Dating can be difficult. Getting through the first date is often the hardest, and these people found that out the hard way. Keep reading to discover what horrors befell these poor souls just looking for love. Shockingly, they didn’t give up dating altogether!
1. You’ve Got To Be Tripping Me
This chick hit me up off a personal ad, and we seemed to hit it off. She was a little older than I was, and the picture made her look a little bigger than I would normally go for...but whatever, she seemed cool.
It was a bit weird that she wanted to pick me up rather than meet somewhere, but whatever, things happen. I should've stopped everything when a dingy old Honda Civic rolled up, and someone who was not a little older but a LOT older and a LOT heavier than I expected got out.
But I didn’t—and I had no idea I was in for quite a night.
I didn’t want to offend her by doing the 180 back into my house when it was abundantly obvious that her picture was really out of date. So, I got into the car, which was full of trash, and we set out. She told me she needed to swing by her place, and I said sure.
Her place was in the projects. She invited me inside, and I figured it was better than sitting in the car waiting to get victimized.
I joined her inside, where I met her boyfriend and kid, neither of whom she'd thought to mention before. Her boyfriend was remarkably laid back about me wandering in, apparently on a date with his girlfriend, and promptly offered me some of whatever he was having.
I declined, mainly because even with my experience, I couldn't identify the mounds of colorful pills and other paraphernalia he had.
Her kid, meanwhile, was toddling around oblivious while my date did whatever it was she was doing in the bathroom. We wound up watching The Simpsons like some weird extended family.
Then things really got interesting. The boyfriend didn't know exactly what he'd combined and he started tripping, freaking out. I had to talk the guy down through a hallucinogenic experience. My date came out from the bathroom sometime later to find him on the floor without any clothes on.
She didn’t seem surprised by this at all, as if the whole evening was perfectly normal. She asked me if I was ready to go.
I asked if we should be concerned about leaving the guy there when he still had several hours to go and a kid around, but she shrugged and assured me everything would be fine, so we headed to the car.
She started driving, and we were discussing where to go for dinner. I knew a really nice restaurant, which she said was too fancy. I knew another restaurant, but she didn’t like their food.
I knew a quirky hole-in-the-wall that was kind of gross but had fantastic food, but she didn’t want to go that way. She suggested Taco Bell.
I made a noise that was somewhere between "uhm okay" and "really", which she took as agreement, and we went to Taco Bell.
At that point, I was just happy not to be in the projects, so I made the best of it, ordering a couple of tacos. Being the gentleman, I paid when she ordered what seemed to be half the menu. My chance came when she disappeared into the bathroom.
Without even thinking about it, I was gone. I was out the door and halfway down the block before I even realized what I was doing. I saw her in the distance, back at the Taco Bell, bursting out the door and looking around.
Then she started shouting for me to come back. I saw her get in the car, but she wasn’t going home. She was starting to look for me.
This particular Taco Bell was on a main drag that backed up to a residential neighborhood. So, I wound up hiding behind hedges and shrubs as she patrolled the streets searching for me.
This went on for two or three hours, with me skulking in the bushes as she circled the block and drove up and down the streets. I managed to work my way back to my building, only to find her waiting in her car out front.
However, she didn't know about the back entrance, so I snuck in that way and left all my lights off. I locked and barricaded the door. The sight of someone strange lurking in the parking lot at that late hour prompted one of the neighbors to call the authorities.
She refused to leave. She called the officers several interesting profanities, especially when they decided to take her in for disturbing the peace. She even took a swing at one of them. The next—and only—time I saw her again was when her picture appeared in the next day's newspaper.
2. An Evil Twin?
I met a girl at a friend’s party. We were both in our mid-20s. We ended up spending three hours talking, and she was funny, charming, gorgeous, and carefree. I asked her out and I got a wonderful “I would love to” from her.
I showed up about four days later at the restaurant she picked, one within walking distance of her place. She arrived about five minutes later.
“Nice place,” I said as I got her chair for her. “Since it’s so close, do you eat here often?”
She scowled and responded, “You know, you ask too many questions”. I was floored. Everything continued downhill from there. Within about 20 minutes, she just got up and left.
I felt as if she had failed to tell me that she had an evil twin, and that’s who showed up. Later, when I ran into my buddy, I asked what the heck was up. “Oh yeah,” he said, “She’s a piece of work until she gets a few drinks in her. Then she’s adorable”.
3. Salivating Over The Server
I took this girl to dinner, and she could not stop staring at our waiter. He was square-jawed and muscled, the college athlete type. I get it. But I didn't appreciate that she literally craned her neck every time the kitchen door swung open to see if he was walking out.
Eventually, I gave her enough cash to pay for my part of the meal and suggested to her that she should get his contact info when she paid the bill and left.
