These Awkward Dates Are Painful

November 24, 2022 | Chelsea Gallagher

These Awkward Dates Are Painful

Human interaction is hard for everyone, but these are the cream of the cringey-crop. If you’re alone at home tonight, take comfort in these hilarious and embarrassing date stories. Grab the Ben & Jerry’s and read about others attempting, and failing, to find their perfect match.

1. Blinded By The Dawn

In my second year of college, I was pulling an all-nighter at the same time as one of my friends, who was very cute. We weren't in the same place, but we kept messaging over Facebook. It was really nice just talking with her. I had been single for about two months and was feeling confident. When dawn hit and our papers were done, she asked me out for celebratory breakfast.

I looked like I had just finished an all-nighter, and she looked radiant. As our breakfast went on, we talked, laughed, and the caffeine begins to mix with the satisfaction of completing my work for the semester. I’m feeling like I'm in a really good place. The sun is starting to fill the windows of the restaurant we're in, and there's this warm light everywhere.

She smiles coyly and asks me if I'm over my ex. I smile, say I am and I'm already thinking about who I'd like to ask out next. She smiles even broader and asks me who that is while touching me on the hand. And I said the stupidest thing possible. "Her name is Rebecca and she was in one of my history classes." Distinctly, this was not the girl I was out to breakfast with.

She looked devastated. At the time, I had no idea why. Realizing the mood had changed I quickly said, "I'm sad the semester's ending soon, but I'll see you in the spring!" I ran back to my dorm, ending what I would later learn was the first date with my future wife.

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2. Times Were Tough In The Nineties

My wife was set up on a blind date by a friend several years before I met her. They agreed to meet at a mall and then go from there. This is the late nineties, before cell phones, so he tells her he'll be wearing blue jeans and a Megadeth t-shirt and she tells him her outfit so they can identify each other. She arrives at the mall and sits down to wait.

After thirty minutes there’s still no sign of him. She’s about to leave when a guy approaches her and asks if she's waiting for a date. It's him, but wearing a completely different outfit. Confused, she asks why he told her he'd be wearing something else. His response was absolutely insane. He just shrugged and says his mom didn’t do the laundry yet. Two strikes...

They still decide to grab some food. He tried to use an expired coupon and started an argument with the girl behind the counter. At the table, he asks my wife if she knows how to cook. What meals does she know how to cook? Can she make this or how does she make that etc. The conversation continues but now he adds, "Do you do it naked?" after everything.

For example, she likes to go rock climbing, “but do you do it naked?" Or, I like to grow my own vegetables, "but do you do it naked?" Needless to say, my wife decided to end the date early and leave. He asks if she can lend him bus fare since his mom won't be coming to get him for several hours. He was twenty-seven years old.


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3. Frosty Valentine

This was embarrassing at the moment, but it worked out. It was a second date, on Valentine's Day, so I decided to go all out. I bought her flowers, a musical card, and chocolates. I was aiming to impress her and couldn’t wait to surprise her after the date. It was freezing cold, and I didn't have anywhere to keep the presents except my car, which I thought would be fine.

We finish dinner and everything is going smooth until we get back to my car. The flowers had withered, but I thought, “That’s ok, I still have two more surprises!” I hand her the card and hear it go bbbzzzzzz as she opens it. I sighed and said, "Well... I hope the chocolates are okay." She started laughing and gave me our first kiss.

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4. Anxious Love

My first date with my now-husband. Two very anxious people with no dating experience. We decided to go to the library and use their wifi to watch Netflix in the backseat. As soon as we got to the library he got out of the car and threw up in the parking lot. I then admitted to him that I had done the same before he picked me up. He tried to play it off, but we both knew it was nerves.

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5. Do You Have Chemistry?

We chose a late-night movie that ended around 2 am. Public transit had stopped running and we didn't have a car, so we walked back to her house. Exhausted from the walk, we collapsed fully clothed on her bed and fell asleep. Three hours later her dad shakes me awake. He finds out I’m studying chemistry but only has questions on thermodynamics...really not my strongest subject.

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6. Showtimes of Sadness

Back in middle school, my mom drove me to meet a girl at an outdoor mall to see a movie. It was an hour away and my date canceled on me fifteen minutes before. I felt so bad for my mom driving me all the way there that I pretended everything was fine. My mom dropped me off, and I watched a movie by myself. Almost cried but I kept it together.

