most embarrassing thing to happen to a person to date. Right in the middle of their dinner (and in the middle of our Friday night dinner rush), this poor guy stands up, taps his wine glass to get everyone's attention, and then proceeds to tell EVERYONE what a fantastic person his girlfriend is, how much he loves her, and how lucky he is to have her in his life.

The whole time this is happening, she is just sitting there watching him with the most boring look on her face. It was so weird. Kind of like, "Yeah, tell me something I don't know". Then the poor guy pulls out a ring, gets on one knee, and asks her to marry him. She gives him the most disgusted look imaginable and says, "THIS is the ring you expect me to say yes to? Are you stupid? Could you be any cheaper?"

Then she gets up and walks out, leaving the poor guy just kneeling there.

I didn't charge him for the meal.

Cringeworthy Dates factsGetty Images

38. Dinner Is Served

To celebrate our fifth Valentine's Day together, I was going to recreate our ever first meal together over candlelight. It was chicken patties with marinara sauce and mozzarella melted on top, along with pasta and a Dole bagged salad. In the days leading up to it, when she asked what I was going to do, I told her I was going to make a special meal. Her reaction broke my heart.

She laughed and said, "You’ll probably just make the same food we had years ago or something dumb like that". Needless to say, I had to change to plan B. For the record, my wife is a very sweet lady. She was laughing about me being predictable, not just trying to be mean or hurt my feelings or anything like that.

Anjelica Huston FactsPixabay

39. Under Pressure

I cooked a romantic Valentine’s Day dinner for an ex of mine back in 2002 or so. I was making some sort of chicken dish. I put it in a saucepan to cook. Meanwhile, my girl and I were hanging out in the bedroom while it was cooking. Let’s just say we got a little "preoccupied" for the next little while. Then, a few minutes later, I suddenly thought "Uh oh, the chicken!" and went running downstairs to check on it.

I ran into the kitchen in my birthday suit and grabbed the lid off. Apparently, I had unknowingly used my roommate’s pressure cooker. I didn’t actually know what a pressure cooker was at the time, but I definitely do now! I forced the lid open and got boiling water all over my stomach, arms, and private area. I spent the rest of that Valentine's Day in the emergency room getting burns treated.

Romantic Backfired FactsWikimedia Commons, Jan-zidek

40. The Bad Move Was Listening To Mother

In the 90s I managed a busy furniture store with lots of customers. As an attractive girl in her mid-20s (and not wearing a wedding ring, as I wasn't married) I definitely got hit on. Frequently. We sold a lot of mattresses so that alone lent itself to many awkward exchanges for me. One day I had a customer, a lovely lady in her 50s who I spent a lot of time with in the store.

As we were finalizing her invoice, she went on and on about her son who had just moved into town (from near where grew I up) and how I really needed to meet him. She explained how attractive he was (she also told me about his schooling and job, but really pushed his physical attractiveness) and after much badgering I agreed to meet him on a very blind date.

We talked on the phone (probably on landlines, this was pre-cell-phone era!) and met at the pub. I felt my stomach drop. He was one of the most physically unattractive men I've ever met. What she described and what I met were not in the same universe let alone ballpark, at least to me. So, I talked with him for a bit but unfortunately talking to him was like wrestling wet cardboard.

I'm a sucker for a sarcastic, witty guy and no matter how he looked, if he had been a bit cocky and had a sharp sense of humor, he could have won me over. But no. So, I tried for a few hours to make some conversation and realized it wasn't happening and so I found an exit point and used it. I didn't just bolt on him, I did give an excuse to leave, but at that point, I learned that MOTHERS WILL ALWAYS THINK THEIR SONS ARE GODS no matter what the kid looks or acts like. That was the first and last time I was ever "set up" by a relative stranger.

Real Life Experiences Didn’t Live Up to Disney Movies factsShutterstock

41. Do You Really Want To Hurt Me?

One day when I was in kindergarten, there was a girl who I had a little crush on. At least as much of a crush that a five-year-old can have, I suppose. The teacher summoned us to the floor area, where she sat on a chair to read to us. I wanted to sit next to said crush, but she wanted to sit next to her friend. What did my rational five-year-old mind do?

Cry. Yep, I bawled my eyes out because she didn't want to sit next to me. Naturally, the teacher stopped and asked me what was wrong. After my blubbering story about her rejecting me in front of the whole class, she forced the girl to let me sit next to her.

Parenting Lessons BackfireShutterstock

42. Always Destroy The Evidence

One of my best friends had a radio show on our university's station. I liked a guy in one of our classes, and my friend and I thought it would be clever for him to interview me off-air about my interest in that guy. We then put the interview on a disc and gave it to him. Well, the feeling was not mutual. I graduated five years ago and I'm married now, but this still makes me cringe so hard.

Wendy Williams factsShutterstock

43. The Calm Before The Storm

It was 18 days before our wedding and we were really stressed out about it. So, I left work early, got a bunch of things, cooked dinner, set up a little scavenger hunt of memories to remind her of why we were together in the first place, and then led her over to the dinner table with her favorite meal and candlelight ready and waiting.

She then broke up with me and made up some kind of bizarre excuses as to why she was doing it.  And I found out a few weeks later that the reason we were having trouble and stress in our relationship was not related to wedding planning. It was because she had been seeing someone else on the side. So much for that gesture!

Change Life FactsShutterstock

44. You, But With A Woman’s Touch

My buddy tried hitting on my sister. "I always thought it would be cool to have a chick that's a female version of [my name here]". Swing and a miss.