4. Back With Baby
I picked her up, and she asked me if we could stop by her mom's house so she could run in and grab something. I said sure and made the stop. She went inside. Five minutes later, I couldn't believe the scene that unfolded—she came out hustling towards the car with a car seat and her mom chasing after her, yelling.
She opened the car door, threw in the car seat—which now had a baby in it—and started yelling at me to drive. I freaked, turned my car off, and took the keys out of the ignition. Her mom called the authorities, and they came and questioned all of us for a good while.
It turned out she had lost custody and was trying to use me as a way to get her kid back. We never made it to dinner, and I just went home after the officers left.
5. Where Did BAE Come From?
I went to dinner with a girl whom I'd been crushing on for quite some time. It seemed to be going well, and we ended up back at her place. Out of nowhere, her boyfriend—of whom I was not aware—came back from out of town and stopped in unexpectedly.
He and I had a very awkward conversation for a few minutes, and then the two of them disappeared into another room for a minute or two.
She came back and said something to the effect of, "I don't have a place for you. I'm sorry". I just got in my car and drove home with one of the strangest feelings that I'd ever felt. At some point, a few minutes into the journey, I couldn't contain myself and I busted out laughing.
6. No Apologies, I Was Out!
The guy told me he would still be together with his kids’ mom if she had apologized for what she did wrong. Out of curiosity, I asked what she did. I was expecting something like she cheated or something that actually needed apologizing for, but no.
She kept nagging one day and wouldn't shut up, so he tied her to a computer chair, went out for three hours, and left her there. I said it didn’t sound like she was the one who needed to apologize, and I left.
7. This Date Went In A Bad Direction
I lived in NYC, and she lived in the suburbs. We decided on a small chain restaurant, and I said that the one close to City Hall was the best location for me. She agreed to meet me there.
I arrived at the restaurant early and waited until a few minutes after our meeting time, then gave her a call. She told me she had no idea where she was and needed directions.
In an era of smartphones, that was a puzzling thing to say, but I gamely tried to help. It was really hard to get her to look at the street signs for some reason, but once she did, it was clear she was in Midtown, several miles away and nowhere near City Hall.
I asked, “Didn’t we plan to meet at the one near City Hall?” She angrily answered that she didn’t know where City Hall was.
Again, how is that even possible with a smartphone, and why agree to go to a place if you have no idea where it is? She said she wanted to take a cab to where I was and asked me to pay for it.
I decided to agree to keep the peace since she was pretty much freaking out on the phone by that point. She arrived, I treated her to dinner, then I took her to a cool late-night teahouse, and we walked along the river.
I tried my best to make it a good experience, but all conversations fell flat. I finally asked her where she’d like me to walk her back to for the night. I was expecting to take her to a subway station because her suburb was quickly reachable by commuter train at all hours.
Nope, she needed me to walk her back to a parking garage back in Midtown, where she was when I’d called her at the start of the evening.
I’d had no idea she’d driven to the city; people usually don’t drive from her town because the train is so much easier and cheaper than paying for Manhattan parking.
Luckily, our nice walk along the river had gotten us halfway to the garage, so I offered to walk her the rest of the way, and she happily accepted. Here’s where it went from inexplicable to insane.
When we got to the parking garage, she asked me when our next date would be. Trying to be polite—instead of immediately replying “never,” I said we could figure that out over the next few days.
She immediately turned hostile and demanded to know why I wasn’t agreeing to a date right away. I replied I wanted to think a little before making more plans. She drove away, and I thought that was it.
The next day, around noon, she texted me, “You’re supposed to text ‘I had a nice time last night’ the morning after a date”. I replied, “I didn’t realize that was a rule”. She said, “It is. I can’t believe how rude you are.
You need to pay for my parking garage because you sent me to the wrong place”. I answered, “I don’t think so I paid for the taxi, but that’s all I’ll be doing.
“I didn’t know you were even driving, and I told you which restaurant we were going to. If you didn’t know where City Hall was, you could have asked for a specific address”.
She replied, “I am going to tell [employer] how you treat people,” to which I said, “…reasonably?” I then blocked her and am glad to say I never heard from her again.
8. Whipping It Out
He took “it” out. And I don't mean this in a funny "unexpected Seinfeld" kind of way. He leaned across the table and whispered, "I'm out". I said, "Excuse me?" For some reason, my first thought was, "Out of the closet".
He said, "Out, under the table. Look under the table".
Like an idiot, I LOOKED. His next words were even more horrifying. He then said, "That's what you do to me". I replied, "This is what you do to me," and left. I'm a people pleaser, so, to this day, I'm proud of myself for walking away in the middle of dinner.