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7. Number Two Secret

Second date but the first time at his apartment. After a few hours, disaster struck. Normally I’d never go number two at someone’s apartment but it was an emergency. The toilet wouldn’t flush and I ended up wrapping it up in toilet paper and hiding it in my purse! I slept over and the next morning the entire apartment stunk. He never found out thankfully and blamed his roommate for the smell.

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8. Drips Of Love

I met a girl through mutual friends, and we drifted in and out of each other’s lives for a few years. I finally asked her out, and we had a romantic dinner at an outdoor cafe. It was a beautiful late summer evening and everything was going really well. We head back to my place and start kissing on my bed when I feel something warm drip from my nose.

I was having a nose bleed and it was already dripping on her upper lip. I was horrified and tried to wipe it off my face, and hers, which just smeared it, and then ran to the bathroom for kleenex and a washcloth. She was polite but promptly informed me that she was leaving and wouldn’t let me walk her to her car.

As she walked out the front door, she turned and said, “It’s really too bad, because I was in a REALLY good mood tonight.” Then she was gone, and I headed to a bar to drown my sorrows. Somehow we’ve been together almost 10 years and married for six. Love you, sweetheart.

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9. Mom’s The Word

I was 13 and it was my first date. She wanted to meet and I asked my mom to drive me. Unbeknownst to me, after she dropped me off she stuck around to watch. My date and I began to walk when suddenly my mom yelled out from behind us. I was so embarrassed I wasn’t able to talk to the girl after and just went home very quickly.

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10. It Was You—Not Me

I was on a mediocre date, walking back to her apartment. On the way, she took a phone call about a couch she was buying. This call continued for the next few hours. She insisted I stay and put on Netflix while she was on the call. After she hung up she said, “There isn’t going to be a second date, is there?” I agreed there would not.

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11. On Thin Ice

I went on an ice skating date with a professional figure skater. I knew skating basics and could get from one side of the rink to the other without falling, and sometimes even stop without hitting the boards. By the end of the date, I had managed a few moves including a pirouette but also fell several times to the amusement of bystanders.

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12. Good Instincts

My date and I met in a park and were walking around getting to know each other. He suggested walking into the woods, and I said no because it was the first time I had met him. He was immediately offended that I didn’t trust him. It wasn't personal, just common sense on a first date. Against my better judgment, we continued to dinner. I should have listened to my gut.

The restaurant brought him the wrong food and he was very upset and angry about it. At the end of the meal, I wanted to split the bill and was so anxious to leave I had trouble with the math. By accident, I tipped more than I intended. He was again immediately offended. Never saw each other after that and I’m still cringing.

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13. Love Stinks

I wouldn’t call this a date, but it led to us dating later. We were friends at work and would go walking at this big park near the office. Afterward, we occasionally bought bottled water from Stop N Go. One night after a walk, the lot was full so I had to park at least 10 or so parking spaces from the front doors. On this particular night only I went in to buy water, and she waited in the car.

I buy the water and come out of the store and notice that she has both of the windows halfway down. It’s a chilly fall evening, and I remember the windows had been up when I got out of the car. So I get in and it reeks of horrendous gas. She’s frantically apologizing but I can’t stop laughing, and soon neither can she. That was the moment I knew we could be more than friends.

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14. Backseat To Love

The year was 1991 and I finally asked out a really gorgeous coworker. She says yes and I take her to a friend's party. Once we’re there she proceeds to get on the drinks and spend the evening flirting with another guy. The evening ends and she brings her new friend back in the car. They make out with each other for the duration of the drive.

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15. Main Course Mortification

When I was in high school I dated a guy with IBS and my parents insisted on having him over for dinners where he would just sit there because he couldn’t eat any of our food. It would’ve been fine if my parents ever let him and I cook, but even worse, we’re an introverted family. I still cringe thinking about the silence and him sitting next to me bored and hungry.


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16. Save Your Money Honey

Tale from my best friend and this guy she matched with on Tinder. He was running late so she texted him asking if he was cool with her ordering the pizza. He says yes, so she orders and pays for it. After the meal, he goes to pay and she tells him she already took care of it. He went off on her because he wouldn’t have eaten the food if he knew a woman had paid for it. Seriously.