Disrespectful at Home FactsShutterstock

45. Missed Opportunity

I was on a first date with a girl and I also worked with. We'd been flirting for weeks and had wonderful chemistry. Our date was great and had a life of its own. She drove. At the end of the six-hour long date, we were sitting in her parked car in front of my house, continuing the captivating conversation. We had a work meeting the next morning, so when it came time for me to go, I started to exit the car and said "See you tomorrow".

She sheepishly said, "I can't wait that long". Without thinking, I replied, "Well, you're gonna have to" and slammed the car door. I didn't realize what she meant, or how what I said came across, for some time, like the next day.

Boyfriend with camera phone photographing girlfriend driving truck.

46. My Fight In Shining Armor

I was going on my first date with a dude. I told him I had a 3-hour window to hang out. He proceeded to suggest a coffee shop, but upon arrival told me he hated coffee and the atmosphere of coffee shops. Cool. So, I suggested an art museum or bowling. He said he brought no money because he doesn't pay for dates on principle. That's when I should have known this guy was bad news. But nope, I'm an idiot.

I offer to pay but he won't have that either. So, I suggest a walk around a nearby lake. We have the most one-sided conversation of me asking questions and him giving one-word answers. When we got back to our cars (an hour later) I told him he didn't really seem like he was into me and suggested we cut the "date" short.

The dude BLEW UP. "You said you had 3 hours and it's only been an hour, you liar! You have 2 more hours! Our date is supposed to last 2 more hours". Fine dude. It's a beautiful day and if you want to do two more laps around the lake then by all means. I talked about any little tidbit that entered my brain, like the chick from HIMYM.

"Do you think when a porcupine walks through the woods his quills act like giant whiskers and he's just constantly getting poked anytime he bumps into something? I ate a kiwi whole once and my mouth felt really fuzzy after, actually I ate a random leaf one time and my whole tongue swelled up let me tell you about that."... I never heard from him again.

Worst Thing Done on a Date FactsShutterstock

47. The Jig Is Up

So back when I started learning how to flirt, a few prior successes made me decide to try my luck with this intimidatingly hot girl. So I walk up to her brimming with confidence, tap her on the shoulder, she turns around and I said "Hey" with a raised eyebrow. She's looking unimpressed so I follow up "Why would a girl like you feel the need to hide that pretty brown hair?" (her hair was black at the time).

She's smiling, now I've got this. She gets really close to me all giggly and bright eyed asking how I knew her hair was brown. Her hotness shatters my false confidence and I start mumbling about her having freckles, genetic impossibilities, and deductive reasoning... it was all downhill from there. Nailed it.

Most Embarrassing Flirting Fails Factsthe modern man

48. Turning To The Feet

Was set up on a blind date by a coworker. Things went reasonably well—ok conversation, he seemed to be genuinely nice. My co-worker and her boyfriend double dated with us for moral support. We went back to the co-worker's house after dinner to watch a movie together. That's when things got weird.

Co-worker and boyfriend left the room to give us some "alone time". Immediately, my date tried to kiss me. It was one of those approaches with his tongue hanging out. I nicely rejected the kiss, saying it was too soon for that type of affection for me. So he shifted his attention to my feet. I was wearing open-toed shoes and he grabbed a foot in his hand and asked if he could rub my feet.

I declined and he began to beg. Told me that he loved feet and would love to suck on my toes. I declined again, started to get a bit scared. He made a last ditch effort by asking if he could just sniff them once. I gathered my things and left ASAP. He followed me to my car and tried to beg me in a baby-talk voice to come back, me and my "widdle piggies" (toes).

I kept expecting a camera crew to pop out from behind a tree proclaiming that I had indeed been "punk'd". I was as nice as possible about everything, citing that I just needed some time to get comfortable with someone before becoming affectionate. I pulled out of the driveway in such a hurry that I squealed my tires a bit.

I had no intention of seeing him again since he had violated my personal space so much. I (probably wrongly) passive-aggressively ignored his phone calls and myspace messages. He couldn't take a hint though, and called 20 times in one day. I finally manned up and told him that I wasn't interested in pursuing a relationship. He immediately got nasty, called me a tease, and told me never to contact him again. Weirdest date ever.

Attractive girl making mimic and facial expressions.

49. Well, That Was A Bold Move...

Not me, but a guy I sort of had a crush on totally failed at trying to flirt with me. We had been flirting and bantering back and forth for months and nothing ever came of it. But one day I ran into him when I was shopping at the grocery store he works at. We had not seen each other in like six weeks at this point so we hugged and made small talk.

As we were hugging to say goodbye he turned his head and full on licked my face. It was incredibly strange.

Most Embarrassing Flirting Fails Factsfullmag

50. A Change Of Plans

During my sophomore year of high school, I was pretty involved in my school's drama department. Yeah, I was a lame kid, I know. There was a girl who I had befriended the year before who was now a senior, and this was all back when I was naïve enough to think that grand and bold romantic gestures were a good idea.

So, I basically got most of my class in on the gig: asking her to be my date to the homecoming dance. I had two main ideas, the first being pulling a 10 Things I Hate About You and getting all my friends to help me serenade her with "Can't Take My Eyes Off Of You". Luckily, one of my friends in her year talked me out of that one.

Instead, I had the bright idea to have my friend hand her a parcel addressed to the "Most Beautiful Girl at (insert high school name here)" as she walked into class. I signed my name on the parcel and stood by waiting with a bouquet of roses for when she showed up. Inside said parcel was a hand-mirror with the word "Prom?" written on it.

Well, uh, that didn't work out quite as planned. I mean, she was nice about it. She pulled me aside and explained how she appreciated the gesture and how it was the most romantic gesture anyone had ever done for her. She then explained that she had already made plans to go solo with her best friends. And she did, and ended up dancing with me for most of the night anyway.