9. Too Much Crazy For Me
I met this girl on the app, and we were talking. She invited me over hours after matching. Her mom was there and was completely trashed. She was at the table just mumbling, dozing off, and asking me crazy stuff.
Then, her sister and her BF were there, and they were also plastered, having a screaming match while we were all talking and hanging out at the table.
She seemed more normal than the other three, and most of the time, she was just talking about her daughter, how she lived in another state, and she's never had custody of her.
When I was leaving, she asked me about a second date, and I told her, "Sorry to be blunt, but that was a mess. I was very uncomfortable, and I don't think we'll align".
She went off on me saying, "Everyone has a crazy mom, it's normal," how "[trashed] people fight, it's what they do," and how I sounded like CPS.
She started hurling insults at me and then said I should've disclosed my "medical condition". I had no clue what she was talking about.
Krakenimages.com, Shutterstock
10. Right Career, Wrong Date
While on a date, I was asked when I would get a real career. I love what I do. I'm a union stagehand in a major entertainment city. I have been in my industry for over 20 years, toured the country, toured the world, and made a comfortable living.
Yeah, no. That was pretty demeaning, and I was out.
11. Under A Cloud Of Suspicion
I was newly out, and I had had a crush on her for ages. So, when she asked me out, I was very excited. She was pretty, smart, very laid back, and had a great sense of humor, so things were going great initially.
The end of the date came around, and she very casually dropped on me that she was involved in an open investigation for vehicular manslaughter. She even hinted that it was purposeful and did not seem regretful. That was the end of that.
12. Her Man Stash
She kept talking about the "emergency guy” she had stashed around the city. She was like, "I've been really busy with [grad] school, but I don't go without. I have plenty of emergency [dudes] around town". That was bad enough—but she just kept making it worse.
And when I say she kept going on, I mean she KEPT GOING ON. She was telling me about the two guys downtown, three in the suburbs, one near campus, and two in her apartment complex.
It honestly sounded like I was new to town, and she was giving me a rundown of all the best places to visit. It was just weird.
Volodymyr TVERDOKHLIB, Shutterstock
13. My Spidey Sense Kept Me Safe
Nothing obvious or overt, but from the minute we sat down to eat, the hair on the back of my neck stood up and I felt unsafe. He was polite, listened, and was very polished, but I just could not shake that feeling. I drove to the restaurant to meet him, so he did not know where I lived.
After dinner, he asked for another date, and I just said, “No, I don’t think we are a good match”. I gave him money to pay for my half, said goodbye, and when I got to the door, he was staring at me with an expression I never hope to see again.
I ran to my car, moved it to another spot, and waited until he left before I did so he could not follow me.
The restaurant was on an isolated road, so that was safer than having him catch up to me. I found out about a year later he was put away for accosting two different women. It happened on the first date. I never used a dating site again.
14. Saved From A Drive-In Disaster
It was my first date. I was 17, working as an office assistant's helper. The guy, who was 20, also worked there. He asked me to the drive-in movies.
He came to my house, met my mom, and did the whole song and dance to her about taking good care of me, getting me home on time, etc. I was still nervous, so I arranged with two friends to go to the same movie in their car; my date didn't know.
They parked three cars down from us. After we parked, the guy told me to relax, he just wanted company for the movie, and he respected me. The movie started.
I don't think the opening credits had finished and he was all over me. It was like he grew four extra arms in seconds! I pushed him off me.
He apologized and said he was sorry. He thought I'd like it and he couldn't help himself because I was so cute. I told him I didn't like it and to keep his hands to himself. I got about two drinks of my soda down, and he tried again.
Now I was mad. I got out of the car, threw my drink at him, and walked off.
I went to my friend’s car and got in. The guy didn't see where I went because he was dealing with dripping soda on him and his car. My friends and I left. The following Monday at work was really awkward, and he avoided me like the plague.
I've never again dated anyone I worked with.
15. Multiple Reasons To Dip
She wouldn't stop going on and on about how much she wanted a baby. She called it "her little creation" and how she wanted multiple.
She tried to convince me to come back to her place for some fun, but I dropped her off and dipped right away. She texted me every now and then after trying to meet up again. No way.
16. The Date Stunk, And So Did She
She looked nothing like her photos and smelled of cat pee-covered taquitos. We were at a park and saw some girls playing softball. That's when her true colors really came out. "Those girls look special ed with those helmets", she said.
I'm always down to give someone a chance, but just yikes. I made an excuse to leave. My car smelled for two days after that.
17. A Cackling Cretin
We went to her place to watch movies, and we chose Kung Fu Panda 2. From the moment it began, she proceeded to cackle at every single joke. Anything that could even be perceived as mildly funny set her off, like The Wicked Witch of The West.
I know some people have interesting laughs, and that wouldn't be so bad if it wasn't constant from beginning to end.
