24 People Share The Craziest Thing That Ever Happened To Them On A First Date. Check Please!

It's usually a bit awkward to get to know somebody for the first time, but it's especially bad when you're trying to figure out what your romantic potential might be. this means that first dates, when they're bad, are simply the worst.

Here are twenty-four of the craziest and most cringeworthy things that happened to people on the first date.


Many thanks to Reddit users monkeymagnet & ScubaCam for posing these questions. Check out ore from the source at the bottom!

1/24. My name is Andrea, his name was Sam. I though he was a girl, he thought I was a girl as well. Realised we were two dudes and said goodbye to each other.


2/24. He pulled out his penis in the middle of a full movie theater.


3/24. She invited me to her place where she began smashing mirrors with a ball peen hammer for some crafty therapeutic mosaic she was working on.

After a call and argument with the downstairs neighbors, the cops arrived. One cop took me aside and said "We get calls about this lady all the time. You may want to reconsider hanging out with her."


4/24. After dinner as we're walking to the car he puts his arm around my shoulders. I'm wearing a tank top therefore have bare arms. He strokes my arm and looks at me, completely serious mind you..."Your skin is so soft, I wish I could cut this piece out of you so I could feel it all the time".

Big what the f*ck moment for me and no we didn't see each other again after that night.


5/24. We went out to a local wine bar. Everything was pleasant enough during our time there, although there were a couple minor red flags. However, when it came time to leave and the valet pulled the car around, she reached her closed hand out to him, palm down, and said, "You like Adderall? These are 30's."

The guy's eyes got absolutely huge. He looked at me and then back at her and said, "No. No. No thank you," and withdrew his hand really, really fast. I was (and am) dumbfounded.


6/24. Not exactly a first date, but an odd experience that prevented a first date from ever taking place.

I used to be on OKCupid before I started dating my current girlfriend (we met IRL, not over OKC, but that's irrelevant). I have a pretty high match % with this one woman, her picture is pretty cute, so I click the profile.

Nothing out of the ordinary at first, she seems cool. Then I get to the bottoms of the profile where there is what can only be described as a disclaimer. It read something to the effect of: "FYI this account is operated by my father. I do not have the password, and he will be the one checking it. You will have to meet with him one-on-one at least once before you get to meet me, with him present. Do not message me if you've ever had sex outside of marriage, if you've ever looked at pornography, or if you're divorced for any reason other than your wife abandoned you."

She was 27.


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7/24. The date was arranged by the college newspaper where I was attending school. I had never met, nor seen the person who I would be courting that night. I was only told that all expenses would be paid for. I was a college student - how could I turn down free food? We met up at a local greek place while being followed by a film crew.

She was great - charming, cute, funny, and could hold her own in a conversation. However, much like that exact lego piece that you really need in a tub full of legos, her crazy was well-hidden. After the meal we went for a long walk on the beach. A few minutes into the walk she leans in close and whispers, "let's ditch the film crew". When a girl asks you to find a way to get to a secluded place, logic is overtaken by hormones.

The second they turned their heads we made a dash for it. We found a lifeguard tower that wasn't in use and made our way up the ramp. It was perfectly secluded, and it had the tactical advantage of being able to see if anyone was approaching. I leaned in a for a kiss, expecting that was what she wanted. She put a hand to my chest and held me back. "Wait," she said. She was excited at this point and she made no effort to hide it. "You want to see my scars?"

No biggie, I've had creepier things said to me and I figured it was an excuse she was making to eventually get us undressed. I was game, "sure...!"

She took off her shirt. All across her stomach we DEEP scars that scored her abdomen like cordoroy. Scars so deep they didn't just change the tone of the skin, but changed the underlying shape of it and how it flowed. "Want to give me one?"

"I... er what? What are these from?!"

"Memories. Give me one!"

She pulls out a hunting knife from her purse. The crazy was no longer hidden. She actually wanted me to cut her abdomen open.

"I've done it before, we'll just say that I fell while we were climbing the lifegaurd tower."

"I... I think that the film crew found us."

They were a good fifty yards away and were oblivious to the fact that were were there. I stood up and waved, faked a blush like we were being naughty as this half-naked woman with a knife was hidden below me. She was not pleased, and had a knife. I was mentally saying goodbye to my currently not-stabbed body, and was praying it would stay that way. The cameras were on though, she knew she had to play nice. She hid the knife, stood up, and giggled.

The date continued.

We played laser tag.

I elected not to give her my number at the end of the night.


8/24. My first date ever, I met his entire family, which coincidentally included his older brother's fianc who also happened to be my guidance counselor. Fun date, but also awkward.


9/24. On my first date ever, I pulled the chair out for her. She didn't see and fell to the ground. You know those times where you aren't supposed to laugh? Turns out that was one of those times.


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10/24. I met a woman at a restaurant on a blind date. We ordered and she turned to me and said "So when are you going to propose?" My answer of "Well this is our first date, so I haven't thought further than dinner" upset her, so she left. Ten minutes later she came back and said "Well you upset me, but you can still buy me dinner".

Again my answer upset her ("I can. I won't").


11/24. I went to pick up a girl for our first date and she was dressed in a stormtrooper outfit. It was not Halloween, nor was it some sort of event that one would expect to dress in costume. We went to Red Robin.

The funniest part of that story is that I showed up to a date where a woman was wearing a stormtrooper outfit and said "eh, what the hell?"


12/24. My wife of 21 years got pregnant on our first date.


13/24. Her: I hope to join the army in a few months.

Me: Oh yeah? What do you want to do?

Her: I want to kill them.

Me: Huh? Kill who?