But, I mean, definitely was not the ideal outcome.

Bad idea signShutterstock

51. Who Done It?

I made a huge plan to ask my crush out to prom. I made a bunch of very large signs and placed them outside of her house, asking her the big question. Unfortunately, I stupidly didn't put a name on the signs saying who did it. Well, it turned out that her next-door neighbor had a crush on her too. He took full advantage of the situation and acted like he was the one who had put the signs up to ask her out. She said yes to him.

Nobody believed me when I tried to tell them that I had actually been the one behind it. Oh, and on top of that? They're now married.

Make You Smile FactsPxHere

52. ISO Deoderant

In 8th Grade, this girl asked me out after we danced together at a dance. I was pudgy and horribly hormone-ridden, and she wasn't hideous, so of course I said "yes" (mistake number one). We decided to see Houseguest, starring Sinbad (mistake number two). So she and her dad come to pick me up, and we go to get tickets, it was at this point in time that I noticed that this girl, we'll call her Carly, seemed to have a bit of BO.

It wasn't terribly obvious, more like a "sweaty shirt that hasn't been washed in a day or two" sort of way, but when you got close, you could get a whiff of something. Still, 8th grade here, I wasn't going to complain too much, so I bought Carly some popcorn and we sat down in the back of the theatre. I don't know how many of you have seen Houseguest, but it's horrible. Soul-crushingly, heart-achingly horrible. So horrible, in fact, that we can't even make out, because the whole situation is just awkward.

Fast forward to the end of the movie, and it's clear that Carly is angling for a kiss of some sort, so I lean over to kiss her, and I just see this clump of some kinda goop on her forehead (she had brushed her hair out of her face, and I guess it was grimy from the popcorn). That, coupled with the stress and awkwardness was enough to make me retch in front of her.

She snapped bolt-upright back into her seat and we spent the rest of the date in stone silence, including the drive home when her dad was asking us how the movie went. To this day the memory can ruin any steamy situation.

Young couple watching a movie at the cinema.

53. Make A Run For It

Back in primary school, I had a crush on a girl. Her younger brother was kind of a friend, so I'd hang out at their place every once in a while. But thinking it would be weird to ask if I could hang out, I'd go for a run past their place and hope they'd notice me and invite me in. It worked, but most times I had to turn back and run past at least 4 times before they'd invite me in.

I wonder how many times they actually saw me doing this.

Surrounded by Idiots FactsShutterstock

54. VIP Dinner

I dated a girl for three years in college and lived with her for two of those years. Her father had never liked me and never really talked to me. I was a year older, and after graduating I stayed behind a year to live with her while we figured out our future. The week of her college graduation, her extended family was in town to celebrate.

They had two fancy dinner reservations two nights in a row. Work prevented me from going the first night, which I was invited to, but the second night I hadn't been invited. My girlfriend called her aunt, who had made the reservations, and was told it was an oversight and of course I could come. That…did not turn out to be the case.

The night of the dinner, my girlfriend’s mom and dad show up to pick her up. I walk out with her and we get in the car. Her parents were obviously whispering very quickly with each other as I walked to the car, then they say "Uh... so you're coming? We only had reservations for a set number". My girlfriend explains how the aunt added one to the reservation, and we get in the car and start driving.

My girlfriend had brought along some picture albums to show from a trip, and they were too big for the back seat where we were, so we stopped a ways down the road and I got out and put them in the trunk. As I'm out of the car, I see that the father is talking very fast to my girlfriend and her mom. I get back in and the father starts driving super slow.

Finally, he stops at a stop sign, puts the car in park, and turns around to look at me. He says "This is a family dinner. You aren't family. You weren't supposed to be invited". I sit there in silence for what seems like forever but was probably 15 seconds. I say "Uhh…should I get out of the car?" he says "Yes".

I get out, and he speeds off. I then walk home. As it turned out, they never made it to dinner. My girlfiend stuck up for me, and her father hit her. He said she had to break up with me or he'd never speak to her again. And he was the kind of guy to follow through on that sort of thing; he had already cut ties with most of his family for stupid reasons.

The next day, she graduated from college, came home, and broke up with me.

Tipping Point in Relationship factsShutterstock

55. So Much For The Language Of Love

My sister was on a first date with some guy she met online and was nervous, so she had my significant other and I meet up with them. The guy was super braggy about being able to speak German, not knowing that my S.O. was raised there and speaks it fluently. So, my S.O. tries to start a conversation with him in German. The guy apparently only spoke a few words of German and left embarrassed and without any chance of a second date. My S.O. still feels a little guilty about it.

Secondhand Embarrassment FactsShutterstock

56. Winner Loses

The first time I had a flirting fail was many years ago when I would walk to my work a couple miles away from my place. A girl I worked with offered to give me a ride, even though I could clearly already see my destination from where I was. She was persistent; as was I. I won out, but came to find out, I had truly lost. She wanted to give me a ride specifically so she could get romantic with me in the car.

Most Embarrassing Flirting Fails Factssportshestfysioterapi

57. Haul Away

I wanted to pick up my new girlfriend for a romantic evening, but my car suddenly broke down. She was the girl of my dreams and I was very concerned that this would ruin our evening. Unfortunately, me being underage at the time, I couldn't rent a car. However, I soon discovered that I could rent a U-Haul truck! It would cost just 20 dollars a day plus a few extra dollars for the mileage. What could go wrong, right?

So, I rented a U-Haul and was on my way to her house to pick her up for what promised to be the most awkward date of her life; until I pulled up, that is. Once I arrived, I saw her family moving boxes from storage, and they had a lot of stuff. Like, a lot. As soon as they saw me pull up in that truck, they thought I was just the greatest help.