After that, she put on Iron Man, and the same thing—she cackled the entire movie. There's a point in the movie where a character’s phone goes off, and the ringtone is an old Iron Man theme, which made me chuckle.
She turned to me and said, "You laugh at all the weirdest parts!" The second the movie was over, I got out of there and did not see her again.
OWL_VISION_STUDIO, Shutterstock
18. He Didn’t Make The Cut
The date felt more like a job interview to fill a position rather than an actual date. He gave off the vibe of someone who wasn't into getting to know me as a person but just listed his wants and needs. So, at the end of the date, he asked how I thought it went, and I said I didn't feel a match.
He said he was missing the “wow factor”. I laughed, slightly offended. I had no idea I was auditioning for a contest. I was happy we only went for drinks, but even that felt a bit too long.
19. I Couldn’t Get Past The Future
One time I went on a date with a girl, and during the date, she started talking about future plans with me. She was talking about how we were going to have kids together and how we were going to go on trips with my brother and his wife.
I was in my mid-20s and had just started my career when this happened, so of course it freaked me out.
Who jumps to those kinds of conclusions during the first date? It was super awkward because she worked with my mom and kept asking about me.
20. Done Over His Disposition
He threw a temper tantrum that I couldn't overlook. The reason why was ridiculous—it was all because the restaurant he wanted to go to was closed due to the tropical storm that was going on. It was sad because I was having a great time walking around Manhattan while the storm raged.
I had every intention of going home with him, until the tantrum.
21. Wasting Away In Margaritaville
She showed up plastered to a casual daytime first date at a bar I frequented. She proceeded to order a premium skinny rocks margarita and downed it.
Then ordered a second one. The conversation was all over the place, and I was pretty much done. I went to the bathroom, came back, and she had another margarita being served.
She went to the bathroom after that and the bartender, who I was pretty cool with, flat out asked me, “Bro, is she your date? When she ordered the third one, I said she needed to slow down.
She told me it’s OK, you were paying, and you’d drive her home”. I told him I was going to bounce, and if she doesn’t pay her tab, text me and let me know so I can pay it later.
He was cool with that. So, I left. She did pay her tab. She randomly texted me a few days later and asked if I was doing OK. I did not respond.
22. Something Seemed Familiar
The date was going great, but we were talking about family and friends, and I realized that I’d slept with her sister.
I didn’t really know what to do, but you can’t just say, “Oh, your family looks fun, and I slept with your sister not too long ago. Show me more pics of your dog; is she a lab mix?”
I cut the date short after dinner and hoped it would just fizzle out, but they found out. It was cool, though, just an awkward coincidence.
23. Desperate For Love
He was clearly desperate to put a ring on ANYONE'S finger. He was intensely, overly romantic despite not knowing me really at all. The date was on a Sunday, and he put on Etta James' “Sunday Kind of Love”.
He tried to sing it to me while looking excessively earnestly into my eyes. He was also in the service, and we were both like 19. Go figure.
24. Out With The Old
He was making suggestions for what he thought we should be doing right there in the restaurant. They were extremely inappropriate—and he went too far.
So much so, the random couple sitting at the next table over asked me if I needed a safe ride home during one of the numerous times, he left the dining room. It was New Year’s Eve. I was home by 9 PM.
25. She Had Some Great Expectations
While we were having lunch, we ran into a friend of hers I didn't know, and he stopped to say hi. Their brief conversation somehow brought up that she owed the guy a meal because he'd paid for their last lunch together.
So, she offered to pay for his lunch to square it away and he agreed. He ordered something to go and told the waitress she'd pay for it.
They both said their goodbyes, and the guy left us alone to go wait for his lunch at some other table. So far so good. Their conversation was a bit strange, but it seemed like it came up organically, didn't needlessly drag on, and the guy was nice at all times.
He was also polite enough to make himself scarce as soon as possible instead of inserting himself into our lunch date.
So, we continued our conversation, and everything seemed fine, until sometime later after the friend had already left and it was time to settle our check.
I realized this girl obviously expected me to pay for the whole thing—including the lunch she offered to pay for her friend as a way to pay him back for the favor he did.
Even if the friend hadn't ordered a pretty pricey meal, it didn't sit well with me how she had shamelessly decided to pay him back with my money in what seemed like a deliberate sham.
So, I paid for the whole thing in order to avoid making a scene, but later brought it up and told her that it wasn't cool.
She made it clear that she saw nothing wrong with it and said I was being cheap and childish. I thanked her for her honesty and told her we were done, and I wasn't going to be calling her again. She tried to argue that I was overreacting, but I held firm.
I blocked her a couple of days later because she kept texting me to convince me that I was wrong and that we should go out again. Some people really live in an alternate dimension.
