The Most Outrageous Date Moments Of All Time

While dating can often offer up awkward and beautiful moments in equal measure, on occasion a date can leave everybody involved in total disarray.

Whether it’s a joke gone wrong, an unexpected third wheel or an ill-judged revelation, plenty of people have a tale or two about when a date made their jaw drop.

What’s more, any date can be ruined by an Act of God – where no one could have possibly anticipated the disaster they were walking into. As told by Reddit users, here are 50 of the worst moments ever experienced in the world of dating.

1. Prompt feedback

After our first date, he gave me a verbal report card in the car. One of my negatives was that “I took too small bites.” Apparently my good table manners made him nervous? But one of my positives was that it seemed like I liked to be in the kitchen?

About 2 hours after the date he called me to tell me that he had looked through my entire Facebook and read all of my blog. He had decided that I was cooler than he’d thought on our date so he call the girl he had plans with the next night and dumped her to hang out with me more.

Needless to say there was no second date.


cheese served on tray

2. Fine dining

I was on second date. This guy said he wanted to cook something elaborate for me.

I met him at his house, he shows me his freezer and asks me to pick a frozen dish which he then puts in the microwave for me. Seriously wtf material.


3. Saved by a stranger

I told a guy about my mom’s upcoming surgery (not life threatening). The guy said to me, “Well, because of where you grew up, maybe a death in the family would serve you well. You know, a character builder. People like you could really learn from that.” So he wanted my mom to die? Great.

Then he goes on to tell me a sob story about drunk driving and being in a coma and how he turned his life around. Bartender asks for his ID…I notice it isn’t a license. I ask about it, and he says he got a DUI a few weeks ago.

I could keep going. This date was epic. I ended up being saved by a stranger in the end who was witnessing my misery.


4. Supernatural beliefs

We decided to meet at a starbucks and convo was good until he started doing an impression of the Joker. (I’m already freaked out at this point and ready to leave) Then he asked me why I hadn’t drank my coffee yet, and I said it was still hot. And he apologized, because he was in control of the heat/fire around us. I was intrigued at how ridiculous this was and let him continue.

He told he he first learn of this when he was in his car and the car windows steamed up. I was trying so hard not to laugh. I politely said well this was fun, but I need to get to work.


5. Strange question

I went on a date with a girl and during the date she showed me pictures of her boobs and her mom’s boobs. She asked me which were nicer. I’m still not sure what she’s doing with pics of her mom’s tits in her purse or why she cares what a first date thinks of them…

I did not go on a second date to find out!


6. Just one concern

Once I went on a first date and the guy told me that I seem great, he just had one concern: “I’m not saying you’re fat, but I’m worried you will gain weight and not be attractive to me anymore.”

I was 110 lbs at the time. And I was eating a salad.


7. Low score

I had a gal ask me what I looked for in a partner. She seemed annoyed that my answer was rather general, and proceeded to pull out her list.

It was 8 typed pages. She started going through them and giving me check marks. I didn’t get very many.


8. Not to be trusted

Worst date I’ve had.. well I take it back, the date itself was awesome! We hit it off and had a lot of common interests. It was the end of the date that sucked. She asked me at the end of the date what my facebook name was. I told her, honestly, that I don’t have Facebook and don’t have one (I still don’t). She looked shocked.

Anyways, since the first date went great I asked her out again a few days later and she flat out told me no, because and I quote “I can’t trust anyone who doesn’t have a Facebook account.”

Soooo glad I avoided crazy that early on.


9. Chivalrous mishap

I have shoulder problems… I have had three different dates with three different women that ended with me in the ER after a major dislocation.

Once I dislocated my right shoulder when I went to hold open the door for my date on the way into the restaurant. Shortest date ever, she drove me to the ER and as I walked in, she walked toward a bus stop. Never saw her again.


10. Upsetting discovery

I once went on a date with this girl. We started with a movie.

After the movie finished, as we were pulling out of the parking lot, she saw her father leaving the same movie, with a woman who wasn’t her mother.


11. Speeding fine

I was on a first date with a guy I liked, and while he was driving (red Mazda miata) he got a speeding ticket and asked me to pay for it, since I was talking and he was ‘distracted’ from the road. I was annoyed, but I took the ticket.

He then took me to dinner at Hooter’s and asked me to pick up the tab so he can pay for us to get into some night club, where he spends the entire evening talking about other women he’d been with. Needless to say there was no second date.


12. ‘Live a little!’

First date going well, making out a little when she licks the contact lens out of my eye. I’m like, you just licked my eye, thinking she made a mistake, to which she responded “live a little”???

I kindly asked her for my contact back, she said eyeball licking was a hot turn on. No more dates with her after that.


13. Odd priorities

I was on probation for an undesignated felony (means that it can be changed to a misdemeanor after probation if the judge thinks you deserve it) for a while. During this time I went on a date with a girl who I met in art class. During dinner I told her about probation and she was curious but fine with it.

After dinner on the way to a movie a Christmas song came on the radio and for some reason she asked me about going to church on Christmas and I told her I didn’t go to church. She slowly put it together that I “didn’t believe in anything” and immediately the date was over…

Forgive me but I think she should have been more upset about the felony than the heresy.


14. Arts and crafts

On a blind date, the guy pulled out a knitting project and started knitting. When I asked what it was, he told me it was a uterus for the life-size human body with removable organs he was making.

He then texted two of his friends to invite them to our dinner. Needless to say, there wasn’t a second date.