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17. Equal Scoops

I went on a Tinder date with a guy for ice cream. We placed our order and when it was time to pay, the cashier asked if it would be together or separate. He berated her because men and women are equal and should therefore pay their own way and how dare she even ask! The whole store turned around to watch him yell at this poor girl.

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18. Just Desserts

I chose a dessert shop for a first date. Wanting to be a gentleman when the bill came, I told her, "No, it was great getting to know you. I got this." I tried to play it real cool—and ended up looking like an idiot. Walk up to pay with my debit card, and it's cash only. I don't have any cash and embarrassingly walked back to ask her if she did. I made it up with a second date on my dime, but we ended up not being compatible.

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19. Apologies From All Of Us

My sister-in-law set me up with a friend of a friend of hers. First impression, I’m relieved she looks like her picture, but then we start talking. She had a Korean boyfriend who had cheated on her. I’m also Korean, and she kept insulting Korean guys as I sat there listening. After her rant, she goes: "You're Korean right?"

I try to steer the conversation to other topics, but it goes back to her ex and her bashing all Korean men. Feeling uncomfortable I apologized on behalf of Korean men, and then made a hasty exit. She texted me as I was driving away that her next date showed up early. I wished her the best of luck, and immediately called my sister-in-law to complain!

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20. The Last Laugh

I had a date with a girl who asked me out. At the time, this had never happened before, and I was excited. We went for dinner and then picked a bar for a couple of drinks. We went back to my house and she politely informed me that we could chill at my house, but that she doesn’t sleep with people on the first date. "No worries," I told her and we hung out with my roommates and listened to music.

After a couple of hours, she told me she had a great time but that she was going to head home. Since my roommates were home she asked if I would walk her to her car. Once we got out there she leaned in and kissed me. I kissed back and a light makeout session occurred for maybe thirty seconds. We hug and she must have felt my bulge of excitement because she looked down.

I also looked down, and what do I see? My package visibly out of the top of my waistline. She loses it as if it’s the funniest thing she's ever seen. I stammered out an apology as she gets in her car. She never stopped heaving with laughter but said, “I’ll text you.” The joke ended up being on me because I dated that girl for a couple of months until she dumped me on my birthday.

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21. Falling In The Rain

In my freshman year of college, I went on a first date with a guy from my Italian class. We had dinner and were walking around when it started to drizzle. I was wearing ballerina flats with no grip. I took one step on the wet cobblestones and my foot shot out from under me. I landed on my back, hard. Mortified, I stood up quickly.

He asked if I was okay, and I remember saying I felt queasy. The next thing I knew I’m regaining consciousness in the gutter. I eventually got up and finished our date at the student health center. Turns out I'd broken my tailbone. I had to sit on a donut cushion in class for the next two weeks. Unfortunately, there was no amore.


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22. Don’t Judge A Girl By Her Nando’s

I took a girl out to Nando's once and she was really nice but a bit strange. We ordered and I’m eating mine, but notice she hasn’t touched her chicken. I ask if everything is ok, and she says she’s not hungry and proceeds to dump her entire meal into her purse. I’m shocked and a bit annoyed but everyone has quirks. I drove her home in silence, but my car smelled like Nandos the whole way.

She messaged me two days later saying she was really sorry for acting weird. A few nights prior to the date she had been at the Manchester Arena attacks and was extremely traumatized. We hadn't talked a lot before the date, and I didn’t even know she had gone. I felt really bad for not asking about it, but we never spoke again after that.

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23. Dial It Back

Technically, there was never actually a date. Back in high school, I called a young lady to ask her out only to be told she had a boyfriend and was away on a weekend ski trip. I learned this from her mother, who demanded to know who I was and why I was calling her daughter. I had looked the number up in a phone book and cold-called her house.

It legitimately never occurred to me that anyone else would have the brilliant idea to ask her out. I got off the phone and regretted everything. When I saw her in school the following week, I tried to apologize by giving her a rose. She freaked out and loudly recounted her mom's version of it, to everyone in earshot.

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24. Pointer Sisters

I was dating a ballet instructor and she had mentioned our date to her class. She taught teenage girls and there was a group of ten watching us when I picked her up from class. As we were walking to the restaurant/bar we noticed six of them tagged along and were trying to hide any time we looked in their direction. I thought it was funny at first—but it just got worse and worse.