26. An Ex-tremely Bad Entanglement
I matched with a girl on Tinder, and we decided on drinks downtown and a walk around a popular park to chat. She messaged me at the last minute to meet her at her place instead of the restaurant that was three minutes from my subway stop.
Fine. I had to get off the subway and walk 20 minutes in the opposite direction of the restaurant, but I'm a nice guy, so whatever.
I showed up at her place and she invited me in as she needed to finish getting ready. I sat on the edge of her bed as she got ready, and all I could hear was people getting busy through the wall. She told me it was her roommate and her new boyfriend like it was totally casual.
She then asked me if I wanted to "compete" with them to make her roommate jealous.
I politely said no because I was starving and wanted to go eat. I didn't tell her I wasn't expecting any action and didn't have protection. We walked to the restaurant, and she proceeded to talk about all her exes and how they ruined the relationship.
Whatever, I can deal with it. Who hasn't complained about an ex?
Dinner actually went pretty well, mostly because I had a few drinks to relax, and it was a chill restaurant. After dinner, she said she was tired and asked if I could walk her home.
No problem. I already had a feeling this wasn't going anywhere, so I was excited to leave early. We got back to her place, and the roommate was in the kitchen getting drinks.
She straight up told her to stop getting busy with her ex so loudly in the next room while she was on a date. That's right, the roommate’s boyfriend was the ex of the girl I was on a date with.
The roommate then commented on how I was next, and they started a screaming match. I told her I was going outside so they could hash it out.
The second the door closed behind me, I basically jogged three blocks towards the subway to get out of there. I texted her when I got home and said I had fun getting to know her but was not interested as we didn't have much in common.
There was no response.
A week later, she sent me a racy photo and asked me to come over. I never thought I'd hear from her again, so I blocked her, and that was it. The worst part was the restaurant was a sick Mexican place that she said she frequented, so I never went back out of fear of running into her again.
27. Gone In The Flick Of A Twitch
I went on a date with a man whom I'd previously met on a night out. He seemed nice, so I was looking forward to the evening. We went for a meal first, and as we were talking, I kept noticing he kept doing this weird shoulder twitch.
I don't know if he was even aware he was doing it, but it quickly started to be annoying, as I couldn't keep my eyes off his shoulder.
He then started telling me a story of how he used to be in the Army and how his wife, who was also in the Army, had been ended. They had a child together, and he had raised her on his own.
This was a horrific story, and I sat in stunned silence as I just didn't know what to say other than I was sorry that had happened. After the meal, we went to have a drink in a pub across from the restaurant.
He immediately picked out a bloke in a red top and started saying he shouldn't be around here because it wasn't his territory. He then pulled a knuckle duster out of his pocket and put it on his hand while staring at this guy who was just having fun with his friends and hadn't once looked over.
The red flags were literally smacking me in the face, so I made some excuses and left. I only dared tell him by text that I didn't want another date.
Nicoleta Ionescu, Shutterstock
28. A Victim Of Voice Fishing
Years ago, I went out on a date with a guy who voice-fished me—like catfished me with his voice. He had already sent me a video that he was talking in, but when I met him, he sounded completely different, with a slight lisp.
I would have gotten over that, except for one major red flag—he ended up taking me to a gas station to talk to his friend at the pump for 45 minutes. I faked an emergency and went home. I have had much worse first dates than that, but that one left me flabbergasted.
29. Nothing’ Happening ‘Round Here
I met a guy on a Counting Crows online forum, and he happened to live a half hour away. I thought, “Cool, let’s grab drinks at [local bar] and see where it goes”. I got there, couldn’t find him anywhere, and figured I had been stood up. Then, the lights dimmed.
He walked out on stage, completely plastered, garbling every other word, and proceeded to play “Round Here”. He stopped halfway through to vomit on himself. Now, I can never hear that song without cracking up.
30. Act Your Age!
She ordered a $100+ steak and lobster meal and got trashed. I had to pay for the whole thing because she didn't even bring her purse.
She almost made me crash while driving back to her place because she was frisky and put her leg across me and accidentally hit the steering wheel. Then, she threw up when we got to her place and told me to sleep on the couch (I wasn't expecting to stay the night at all).
I snuck out in the middle of the night and texted her, saying thanks but no thanks. She proceeded to insult and berate me, then switched to saying she was willing to work it out if I was, then switched back to insults again when I still said no thanks. She was 10 years older than me but acted like she was fresh out of high school.
31. Pipe Down Already!
I asked about his hobbies, and he said, "I play the bagpipes". I thought that was really cool and asked him to tell me more. He said, "Are you sure?" I said, "Yes". He then proceeded to go on about bagpipes for the rest of the night. How he felt playing the bagpipes was his calling in life, how he needed to carry his grandfather's legacy (who also played the bagpipes), how his dream was to play bagpipes for the queen, his favorite brand of bagpipes, the anatomy of bagpipes, etc.