So, instead of the romantic evening I had planned, I had to spend the next few hours helping them move boxes. No date for me. But we're engaged now, so I guess I can’t complain!

Romantic Backfired FactsFlickr

58. Daddy’s Little Girl

The most awkward thing to ever happen to me is still something I have a hard time thinking about. This girl called me "Daddy" during an intimate moment…all with a picture of her lifeless father staring at me on the wall.

Online Friend FactsShutterstock

59. Didn't See That Coming

I had been invited to go with a friend to Chicago. We brought along a friend of hers, but someone I hadn't ever met. He was a cute guy though, and we talked a lot, had a lot of similar interests. At one of the museums in Chicago, my friend wanted to go see a deep sea movie, and I... can't do anything deep sea.

Her friend offered to stay outside with me so we could both go look at the Lascaux cave painting exhibiting, which was VERY exciting to me. It wasn't all just about the cave painting, but about ancient life, knapping, hunting, the way they made things, etc... So I, not being able to control myself because I have zero social knowledge and I'm also yeehaw country, at the exhibit about hunting specifically, ask this very cute guy I am very interested in if he knows how easy it is to skin a deer.

He looks at me. I look up at him and keep. Going. My brain is screaming at me to stop but it has no control over my stupid honky mouth. "Simple as getting a truck, a knife, a rope, and some rocks! You cut around the neck, make a kind of ruff, and tie the rocks into that? Then you tie the other end of the rope to the truck and drive slowly forward. It comes off like a sweater!"

Lord knows why, but that weirdo dated me and married me instead of running for his life.

Most Embarrassing Flirting Fails Factsceritapic

60. She Should Have Been More Patient With Her Response

So I'm a nurse and there was a coworker I was crushing on pretty hard. He had a bottle of Diet Coke or something similar at work one day in which he took one sip out of it, then asked if I wanted to share it with him. However, my dumb self misheard him, and I thought he said that he picked it up out of a patient's room and that he saw the patient take only one sip out of it so it was "barely used".

The thing that I misheard was that he said he took a sip out of it, but I heard a patient did instead. I had no idea he was drinking from this bottle, and I thought he was offering me a random patient's bottle of Coke who went home. I proceeded to belt out "EWW! Heck no! What's wrong with you?!" while laughing pretty hysterically.

He looked so sad after that but I couldn't really understand why until later that night after he went home and I replayed the situation in my head and realized that I completely misheard him.

Most Embarrassing Flirting Fails Facts

61. Too Much To Bear

I was seeing this girl for a while and decided to ask her to be my girlfriend. To be romantic, I went to Build-a-Bear and had a teddy bear made with a voice recording of me saying "Sara, will you be my girlfriend?" inside of it. I then went to her house, gave it to her, and asked her to press the bear’s hand so that the message would play.

When she heard the question, she politely declined because she wasn't ready for a relationship. But the story gets so much worse. Her family happened to have been having a party in the background while all this was going on. And yes, somehow, it gets worse. While I was still standing at the doorway, her eight-year-old sister who loved stuffed animals saw the bear and walked over towards us.

The kid grabbed the bear out of Sara’s hands and began running around the house pressing its button repeatedly. As a result, her whole family and all their friends then heard my desperate and rejected request getting replayed over and over again. After a couple of minutes, I couldn't bear to hear my voice asking her out anymore, so I quickly left.

Snobbiest Behavior factsShutterstock

62. Me-Ow

I was at a bar with the girl I'm dating and her roommate when I received a text from a good female friend of mine from high school: She was in town and wanted to meet up. I invited her to join the three of us for drinks. When she shows up, she gives me a big hug and starts talking to me intently. My date's roommate quickly misinterprets the nature of our friendship.

She looks at my high school friend and says right out, "I think it's pretty obvious you aren't wanted here, so you should probably leave". Now, my date and I looked at her in disbelief as if we couldn't believe that just came out of her mouth. My friend, however, was quick to respond. She downed her drink, stood up from the table and said, "Well you're fat and ugly, so I win," and walked away.

Awkward Moments FactsPxHere

63. Let’s Split The Check And Literally Everything Else

I guess you could call this a couple date. I was working at a fancy bar when a married couple sat down on a pretty slow night. I went over the specials and they ordered. Once appetizers came out, the man thought it would be a good idea to serve his wife divorce papers. I did my best to avoid that side of the bar. I did bring out tissues for the wife, who was breaking down.

I ended up boxing up the dinner. The guy paid, but I do not envy that ride home.

Cringeworthy DatesFlickr

64. Mother May I

I had been friends with this guy for nine years. We were both sophomores in college, and he was home for Christmas break staying with his parents. We had recently discovered that we had feelings for each other, but decided we didn't want to date long distance. But, while he was home, we wanted to spend time together.

We were with a group of friends but decided to go back to his house, just the two of us. He had asked his parents earlier in the day if he could have friends over. Well, his parents already disliked me. My brother had dated their daughter and broke her heart. Whoops. So I show up at their house, with them expecting a group of people, and it's already awkward.

Then, my friend and I spent a couple of hours in his basement making out. By this time, it was pretty late (around 1:30 am). He went upstairs to get his keys to drive me home, and when he came back downstairs his eyes were really wide, and he said, "I'm so so sorry!"

Apparently his mother was still awake and refused to let him drive me home that late. So, she decides it would be better if she drove me home. It was a 20-minute drive, and the car was completely silent.

Awkward Moments FactsShutterstock

65. Business Affairs

I once surprised my fiancée at her work with a bouquet of flowers. She thought it was creepy and told people I had snuck into her office. Security had to change all the codes as a result of this. In reality, I had simply walked up to the receptionist and said I had a delivery for my fiancée, at which point I was politely escorted inside.