We figured they would get bored while we had dinner but for the next few hours I’d catch them spying on us from different locations. It was like being followed by a bunch of little sisters. When we left and went for drinks, we noticed the youngest girls left but the older ones still followed us to the next place.

The entire night I thought we finally lost them, and I’d lean in for a kiss but catch one of them peeking in on us. We had planned on going to her place and even made a plan to split up and go in different directions but didn't want to reward their persistence with something juicy to talk about so we called it a night.

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25. I Don’t Like Coffee

I went out on a date with a girl going to college in a neighboring town. Dinner went great, and when I drove her back to her apartment, we sat and chatted in my truck for a few minutes. Then she said, “My roommates are out, do you want to come up for coffee?” My response was, “No, I don’t like coffee.” She gave me a strange look and we said our goodbyes. I was halfway home before it hit me.

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26. Behind Door Number One

My first date was when I was twelve years old and living in Germany. I took the bus to the air force base she lived on, and I was going to be early. Walking to her house I realized I didn’t remember the apartment number, and all the buildings looked exactly the same. I said hello to a lot of confused people that night after knocking on their door.

By the time I found her, I was really late and she was upset. We went to a dance where the boys I knew made terrible fun of me for having a date, and her friends were also being completely terrible. The night ended with her crying and me wanting to crawl into a hole forever. Petra, if you are out there somewhere, I am sorry.

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27. Date Duck Goose

On my first date with this girl, we went to a restaurant called "Duck Duck Goose" that promised duck and goose-based tapas-style dishes. We ordered duck meatballs and duck poutine. The duck meatballs had a sauce that just tasted like duck grease. After eating just one of the three meatballs she confided in me that she hates duck, and then I also realized, I hate duck too.

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28. All Good Dogs Get A Second Date

A woman asked me on a date to a dog park bar. I told her my dogs don't travel well so it would just be me. I arrived and she also didn't bring her dog and tells me she's a recovering alcoholic. So we're at a dog park bar with no dogs and no drinking. The date only lasted twenty minutes before she began crying about how she'd ruined everything and ran to her car.

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29. A Popeyes Reality

I had just got back from this long trip biking across America. One of my friends decided she had a crush on me after this. I was clueless to her new emotions, as we had always had a flirtatious friendship. When she asked if we could go out to eat I thought nothing of it. I chose my neighborhood Popeyes. She picks me up, full hair and makeup, I’m still oblivious.

When we got to Popeyes the cashier asked if we were dating. She looked at me and I said we were just friends. The rest of the time was really fun and we talked about life and my trip. She drove me home and we stayed friends for a few years. The embarrassing part for me is I didn't realize this was a date until a year later.

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30. A Repeat Performance

I met a woman online, we chatted off and on for a few weeks, and finally decided we should grab a drink. Things are going smoothly, and then she says that she’s happy I wanted to see her again. Confused, I asked her what she meant? Turns out we had met six months ago and I ghosted after. I didn't even recognize her or remember we went out.

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31. Best Friend & Worse Date

My best friend at the time was dating a boy who refused to hang out without his best friend. Their lack of independence resulted in me getting dragged into the worst double date of my life. We’ll call the boyfriend’s best friend “X.” He tried to make it less awkward by asking me out himself, while we were already on the date, to which I said no.

X spent the rest of the time aggressively yelling at me. Exclaiming, “I can’t believe you said no!” and “I can’t believe you don’t want to date me!” While we were watching a movie, in a public theatre. I had driven with my friend so I couldn’t leave. The plus side is his behavior was so bad I never got asked to double date with my best friend again!

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32. Rain On Me

I was on a first date with a girl and it was going really well. We'd only met the day before but we were vibing and I was feeling confident and optimistic. We were sitting near the front of the bar when she asked if I could pass the water. With my surge of confidence, I decided it would be funny to hold it over her head.

I thought it was even funnier to pretend to drop it on her head. Then my hand slipped, and I actually poured the whole jug of water on her head. In front of the whole bar. Pretty sure she understood it was an accident, but by that point, the damage was done, and there were several tables of people laughing at us.

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33. Rain Or Shine

My girlfriend and I planned a nice picnic/fishing daytime date. Everything was out on our blanket by the river when it started to rain. It wasn’t a small sprinkle, but instead was turning into a full storm. We were quickly trying to gather our belongings and get into the car. Once everything was in the trunk I slammed it shut.