Every topic was somehow turned back to bagpipes. To be fair, I did say yes to him telling me more. I hope he's doing well and found someone just as passionate about bagpipes.
32. Who’s The Old Lady?
I went on a first date to an upscale restaurant and bar. We met at the bar first for a drink to get to know each other, and then I was going to suggest moving over to the restaurant to get a table. It was a fairly large place with a large bar area.
During our “drink,” I noticed that she was always looking across the bar at this older lady, and the older lady was looking back.
It also appeared they were communicating with facial expressions. I wasn’t sure, but it seemed very odd to me. After our drink, we moved to a small booth in the restaurant area to get some dinner.
We were getting along great, but I kept noticing occasional odd facial expressions from her. The place had “mood lighting,” so it was kind of dark; I wasn’t sure. Eventually, everything came into the light—and I was mortified.
After we finished our appetizer, I excused myself to go to the bathroom, which was behind me. I noticed that the older lady from across the bar was sitting at a small table behind us. She was trying to hide but was not doing such a great job.
When I got back to the table, I asked her if she knew who the lady was and that I thought they were communicating.
She confessed that the lady was her mother and that she always brought her on first dates so she could give her an opinion and rate her date. So far, I was doing well, and her mother thought I was great.
I asked for the check, paid the tab—it included drinks and dinner for her mother—and cut my losses. On the way out, I told her to lose my number.
33. Puss-In-Woods
The dude talked about going to visit and petting his deceased cat in the woods. He became upset when I said that might not be the most hygienic thing to do and reciprocated by suggesting I don’t properly clean my jewelry.
I almost ran out of the restaurant. He even showed me pictures of the deceased cat.
34. Looking For Another Baby Daddy
This girl and I had an amazing time mini-golfing at the bar we went to. It wasn’t until the end that she casually mentioned she homeschooled her four kids, three of whom had different dads.
I'm all for living your life how you see fit, but I didn't want to be the fourth father to the fifth kid, and she really should've mentioned that in the messaging leading up to our date. I didn’t want kids, so that wasn’t a good match for me.
35. I Cast Out That Demon
This was back before the term “catfishing” was a thing. Lilly was supposed to be a 22-year-old woman, with me being a 24-year-old guy at the time. I was used to being surrounded by quirky people, so her online messages never set off any major flags.
I drove by her place to pick her up at night, so I never saw her until she was in my car.
First, Lilly informed me she preferred to be called by her demon’s name, Lilith. Lilith was 50% demon, 40% vampire, 5% werewolf, 3% human, and 2% other. She was tiny; instead of being 22, she just had her birthday the week before and turned 17.
She was also seriously pregnant! She was seven months along, which made her belly bigger than the rest of her—with child number three!
Krakenimages.com, Shutterstock
36. Memories Of Middle School
My very first date was when I was very young. I don’t even know why she said yes, but I had a crush on this girl for the longest time, and everyone knew. We picked a date and time, and the plan was to hit up the local pizza place and then watch a movie.
So, my lanky, stinky, middle school self got all dolled up and ready. My mom drove me to her place, and I awkwardly waited around for her to get ready.
It was then revealed to me that she was bringing a friend. We got into the car and made our way to the movies. The entire trip is super silent and awkward—and things only spiraled from that point on.
My mom was the one trying to make small talk with everyone, and it was certainly not helping. She dropped us off at the pizza place, which was directly across the street from the theater.
I ordered two large pizzas. I was sitting across from two girls who were very nervous and not the most social people. You’d think the third person would make it easier to have a conversation, but absolutely not for a bunch of teenagers.
They each had one slice of pizza, and I tried to make up for the difference and ate like four.
We had to throw out some slices, and I wound up giving a whole pizza to these random people in the restaurant on our way out. We went and watched the movie and still hadn’t really spoken a whole lot by that point.
When we got out, we waited around for my mom to pick us up. Then, my teenage brain thought the natural next step of our date would be a kiss.
I hadn’t asked my dad about this specific situation, but the conversation had come up a while before. I remembered my dad saying I should ask if I could kiss a girl before doing it.
So, as we were waiting around, I had to find a way to make my move where it was just the two of us. At least I had the foresight to not do this in public.
We walked over to the town’s covered bridge, and I asked her if she was enjoying herself. She said yes, and I leaned in and asked if I could kiss her.
She was obviously nervous, and she just said, “No, thank you”. So, I had to reverse the lean-in technique to make it look like I was just trying to reposition myself. I said, “OK,” and we made our way back to the parking lot of the movie theater.