At first, I couldn’t figure out why she had reacted like that to my gesture. Then, I found out the disturbing truth. It turned out that she had been having an affair with her boss and was gaslighting me to make me look like the bad guy. At that moment, it all clicked for me because I’d always thought "the only difference between a creepy gesture and a romantic one is how you feel about the person doing it".

Now I understand that I did nothing wrong.

Biggest Impact FactsPexels

66. Space-ially Challenged

I dated a girl for around four months a few years back. One day, we were chilling at my house, and I asked her if she wanted to watch an episode of Brian Cox's documentary Wonders of the Universe. She declined. When she said why, my jaw hit the floor. Apparently, she didn't believe in space. She was 100% convinced that the sky was all there was.


Science factsPixabay

67. When Nature Calls

When I was 14, I had a boyfriend named George. Being 14, all we ever did was make out and watch movies together, and his dad was cool enough that sometimes we would have some of George's friends over too. One day, George and I were chilling out with our mutual friend Steven, watching TV and whatnot, when his dad walks in and says, "You guys just watching TV then? Well, George, I think I'm going to call Old Mary".

So, about 10 minutes passes and someone comes to the door and they go upstairs. George then turns around and says casually, "Old Mary's a hooker, by the way". The look on our faces must have been rather special. I think we sat through about five minutes of the dodgiest sounding bedroom noises before making excuses to leave... what a messed up father-son relationship. Old Mary.

Online Friends FactsShutterstock

68. So You Think You Can Dance

A friend wanted me to find a date for the formal our fraternity was having. I asked a few girls and they had other things to do. So I called the girl who I usually danced with at a few dances. She picks up the phone, I reply who I am and ask if she wanted to go to the winter formal that was coming up. I overhear her say to her roommate, "It's that stupid boy who always asks me to dance". She agreed.

Fast forward a few months later, and I got introduced to her roommate. As soon as I can, I tell her, "I was the stupid boy who kept asking your roommate to dance".

School Trips FactsShutterstock

69. It Runs In The Family

Back when we were 17 or 18, my boyfriend and I were in his room one day, just watching movies and chilling. His mom walks in and asks to talk to him, they both go out into the living room, and she proceeds to rant at him about how it's not normal for us to spend so much time together, and how she didn't like that we had been in his room all day.

Meanwhile, I'm alone in his room, and can clearly hear the whole conversation. I gather my nerves and all my stuff, walk out to them, and say, "Matt, I'm going home, would you like to come over to my house?" The mom interrupts with, "We're actually having a conversation here," so I just say goodbye and walk out the door.

His sister, who thought the conflict had somehow been initiated by me, then made it ten times worse. She chases me out of the door screaming, "YOU WITCH, YOU RUINED MY FAMILY!" I was pretty shocked by this and didn't respond; I just got in my car and drove home. A few minutes later, my boyfriend shows up to apologize for his family.

It didn’t end there. A few minutes after that, there's another knock on the door. Yep, his mom had followed us to my house and asked to talk to him outside. He told her to go home. This all happened a few months before we both moved away to university, so I just didn't go to their house again. We're now in our 20s and still together. His family is still crazy and he agrees.

Luckily, we now live five hours from them.

Caution to the Wind factsShutterstock

70. Are You Negging Me?

On a very awkward date, the guy asked me: "So, at what age did you start wearing tampons?"

Twins FactsShutterstock

71. The Fall Of An Empire

Bartending a day shift at an upscale Italian place in a high-end shopping centre over the Christmas season. Couple comes in, starts drinking, and are VERY flirty with each other. They clearly liked the attention. I wasn’t quite sure why the man seemed familiar, but he had a face I knew from somewhere.

Midway through their lunch, the woman used his name, and it dawned on me that the man was the husband of my previous boss. I told him he looked familiar and asked if he was "Mark" from "That Restaurant on the way to the Beach?" He said that he was not. But the woman he was with insistent on making it awkward and peppered me with questions like, "I’ve heard the owner of that place is crazy, did you know her?"

She was backhandedly trash-talking "Mark’s" wife and the whole thing was so uncomfortable. He was an all-around bad dude though and deserved it. For additional context, his family had owned "That Restaurant on the way to the Beach" and his wife (my former boss) ran the place until she caught him cheating. They divorced, she got the restaurant and continued to run it with her sister.

Fast forward a few years, and the two eventually remarry. It was during their second marriage that he turned up at my bar with his mistress.

Cringeworthy Dates factsMax Pixel

72. Love At First Sight

Not me but this story fits and I love it. It was probably 1968-ish and my mom was in high school. She hated cigs because her whole family smoked, but nevertheless she wanted to impress this guy she liked who smoked. So she borrowed a smoke from her sister, lit it and walked over to him. She took one puff and threw up all over him.

That's how my parents met. They were married for 39 years.

Most Embarrassing Flirting Fails Facts

73. Bad Call

I was out one night, and had beyond enough to drink. I went to a cafe next door to the bar, grabbed some food and hung out for a while. This guy walks in. He's kind of cute, so we start talking and I invited him to share my sweet potato fries with me. One thing led to another, we went outside, made out for a while and then we took a taxi back to my place.

Everything seemed fine...until I tried to drop him off the next morning. I asked him where he lived, and he kind of avoided the question, just giving me directions. To the local homeless shelter. He was homeless. And he admitted he was homeless because he just got out of the clink. For assaulting a woman.

I had given him my number before any of that came out, and he called constantly. After a day, I had to block all unknown numbers on my phone, because (being homeless and all) he called from a different number every time. It was miserable, and it took nearly a month for the messages to stop (thank god for visual voicemail).