The very instant I heard it click I remembered inside the tackle box were the car keys. The rain was only getting worse, and we had no keys or cell phones. The closest phone was about a mile away, in someone’s farmhouse. The only other keys were thirty miles away, in the possession of her dad. So we started walking that mile, and I’ll let you figure out the rest.

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34. Slowly But Shirley

One day one of my classmates asked me why Shirley was mad at me. I honestly had no idea who Shirley was. About a week later I met her in passing and my friend told me that's who was mad at me. Fast forward a couple of weeks later, I was asked by my classmate if I wanted to go on a blind date. I told him it better not be Shirley.

The evening came and I waited at a bar to meet my blind date for a drink, and it turned out to be Shirley. I wasn’t that attracted to her, but I was raised to be a gentleman so, we had a nice couple of drinks. At the end of the evening, she tried to kiss me but I graciously and respectfully said no. I never had a blind date ever again.

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35. Don’t Follow Me

During the first round of Covid lockdowns, I met someone for coffee but the coffee place was closed. We decided to go to my place instead since it’s near my apartment. She agreed to follow me. I was nervous and distracted and I pulled out of the coffee place into a lane where you can only turn right because of a median.

I had to go left and there's another way out of the parking lot that would have been better. However, I turned on the one way and found myself going against traffic. Got to the end of the street fine but of course, she didn't follow me. I waited at a cross street until I saw her car and she followed me to my place. When we got out of our cars she was still laughing at me.

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36. Smell Ya Later

Many years ago, I was talking to a girl on a voice chat line. We ended up wanting to meet in person, so I drove to her house. From my place, it took about 50 minutes, and then we went out to eat. Later in the evening, we decided to get a hotel room for some fun. She gets on the bed, pulls off her jeans, and my god I have never smelled anything worse.

I end up standing at the edge of the bed trying to explain to her why I don't want to get on the bed for what felt like five minutes. Then she asks, is it a smell issue? I could not have been happier to hear her say that, because now all I had to do was say yes. I told her this was not going to work out. I took her home and blocked her number.


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37. Fly Away While You Can

I fainted at the zoo on a first date in the butterfly room. I have always had an irrational phobia of moths but I love butterflies. I didn't realize a beautiful "butterfly" almost the size of my face was, in fact, a moth. The second he corrected me, everything went black and I was down. I should have known that the moth was just too big. It was almost the size of my face. We still dated for almost six months afterward.

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38. Save Water, Drink Prosecco

On the first date, we were having dinner at a nice Italian restaurant and he asked for a lemon slice with his Prosecco. In his defense, he thought he was ordering sparkling water, but the waitress gave him a weird look. Later he made a hand gesture and sent his drink flying across the table and onto the back of the patron at the next table.

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39. Read The Room

My date took me to a bookstore. At first, I thought it was sweet because I said how much I like to read. We find books by an author I like and he picks them up and tells me he’s buying them for me. I ask him not to but he heads to the cash register. I wait outside mortified, and when he brings me the books, he’s somehow surprised that I’m uncomfortable.

The rest of the date was supposed to be pizza at his house and a movie. I knew him through mutual friends so I thought I would be safe. On the couch, as I sat further away, he kept trying to snuggle closer. I’m getting more uncomfortable, and go to the bathroom to take a breath and think of an exit strategy. When I open the door, he’s standing in the hall.

He compliments my dress and asks me to twirl, which I hesitantly do. Then he says “hold on” and grabs and grabs scissors before going towards my legs. I’m freaking out and he doesn’t see why! Turns out he’s trying to trim a loose thread on my dress but went about it the wrong way. He was mad at me for not wanting a second date.

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40. Deceiving Appearances

I met a very attractive, tall, and muscular guy at an uneventful networking event in New York at the end of last year. He invited me over to his place and I was understandably excited. When we arrived at his place, I was surprised to discover that he lacked a lot of confidence and wanted me to take the lead. I was feeling generous and wanted to make the most of the evening.

As I was on my way out, I noticed his flatmates had people over and were having a quiet party. I decided to stay a little longer but started having a really bad panic attack. The whole night just spiraled into a complete nightmare. I left as quickly as I could and realized my car battery had run out. I had no money so I had to walk back to my place in freezing temperatures.

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41. Do Your Best

My date picked me up and took me to get frozen yogurt. When we got to the shop, he did that annoying thing when the passenger reached for the door handle, and the driver locked the door. This happened several times and he was cracking up. We went to watch a movie, and he told me the ending as it was starting. I got home and blocked his number.