The car ride home was exactly as awkward and silent as the ride there. We still acknowledged each other’s existence at school, but whatever thought I had for her in my little emo heart was completely replaced with, “I think I’ll hold off on the dating thing for the rest of my life”.
37. I Booked It Outta There
Back in college, a guy my jerk sister’s rat fink boyfriend set me up with took me to the public library. I’m a good sport who likes to read, so that wasn’t a deal breaker.
The worst was fending him off when he tried to grab a feel in the YA section, listening to him brag about frisbee golf, and then making me WALK a mile from said library for Chinese food.
He ordered $60 worth of food I didn’t want and had the gall to pretend to search for his wallet when he had a square wallet-shaped lump in the back pocket of his jeans.
After admitting he wasn’t going to pay for the food he ordered, he talked about all the “activities” we could do together in his dorm room. I didn’t say anything. I just paid for the food and let him walk me to his dorm.
When we got there, I said goodnight and left with the entire Santa sack of food. I had a good cry on the walk home once I was out of earshot of his swearing.
My sister and her boyfriend chewed me out for being rude until I showed them my fridge full of egg rolls and explained that I hoped they liked Chinese; my monthly food budget they mooched off of was spent.
In defense of the Chinese place, they made excellent orange chicken, but that was by far the worst date I’ve ever had. I hope his frisbees melted in the sun.
38. I Tried To Get Him Off My Chest
Within five minutes of sitting down to meet me, he decided to comment that I had a huge set of knockers. He mostly talked at my chest while I tried to finish my food and get out of there.
Right after the date, he sent me an unsolicited picture of him without any clothes, cupping his junk, then demanded I return the favor because he sent one. I blocked him.
39. Going Down A Rabbit Hole
A guy spent the whole date talking about his pet rabbit that he loved so much that it slept in the bed with him. When I tried to talk about something else, he would interrupt me and talk about the rabbit again. His whole life revolved around this rabbit and nothing else.
40. She Wanted A Little Afternoon Delight
We went on a lunch date. I wanted to keep it casual and low stakes, just a meet and chat. She asked me back to her house after lunch. It was, like, 2:30, and I thought, "What the heck? Have a Coke, get a feel for who she is, and chat a bit more. Sure. Innocent enough".
It turned out she wanted to enjoy conjugal relations with me—in her bedroom—with her 8-year-old kid who had just gotten home from school—watching TV in the living room. I declined the opportunity and left pretty abruptly, and that was that.
41. It Was A Blunt No
We had a great first date and with great conversation. Then, on the car ride home, he started playing James Blunt's “Goodbye My Lover” on repeat. He teared up and said it reminded me of his ex, who he can’t get over, but really loved the date and thought I was beautiful.
He then proceeded to play “You’re Beautiful” by, again, James Blunt. I honestly got out of that car so fast and thought even the best of comedic writers couldn’t have made up this situation.
42. A Date With Doctor Strange
I was forced by my mother to go on a date with a "childhood friend". It was more like it was somebody I grew up with who I didn't really talk to too much but was the son of my mother's friend.
My mom wanted me to try to date him because he was a doctor and a good Christian man, according to her. What she didn't tell me was this man was pretty much insane.
The first thing he told me was that the reason that women have period cramps is because of their knockers, and the bigger their girls are, the more painful period cramps are. So, he wanted a girl with a small chest so that he wouldn't have to deal with her whining.
Meanwhile, I am very much a curvy woman. I wanted to leave quickly. Luckily, I was not forced on another date with this man because he said some other weird stuff that made me question how this man was a doctor.
43. Knock Me Up
I was on a normal, cute, polite first date. Dinner, drinks, music, and walking her home. I went in for a quick bathroom break before heading home. I stepped out of the bathroom to her without any clothes on, jumping on me, licking my face, and begging me to “put a baby in her”.
I never felt so conflicted and yet ran so fast in my life before.
44. Ex This Guy Out Of My Life
I was on a date with this dude, and his ex just showed up in the middle of our meal to give him his garage door opener. The guy clearly had no idea how the ex knew where he was, but the ex clearly knew we were on a date. It was really freaking weird.
He was a nice dude, I really liked him, but it’s kind of just ruined it for me. I'm pretty sure his ex was stalking him, and I didn’t need that in my life.
45. A Slice Of Reality
He used his pocket tool to slice me a piece of cake and later scraped some clumps of dirt off his shoe with the same edge. I asked him if he ever cleaned it, and he replied, "No, why?" He also confessed that he was madly in love with me the same day. We had just met.
46. Captain Needy Pants Sunk Our Date
I met a girl on OkCupid. She seemed pretty down to earth, and we had a lot in common. We chatted for several days through IM and emails, and I asked her if she would like to meet up and get dinner. She agreed, and all of a sudden, she turned into Captain Needy Pants.