Man on Cell Phone.

74. Special Day

I was eating at a restaurant and heard the hostess ask a couple she was seating if they were out for anything special. The husband replied, "No, it’s just our anniversary". It has inspired my father-in-law to drop that line almost any time he goes out to eat now.

Valentine’s Day Disasters FactsShutterstock

75. There’s No Accounting For Taste

I dated a woman for about a month. One day, we are sitting on my couch making out. Suddenly, she just stops, turns to me, and says, "I am not attracted to you. I'm sorry". Then leaves. That one was hard to get over.

Family secretsUnsplash

76. Netflix And Not Chill

My brother and a lady friend came inside our house. I asked him where his girlfriend was because her bras were still in the laundry room. He then informed me that they had broken up a month before and that this lady was his new girlfriend. Well, things were about to get awkward. I had already invited his ex over to watch movies with me that night.

When she arrived, everyone stood there in awkward silence for about a full minute. Everyone left pretty quickly. I am a female and didn't know they'd broken up. But why did she say yes??

Henry VIII FactsShutterstock

77. Parental Pick Up

He called 20 minutes before he was supposed to pick me up. Told me he'd be a couple hours late because he wanted to play basketball... the time he was supposed to get me rolled around... no show... twenty minutes later a car pulls up and his mom gets out... (keep in mind we're freshmen in college).

He sent his parents to come get me. 20-minute drive to his house in the car. Alone with his parents. He proceeded to talk about the girl he was in love with for the rest of the date and ended it with an awkward hug stating that it wouldn't work because we lived too far away.

Affectionate couple riding in back seat of car.

78. Feeling Her Brains

I was to meet my girlfriend in a building near midnight for a date. When I got to the predesignated room in that building she directed my attention to a jar on the table. It had a human brain in it. She told me to don gloves and take the brain out of the jar. As I was holding the brain, it seemed very small. I asked, "Is this a child's brain?" She said, "Yes". I felt a shiver run down my spine as I held the weight of the child's brain in my hands.

I started to imagine what this child was like before it passed. What did its face look like? What kind of personality did it have? She interrupted what had become a rather chilling reflection by telling me I had to help her cut up the brain before midnight. We cut into the flesh of the brain that used to hold memories, feelings and dreams.

Now it was cold and lifeless as my date became very attentive to every detail of structure that our knife revealed as we cut the brain apart. When we finished, I put the pieces back into the jar and we left for the rest of our date. She was a medical student and I often had to help her study in our dates. It was the only date I ever had in which I felt genuinely ghoulish.

Worst Dating Horror Stories Facts

79. Dart Of The Deal

Oooh about a decade ago when I used to smoke, I was on the rooftop of a bar with the rest of the smokers when a girl came over. She offered up a dollar for a smoke, which was pretty common. So I said, "I'd rather get your name than your dollar". She replied, "I'd rather just give you the dollar". Ouch. And to make matters worse, it happened in front of everyone I was there with.

Most Embarrassing Flirting Fails FactsThe Best Hair Salon in Cincinnati

80. Check Yes Or No

In middle school, I wrote a love note to a guy in my class who I had a huge crush on, asking if he'd be my boyfriend. He was really friendly to me in the class we shared and always made it a point to talk to me, so I thought he liked me too. He was part of the cool group, though, and I guess I didn't notice that he never spoke to me outside of class.

I walked up to him during our lunch break to give him the note. For some reason, my stupid kid brain decided that passing notes in class was against the rules, so clearly doing it at lunch in front of everyone we know would be better. His jerk of a friend snatched it out of my hand, opened it, and read it out loud to everyone at their table.

They all started to laugh hysterically at me. My crush looked mortified, which I guess counted as a rejection. He never sat anywhere near me again in class, which unfortunately meant that we never spoke again. I was subsequently picked on and made fun of every single day by his group for the next year and a half over this incident.

It was pretty terrible.

Teacher Confiscated FactsShutterstock

81. Guess Who’s Coming To Dinner

I once decided to make a bold move with a close lady friend of mine. I invited her over for a home-cooked meal on Valentine's Day at my lousy college apartment since neither of us were seeing anyone at the time. Pretty smooth move, right? I thought so. So, I cooked a pork loin and some pasta with something or other on the side.

I also purchased an expensive $12 bottle of wine. "She'll be here any minute," I kept telling myself as I waited. At around 9:00 in the evening, there was still no sign of her. I finally decided to text her. Her response made my blood run cold. She told me that she had assumed my invitation was just a joke. That’s definitely what you want to hear in that situation, right?

Believe it or not, she did eventually—albeit sheepishly—show up at my place once I explained that I had actually meant it. I think she was totally surprised and caught off guard. So, even though the initial romantic gesture backfired, the evening wasn’t a complete failure! We are now married, and I remind her of this story every Valentine's Day.

Romantic Backfired FactsFlickr

82. Don’t Be Cruel to A Heart That’s True

Not really a flirt, but I finally got up the courage to tell the pretty girl in my class that I had a crush on her. She told me she needed to think and I went back to my desk, heart pumping so fast I could hear it. She walks over and says, "You wanna be my boyfriend?" "Yeah!" I said excitedly".

Ok, well now I'm gonna dump you". I look over and her friends are snickering in the corner while she laughs in my face and walks off. Didn't ask out another girl for years. Secretly thought all girls were horrible for a while. Feels bad man.

Most Embarrassing Flirting Fails Factspinterest

83. The Cover-Up

In seventh grade, I had just started watching more anime on Toonami and was really into it. Like, creepily into it. One day we had to do a paper describing ourselves coming back from summer break and the class had to put a person to a description. I named my favorite jacket that I wore every day "Takeshi" for God knows why.