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42. Budget Blues

This happened on my one-year anniversary date with my high school boyfriend. We decided to go to a nice restaurant, and before the date, he called to ask how much he should budget for dinner. I told him 80 dollars. Everything goes great until he asks for the bill. While looking at it, he quietly asks how much money I brought.

I didn’t realize he had also asked a friend how much money to bring and followed their advice instead of mine. He was 15 dollars short, and this was before the age of everyone having debit cards. We called my dad to explain what happened and ask for help with the promise of paying him back. Dad came to the rescue and told this story at our wedding.

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43. Try To Disconnect

My date was on her phone the entire meal as I was trying to talk to her. Just to test her I asked, "How's your steak?" To which she told me it was great. She was eating fish because she’s a vegetarian. At the end the waiter asks if we want the bill on one receipt or separate, I immediately said separate, cue her confusion.

She looked unhappy but didn't say she was upset. I said, "Look, I didn't come out here to date your phone. You've been pretty rude the whole time and ignoring me. Be glad I just didn't get up and leave, not like you would've noticed anyway.” All she could say was, “You asked me here, and I'm here with you. Why would I pay for this?"

I responded with, "I invited you and asked for your time. I wanted to go on a date, and get to know you. I didn't get your time, your phone did. I'm not paying for you to date your phone." Looking back, I could've been a bit nicer about it. That girl was not ready to date anyone for a while with that kind of addiction.

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44. Embarrassment Sunny Side Up

I had been chatting up this really awesome dude and he invited me over to hang out one night. At the time I didn't have a bank account and just kept cash on me. On my way there I ask if I can stop and pick up anything from the store, and he replies that drinks would be good. I ended up spending a fantastic night with him cuddling.

The next morning, I invited him to get breakfast with me. Breakfast is going great until the check comes. I grabbed my wallet to pay, and completely forgot I spent all my cash on drinks the night before. I wanted to fall through the floor. I’m apologizing while asking him to cover breakfast promising  I’ll pay him back that afternoon.

He explains he didn't bring his wallet because I said I wanted to treat him. He tells the cashier that he lives nearby and just needs to go home and grab his wallet. I had to be at work soon, but offered to drive him back. He assured me it was fine and he would just walk back. We were laughing, but I was mortified on the inside.

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45. Would You Do It For A Scooby Snack?

When I was working sales I completed an intricate order with a guy from the manufacturing side. Once it was done, he invited me out to dinner to celebrate. I had never met him before, but we had spoken so much through phone and email, I said sure. We ended up meeting at a chain restaurant. As soon as I saw him I knew the night would be awkward.

Honestly, he looked the way I expected...except that he was dressed head to toe in Scooby-Doo gear. A grown man was wearing matching Scooby clothes, including a hat. The minute we sat at our table, he started talking about Scooby-Doo. He asked me what my favorite episode was, my favorite character, and with whom do I identify the most.

This was over the top, and he did not talk about anything else, even when I changed the subject. I remember looking over at a table where another couple sat, holding hands and laughing with each other, and thinking "that must be nice" as he began telling me about his Scooby-Doo collectibles and their values. When my food arrived, I immediately asked for a box.

He went quiet, and I could tell he knew the date was done. We split the bill and as I walked out to my vehicle, he said, "We're not going out again, are we?" I told him no, we aren't, and he wished me well before walking away. I honestly felt bad for him. He knew what he was like but just couldn't help it. Nice guy, but I couldn’t cope. I hope he eventually found his Velma.

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46. Mumbles & Bumbles

On a Bumble date, he ended up talking about aliens making the world according to the book of Genesis and the earth being flat, very loudly in a coffee shop, with all of his proof. He sounded like the History Channel at 2 am. I tried to be as polite as possible but he was ridiculous. I am not sure if I was embarrassed more for me or for him.

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47. Katie, I Am So Sorry

This date happened when I was 18 and she traveled an hour to meet me after we matched on Tinder. We went to a cafe I had been to plenty of times before, and after we ordered I started talking about ketchup; EXCESSIVELY. I didn’t know what to talk about so I decided to bring up how I used to drink ketchup from McDonald’s when I was hungry.