Her: The Iraqis. I want to kill them for what they did to us. I want to bomb them all, I don't care if they are civilian or not.

Ooooohhhhhkay, goodbye.

I am sure this is her perspective:

Some anti-American douche walked out on me because I wanted to serve my country.


14/24. A girl sucked on my tongue and tore my (thing underneath the tongue) frenulum resulting in a mouthful of blood.


15/24. Blind date: She kept murmuring encouragement to herself: "This is going okay." "See, you can do this." "Okay, everything is still fine."


16/24. A girl wanted to know why I hadn't found God. (kind of a 3rd date question, don't you think?)


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17/24. I don't know if this is weird as much as just disastrous, but years ago I took a girl from a class I was in out to the movies. At the local indy cineplex they were showing two movies: "Boys don't cry", and "High Fidelity". I said, "Oh, high fidelity, that's supposed to be great, let's see that." She says, "No, let's see Boys Don't cry". I said, "Well, that's supposed to be a good movie, but it's really dark, let's see something funny". She looks at me and says, "NO, I want to see boys don't cry".

Uh oh.

Sure enough, while it is an amazing film, she is sobbing, SOBBING 2/3 of the way through it, like body-shaking-tears-pouring-down-her-face-hunched-over sobbing. I think I could have drowned puppies in front of her and not gotten that level of reaction.

Now, I'll cry at a movie now and again, but only when the time is right, and certainly not when I'm wildly uncomfortable that this girl I barely know is hysterical next to me. I do my best to console her, and after the movie, her first question is, "Why aren't you crying?" "Well, I was kind of worried about you, it distracted me" "Seriously, why aren't you crying?" "I'm serious, it was an incredibly upsetting scene, but I was worried you weren't okay"....this goes on and she gets visibly annoyed that I didn't cry.

Should have bailed then, but I decided to try to salvage things, and said, "Hey, tell you what, it's still early, let's go get a drink, relax a little, talk about the movie". We go around the corner to my local Irish pub, I walk in, bartender says, "Hey, the usual?", and my date turns and looks at me in complete disgust and says,

"What are you, some kind of alcoholic?"


18/24. I'd met a really nice guy near where I work. We went for coffee during the week. Everything seemed to move along great. He invited me to dinner on a Sunday. He picked me up, and we went to a nice place. We had just got our menus when his wife showed up.

I had no idea he was married. It wasn't like divorced, or separated, or anything like that. She went off on him right there in the middle of the restaurant.

I've never been so embarrassed. I just walked outside and called my sister to pick me up.


19/24. I went out once with one of my customers while I was working in a video store. The date started out really nice, he actually made a picnic and we went to a nearby park and set it up. The conversation flowed well, food was good ... then he asked me if I had roommates. I said yes, told him about the dorms, etc before politely returning the question and asking him if he was living with any roommates. Completely nonchalantly he replied "Yes, two. I live with my wife and daughter," and then proceeded to change the subject as if this was just kind of no big deal.

I thought he was joking at first, so I sort of sat there dumbstruck until I finally confirmed that he was indeed married with a daughter. When I asked him what was wrong with him, and told him I wasn't interested he replied by asking me if "I'd just please go down on him."

I sort of laughed a little and shook my head before I quickly high tailed it to my car, and I never saw him come into the store again.


20/24. I was at a party and started talking to a friend's attractive coworker. Everything was going fine, but it got a bit weird when she said "If we're gonna be friends, you're gonna have to buy me some jewelry."

She seemed to have a really dry sense of humor, so I didn't even consider that she might be serious. I laughed and played along by asking what she wanted but then she started talking about the specific piece of jewelry she wanted. Somewhere during her detailed description I started to realize that she was being dead serious.

Then she told me the price. I excused myself.


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21/24. Okay well our first date was on Valentine's day, you know, that gloriously overplayed day of love? We sit down, and the first personal story he divulges to me is one of how he got a urinary tract and kidney infection from masturbating in the shower too much....

We dated for 6 months after this, as I found it to be hilarious.


22/24. I went on a date with a guy who took me to the movies, and then back to his parents' house. After the movie he barely talked to me, other than to show me his room of instruments and show me how he could play the Spongebob Squarepants theme on a penny whistle.

After he dropped me back off at my house, he sent me a ton of messages about how he was sexually frustrated and wished he would have sucked on my face instead of the popsicle he had to buy to relieve all of his pent-up sexual desires.

You stay classy, high school guys.


23/24. We were 23. He was hot. Tall. Ripped. Not very smart but hell, I was horny. Our first date consisted of no conversation at dinner. Not one word, other than food orders. I gave up talking and decided to enjoy the meal figuring this was over before it started. We finished- and then we go outside to the beach.

I start to say bye when he suddenly pulls me to him and starts kissing me. Then he pushes me away and starts sobbing. Like gasping, gulping sobs that echoed around the beach. He kneels in the sand and I get down by him pretty concerned, thinking that maybe someone died or something traumatic had happened. Then he starts talking. His previous GF (of two whole weeks) had decided to see other people. His crying got louder and he started pounding the sand with his fists.

I tried to calm him down at least (and shut him up), and ended up playing counselor for a few hours. He called me every night for a week after that and wouldn't talk. Just cry.


24/24. She talked about her extensive machete collection and how she's threatened some of her ex's with them just for fun. She also talked about how she got the massive scar on her arm for punching out a window. Her friend just sat awkwardly the whole night and got hammered. I felt bad for her since she didn't like being the third wheel.

Here's the fun part though, since I was bad about ignoring red flags at the time, I tried to organize a second date. However she acted like she didn't know who I was and that we had never met.


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