Then the cutest new girl in the class read my description out loud, and in it I described the love for my jacket and how I had named it what it was. The cute girl looks weirded out, stares at the class and goes, "What weirdo names their jacket?" Once no one guessed who it was, I piped up and said: "Well maybe they aren’t here today?" I was obviously trying to cover myself.

Except I forgot that this was an IN-CLASS ASSIGNMENT. So the teacher said, "No, it had to have been written by someone here?" Finally one of my friends goes, "Hey, aren’t you like the only one in class who plays soccer?" which was also written in my description. I sunk in my seat as we moved on to the next description...I wake up sweating, feeling that jacket still on my shoulders...

Scariest Things They've Woken Up To factsShutterstock

84. Well, That Came Out Wrong...

I'm female. I wanted to try to flirt with the cute cop guarding my work building, so on my way back from walking in the rain without an umbrella, I tried to make small talk about the weather. What came out instead was: "In case you didn't know, it's raining outside. Just take a look at me, I'm nice and wet".

His face turned bright red and once I realized what just came out of my mouth I stuttered something like "no, no, I mean....uhhh". And then I ran up to my office and hid the rest of the day. Never saw him again.

Most Embarrassing Flirting Fails Factseazybnb

85. Take The Hint, Fella

Biggest fail of when someone was trying to flirt with me: I was leaving a party in college, a cute girl offered to drive me home, I said no because I lived one block away, she was persistent, so was I...

Took me a couple of days to figure that one out…

Most Embarrassing Flirting Fails Factsflickr

86. On The Rocks

During my senior year of high school, I had a girlfriend who I had been going out with for a while. With graduation getting closer and closer and each of us having different plans for our futures, things between us were starting to get tense and our relationship was feeling pretty rocky. After enduring this situation for a while, I decided to do something romantic to smooth things over again. What a mistake.

There were these really tall cliffs over the lake in the town we lived in. Our first official date was there, and in the early days of our relationship, we spent a lot of dates at those cliffs. When things got rocky, we hadn’t gone to them in a while. I thought that heading over there with her would be a great way to revitalize our relationship.

It was really still and there was fog over the lake. It’s a Great Lake, so it’s massive and it was unusual for there not to be at least some waves. We were sitting on the beach under the cliffs. She seemed happy and asked why I had wanted to come here. I explained my reasoning to her. I looked over to her and her face was in her hands. She said she wanted to break up.

So yeah, that was rough. But it’s been a few years, so now I can look back at it and laugh.

Jon Snow FactsMax Pixel

87. Talk About Bad Timing

Was hitting on this girl in college, was at a party we had going on in one of the halls (end of the term I think). Things going well, both having drinks and stuff, just as I’m starting to "make a move in" for a kiss this guy walks past with his girlfriend on his shoulders and the girl I’m flirting with goes "I wanna do that".

So, very drunken me picks her up, proceeds to walk her straight to the next hall, then I trip, she slips down and falls flat on her face, lots of blood pouring from her nose. I stand up to see her on the floor like this, and stupidly say "your face looks bad". Yeah, she never spoke to me again.

Most Embarrassing Flirting Fails FactsLittlest Pretty Things

88. At Least She’ll Always Remember You

When I was seven I had a crush on this girl in my class. I was the only boy in the class who actually liked girls by this age and I tried to hide it. At the same time though I really wanted her to be my girlfriend, whatever seven-year-old me thought that entailed. So I tried a bunch of different things, I invited her to my birthday party, where my brother made fun of me the whole night.

I always picked her when we played seven up, stuff like that. My favorite was when it was Valentine's Day and I wanted to impress her, so I tried to smell really good, I didn't own cologne because I was seven, so I covered myself in baby powder. No joke like head to toe underneath my clothes were covered in baby powder.

On top of that, I made this huge Valentine's Day card that had this picture of me and her holding hands I drew myself. When it came to hand out the Valentine's, we did, but I was so nervous when I did it, and everyone started mocking me saying I had a crush on this girl. It all became a little too much for me and I vomited... right onto my crush.

As if that weren't enough, upon realizing my mistake I blurted out "I'm so sorry, I love you!" as I was trying to clean the vomit off of her with my bare hands. Safe to say she didn't feel the same way.

Most Embarrassing Flirting Fails Factssimplemost

89. Prehistoric Mistake

Fancied a lass for ages. I was around 23, she was 22. We were heavily into raving/clubbing at the time, to Hard House specifically. Now, this girl Steph was really pretty but had a very unique bone structure to her face, the type models have. So I was pretty smashed one time when we crossed paths in a club and small talk ensued, so I basically said "Steph you are really hot and unique looking, you have the bone structure of a velociraptor".

She was genuinely horrified and we spoke very little after this.

Most Embarrassing Flirting Fails Factsfooji

90. Brace Yourself: This One Is Rough

I was like 11 on the monorail at Disney. There was a girl I thought was pretty but I couldn't think of anything to say. Right before she left for her stop I just said: "I like your braces". She looked at me like I had a third eye. My dad had a look of disappointment. It's a moment that still haunts me.

Most Embarrassing Flirting Fails FactsRegina Marco

91. Headlock Over Heels In Love

A friend tried to make himself look good in front of his crush by literally putting me in a random choke hold "for a laugh". It turns out it was because I was talking to her—I had a girlfriend at the time, we were just talking. It wasn't a chokehold though, it was basically just a headlock, so I decided to correct him. I was fairly oblivious and didn't realize this was a failed "alpha move".