Back then I had anxiety about using my debit card in public, and when I realized I had no cash; I started silently sobbing. She paid for me, and the woman serving us asked if I’d like to take my food to go. I looked at her, my eyes full of tears, and said, “Yes. I’ll take the rest of hers as well.” I didn’t ask her before I said this.

We walked out, and I immediately threw the food into the trash outside the front door. She asked why I did that and I told her it was an accident. The total date was an hour and a half and I’d managed to cry; talk about my weird childhood habits and make her pay for me. Without telling her, I walked her to the bus station and said, “I think you should go.”

Embarrassing datesUnsplash

48. Plenty Of Fish In The Sea

I was messaging with a woman on Plenty of Fish, and her pictures were a little blurry. We messaged back and forth a few times and she offered to send me some more pictures in my email. She was cute, not gorgeous, but with curves in all the right places. I appreciated that she asked me to meet up and I figured why not!

She chose a particular restaurant for dinner. I got there a little early, and she showed up a few minutes after I did. I couldn't believe what she was wearing. I could only describe it as a prom dress. She explained that she doesn't go out very often and likes to dress up when she does. She was also wearing some very high heels, and definitely not comfortable.

We go into the restaurant and sit down to order a drink when a couple of her friends "just happen to show up” and come over. Comments like, "Is this your date? Oh, y'all are going to have so much fun tonight, do you have any cute friends you can hook us up with tonight? What are y'all doing after dinner?" It was all too much for me.

We ate and I told her I appreciated her meeting me for dinner but I didn't feel like we were hitting it off. Undeterred, she asked if she could come by my place, for a one-time kind of thing. I gently said no, and she started crying. I jumped in my vehicle and put the pedal to the metal. I haven't been back to that restaurant since.

Embarrassing datesPexels

49. Patiently Waiting

Over 25 years ago a coworker set me up on a blind date. The evening arrived, and I was a little early at the restaurant. Feeling anxious, I ordered a drink, and chatted with the waitress, telling her I was on a blind date. After the first drink, I checked the time and my date was 15 minutes late. City traffic. I figured. But the seed of doubt was planted.

I finished the second drink quickly while battling new anxiety mixed with doubt, and a bit of fear. I took a deep breath, sighed, and tried to relax. "Still waiting?" the waitress asked, startling me out of my worry. I tried to laugh, but it felt hollow. Checking the time again, my date is now 45 minutes late. I felt terrible—but I didn't know this chilling truth.

My face was red and I wanted to shrink into the booth. At the hour mark I couldn't take it anymore and gave up. As I was paying, my waitress found me. "She stood you up," and I just nodded. Then I walked out the door and went home. I found out two days later, my date had passed in an auto accident on the way to the restaurant.

Embarrassing datesPexels

50. The Last Laugh

Went on a date with this girl a couple of years ago to a comedy show. I picked her up and she was a little tipsy from day drinking with her friends. We go to the comedy show and get seated in the first row. I don’t recall who the comedian was but he did a lot of crowd work. Halfway through, I look over at my date, and she is head back, mouth open passed out. I knew what was coming—but it was still brutal.

The comedian begins ripping into me about boring my date to sleep for five minutes. By this point, my date wakes up and is with it for a minute or two, but then falls asleep again!  By this point I could tell the comedian would not let me live this down and everyone around me was laughing and giving her concerned looks.

The waitress comes over and pulls my date to the side, giving me an excuse to get my date away from me (good on her for looking out), and asks her if she was safe. Thankfully we were new in our short relationship because she told me after that if we were closer she would have pranked me or something. Didn’t follow up on another date.

Embarrassing datesPexels

51. The City Of Dates

I had just moved to San Francisco from college and started talking to this guy on Tinder who was in his late 30s/early 40s. I hadn’t had much luck with older dates previously but I decided to be more open-minded. We got cocktails and on the date, I acted as pleasant and engaged as I could even though there was not much chemistry.

After one drink we decided to part ways, and he offered me a ride home. Once I got home, I received a message that was paragraphs long from him! He really wanted to leave the whole time but stayed to pay for my drink and give me a ride home. He also let me know I was overweight, unattractive and I had acne that was disgusting.

My heart sank after this unprompted and completely unnecessary message. I immediately deleted it and blocked him but the words still replayed in my head. Even now I still think about it, and it makes me sad that I dimmed my light because some guy decided to be awful.

Embarrassing datePexels

Sources: , ,

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