The two days leading up to the date should have been my automatic red flag. She texted me CONSTANTLY and would say things like, "I can’t wait to see you".
At first, I thought it was cute, but after five texts in one day saying the same thing, I thought she was getting a little out of control. I almost canceled the date because I was getting mega creeper vibes, but I decided not to.
She showed up at the place we agreed to meet, and she looked WAY hotter than her pictures. The date started off pretty well, and we were having a good conversation. I started thinking, "Maybe she was just genuinely excited to meet me".
Then, 25 minutes into the date, she reintroduced the crazy side of herself.
The first thing she said was, "So...what are we doing tomorrow night?" I was not sure how she meant it, so I laughed and said, "I'm sorry, I have plans tomorrow night". That was apparently the WRONG answer.
She slammed down her fork, and she said, "You are going out with some other [woman] tomorrow, AREN'T YOU?" I wasn't even sure what to say, so I squinted my eyes a little and leaned my ear towards her, and said, "Excuse me?"
She went on a rant and proceeded to chew me out about how I was a horrible boyfriend, and how all she wanted in life was for me to love her. I finally was able to get a word in and said, "I am NOT your boyfriend. This is our first date! What is wrong with you?"
I got the bill from the waiter, handed him $60, and started to leave. She followed me out and tried to stop me.
I was like, "I am sorry, but I need to go". She started crying, grabbed my arm, and would not let go. At some point, she was actually on the ground with a strong grip around my leg, BEGGING me to give her another chance.
I finally broke free, got to the parking deck, and drove away. She was standing at the exit to the deck with tears streaming down her face, screaming at me.
I rolled up all the windows so I couldn't hear her. I drove away and was so thankful that the date was over. She continued to bombard my phone for the next week and a half. I finally had the number blocked by Verizon, and the drama stopped.
47. The Pizza Purist
We met for dinner and somehow got on the topic of pineapple on pizza. He was very enthusiastic in saying that anyone who likes pineapple on pizza are heathens and should be culled from the earth.
I laughed, thinking it was a joke, and said, "Well, I like pineapple on pizza". Big mistake on my part.
It was apparently not a joke, and the rest of the dinner was painfully awkward and quiet. We clearly both wanted to leave as soon as possible. We never spoke to each other again.
48. The Pee Watcher
On my first date with this girl, I excused myself to use the bathroom. She got up and followed me, making flirtatious remarks along the way. I thought nothing of it, assuming she needed to use the restroom, too, and was just making small talk.
I walked inside the men's room, and she walked straight in with me. I said to her, "Um, I actually do need to use the restroom". She said, "Oh, I'll watch". "No. Just no". I was not able to pee in public for a while after that.
49. Midnight Madness
I met someone online who I thought was really great, and after texting each other for two weeks, we finally met in person. He picked me up, we had an awesome time and decided to go back to his place.
As we were nearing his place, there was almost no one else on the road when all of a sudden, this other car came out of nowhere and cut us off. The reason why was quite disturbing.
Apparently, everyone knew each other and had some kind of major beef with each other. He threw his car in park, broke out the tire iron from his back seat, and there were three guys trying to get at the guy I was with.
Fists were flying, people were bleeding, and I still had no idea what on earth was going on.
We went back to his house, and he immediately woke up his parents, who came out. It was like 3 am now. This was still our first “date,” so now I was also meeting his entire family. And the cherry on top? The authorities showed up.
They didn’t cuff him but told him he needed to come down to the station with his parents.
There was a discussion amongst all of them, his dad agreed that he would personally drive him to the station after they swung through my date’s methadone clinic first as soon as it opened. Then he dropped my date off at the station and drove me home.
It was a very awkward car ride back with my date’s father, whom I just met.
RealPeopleStudio, Shutterstock
50. Blind Date Debacle
I was on a blind date arranged by a mutual friend. When I got there, she was already eating appetizers. I was 10 minutes early! Then, she ordered the MOST EXPENSIVE dinner on the menu and told me she did it because she knew I was paying.
Small talk failed, and for 45 minutes, she complained about how no one was refilling her drink, which she guzzled every 20 seconds.
She mentioned how she was told that I made a decent salary MULTIPLE times. I tried to be civil and change the subject. Awkward conversational topics ensued, and nothing even close to first-date etiquette followed.
Three-quarters of the way through, I went to the bathroom, and our waiter walked by and asked me if we were doing a reality show since he had seen the disaster in motion.
We talked about how wild this woman was, and then I asked him to stop at our table and ask about the bill. I immediately said split checks and gave him 80 dollars (roughly $40 for my bill and $40 for his tip).
The date looked shocked and ended up not being able to pay her bill, so the friend who hooked us up got a call and flipped the rest of her check. Her total came to be about $75. Last blind date ever.
Sources: Reddit,