It creeped the heck out of his crush that he would do that out of nowhere, and she stopped talking to him. Apparently, she quite liked him up until that point, so he kinda shot himself in the foot.

Tipping Point in Relationship factsShutterstock

92. The Seven Seas Of Regret

Stuck on a cruise ship for three days after my friend proposed to his girlfriend on the first freaking day and she said no. That same first night she made out with some random guy in the hot tub. I'm honestly not sure how devastated my friend actually was, but it was intensified by the fact that he'd drink himself stupid daily by 2 pm, which would lead to him going to beg her to get back with him.

At one point, she was sitting on the new guy’s lap at the bar and he grabbed her hand and "confessed his love for her" for what must have been the fifth time in two days. It was a constant battle of trying to pull him away and convince him to either go to sleep or come with us to another part of the ship. He is a good friend, so I felt terrible for him, ‘cause that was super awful on her part and tried to help him all he would allow, but it was awful to watch.

By the end of the cruise, the entire boat it seemed like knew what had happened. When I tried to bring it up with my girlfriend (who was on the cruise with me as well) days after we got home, she straight up refused to talk about it, saying that was painful enough at the time so we never need to speak of it.

Thomas Seymour factsShutterstock

93. No Me Gusta

In terms of real life, a buddy of mine was talking to this girl we all knew, and they'd been getting pretty flirty. So, the decision was made to invite her camping with us in the hopes one of them would make a move. Flash forward to that night and our buddy did seemingly everything he could to screw it up—spilled beer on her, stuck his finger in her mouth for no reason while she had a look of what the heck is going on here.

Finally, somehow, she still didn't hate him and toward the end of the night, he tried to kiss her and headbutted her pretty dang hard because he moved in too fast. After this, they had a talk because this girl was apparently the crown princess of second chances, and he threw up on her. Obviously, this was God's way of intervening.

Nicest Compliment FactsShutterstock

94. Musical Urinals

We went to a movie. During the movie, she got up to go to the bathroom. After she left, I thought I could run to the bathroom myself, and be back before her (for some reason, I thought it would be rude to leave her alone). When I came back to our seats, she was already there but I didn't give it much thought.

I hung out at her place for a bit afterward, gave her a kiss goodnight, and went home thinking that I just had a pretty nice date. A week later, after she wouldn't return any of my calls, I asked our mutual friend who introduced us what the deal was. Turns out that when I went to the bathroom, I accidentally walked into the women's room.

I peed in the stall next to her, and she recognized the boots I was wearing. She was totally freaked out. When I finally got a hold of her and tried to explain myself, she told me she was moving to Turkey to get back together with her ex-boyfriend.

Worst Thing Done on a Date FactsMax Pixel

95. It’s Just Not His Day

This romantic gesture was not done by me, but by my boyfriend. At first, I hated it, but it eventually really grew on me. It all started when, seven years ago, he promised me a mini-weekend getaway for just the two of us. We were going to have a romantic picnic at a secluded beach and then take in an intimate view of the sunset.

I’d say literally every single aspect of the plan backfired. First, he came to pick me up about two hours late. Later, I found out that he had been really busy preparing everything for the picnic. We drove there but, luckily for us, a fourth grade class field trip arrived at the exact same time. We quickly tried to find a place somewhere else. When we found a spot, my boyfriend told me to go ahead alone.

I then looked back and saw him pulling an enormous cooler, barely budging because of the heavy load. When I hurried over to him to try and help, the cooler tipped over and all the ice and contents fell onto the sand. He quickly started shoving everything back inside, cursing under his breath and saying sorry over and over again. The section of beach we found turned out to be dirty. The water looked like sludge and there was graffiti all over the rocks behind us.

The drinks and fruits were covered in sand and the sandwiches had water in them from the cooler. We later realized there was sewage in the water, which was why there was a horrible smell and a disturbing amount of flies around us. Needless to say, we didn't stick around till sundown. He didn't have money to buy anything else because he had spent it all on ice and drinks.

I paid for our Burger King meals. I hated this whole experience and thought it was literally the worst date that I had ever been on. However, later that evening I went home and realized how hard he had tried to make my first "real" summer date special. Despite everything that went wrong, that really meant a lot to me and I decided to give him another chance.

Seven years later, we're still going strong!

Romantic Backfired FactsPiqsels

96. A Family Affair

When I was 14, I was at a family friend’s Bar Mitzvah and I didn't know anyone. So, I was sitting there alone and then I saw this cute girl in the corner. I went over to talk to her and then we ended up just walking around this hotel and making out for about an hour (at 14, that was a big deal). Then she went off to do something.

About 15 minutes later I was sitting alone again when my mom called me over and said, "I didn't know she would be here, but this is my cousin and this is her daughter". I look at the girl and realize that my second cousin is the girl I had just made out with. A moment of horror as we look at each other and shake hands. She still hasn't made eye contact with me since then.

Nicest Compliment FactsShutterstock

97. Taking The Fall

So, I work in a workshop, and we often engrave stuff for customers. This particular guy wanted a nice wooden jewelry box for their wedding anniversary with a custom message he emailed me. For some reason, he chose to give the box to his wife at the workshop. Not the most romantic place I can think of, but whatever.

The guy's wife starts to look confused and tear up: "You don't remember the date?" Guy turns pale, looks at me with a deep stare, says: "No, I'm sure it's a mistake". Me: "No, I've copied it straight, can't be wrooon...waaait a minute, oh my god, it's my fault, I'm so sorry, I will redo it right away, no need to pay, please accept it as a gift."..

Wife gets angry a bit at me, but they leave with a different box and the correct date. But that wasn't even the best part. Guy comes back next day and pays triple the original price without a word.

Worst Mistakes Factsdavidkingraj

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