15. Meeting the family

My boyfriend (now husband) and I got serious very quickly, and after a few weeks of dating, he took me abroad to Italy to visit his mother.

After the initial helloes and air kisses were finished, she touches my ears, face and neck, and then gestures to my hips with a wide grin and exclaims: ‘She has small ears, good teeth and wide hips, but wow… what a funny long neck she has! Still, she’s good’.

Apparently, I was approved. I felt even weirder when my husband said, ‘I knew you’d love her, Mom’.


16. Wardrobe disaster

I went on a blind date with a girl I met on the internet. I dressed up nicely and wore my fancy mink coat (whole different story how I got that). I met her in front of the Bellagio, at the fountains.

When she arrived and introduced herself, she asked “is that real?” to which I replied “Hell yeah it’s real.”

…awkward silence..

Girl: “I’m a vegan.”

It was THE most awkward date I have been on. We walked around talking for a couple hours, but every once in a while she would look down at the heap of dead animals I was carrying around and give me the stinkeye.


17. Awkward encounter

On my first (and last) date with this guy we went to a nightclub.

When we got there he recognized an old friend and started talking to her, he introduced me to her as “His old buddy who taught him everything he knows in the bedroom”.


18. Driving a date away

I once had a blind date with a guy and it went well. At the end of the evening he told me he was so glad he didn’t “turn around and drive home” like he almost did when he saw I drove a truck. I asked why that would be a problem, and he said, “Because people who own 4 wheel drives and don’t need them are jerks.”

I was a hospice nurse at the time, serving a 100 square mile area that included many farm homes, and was on dirt roads every day. I made emergency visits often, and rain/mud would have stymied my previous car (a Camaro). Plus, my truck was not 4 wheel drive, but even if it was, I had every right to have one. He drove a 4 wheel drive. I asked him when the last time was that he was on a dirt road, and he couldn’t tell me. Hypocrite.


19. Bomb threats

I went out on a date with a guy that had gone to my high school, but was a few years ahead of me. It turned out that he had to get his GED because he was expelled for calling in numerous bomb threats my sophomore year. He didn’t say why he called them in either, just that he did.

I found out that day that my best friend will in fact drive 30 minutes in pouring rain to rescue me from a bad date.


20. Premature love

At the end of a mediocre blind date with a guy who was giving off a slightly needy vibe, he gives me a peck on the cheek and a greeting card in an envelope. I get home, open it, it’s an excessively romantic card that says “I knew from the first time I saw you that WE WOULD BE TOGETHER FOREVER.”

I can’t tell whether it’s more creepy to think that he hadn’t seen me until after he had purchased the card, or that he’d stalked me before our date.


21. Body-shaming

There was this girl that I was talking to once awhile back.

She’s known to have high standards when it comes to, well, everything actually. Anyway, she and I had a thing for each other but it didn’t work out since the only way for me to be accepted as her boyfriend is to gain some weight.

I’m skinny as hell and for her to give me an ultimatum by gaining weight in the end of the week just so we could be in a relationship is so stupid.


22. Night-time visitor

I went out with this guy once, not even a real “date”. Just meeting up for a few drinks, great conversation, good times…so good in fact that we ended up back at my place playing video games after the bar closed, it could have been love.

Two nights later he broke into my house at 3:00 in the morning with pizza rolls to see if we could hang. I wasn’t really into it, my 3 female roomies, even less. He did this three more times, more pizza rolls, burgers and nachos. Oh, he also walked right into my bedroom with these 3AM gifts.


23. Being watched

I went out on a first date with a girl I had been talking to for about a month. I took her to her out to her favorite, really expensive restaurant.

Later, I find out she had friends go to the same place to watch our date. She told me this because her friends didn’t think I was attractive enough to be with her.


24. Evil agenda

Once went on a date with a guy I met at a bar. He was cute, good personality, we had some good jokes and even had mutual friends. Five minutes into the date he bluntly asks me, “So what’s your agenda?”.

I thought maybe he meant life plan, but no. He wanted to know exactly what I planned to do to sabotage him and any potential relationship. Needless to say, no second date. Running joke with the current beau about my evil agenda and how it’s all coming together with him.


25. Star-crossed lovers

My date was not really interested in what I had to say. When I confronted her about it she said there is only one thing she really wanted to know. Out with it, I say.

She pulls out a clipboard; it even had a pencil on a string. She proceeds to fill out an astrological chart, asking me questions along the way. After we are done she informs me that there is no reason to talk any more and that she will be contacting me when she has analyzed the data.

I never called her back when she called me a couple of days later and missed out on learning what she came up with.


26. Funny animals

I was on a first date with a girl walking around a mall that had an indoor ice skating rink. We stopped and watched toddlers falling down and whatnot, and I said “Humans sure are funny animals”.

She started crying at that. Humans are made in the image of God of course, and she was upset that she liked me too much and I was a heathen.


27. Generation gap

My date, a handsome writer spending time in Berkeley, was shocked to learn that I didn’t know who Buck Rogers was.

Yes, he was older than me, but really? Buck Rogers is your standard? Your cut off point? As a fan of the original Twilight Zone and Richard Matheson, I was genuinely confused.


28. Mystery creature

My first and only blind date, we were killing time before a movie in a nice park. We were just walking and talking. I saw some ducks, and said “look at those ducks” she looked at me with a straight face and said…

“What is a duck?”

This girl was local to the area. After she said that I just ended the date and went home lol.


29. Favourite book

I once dated a chick who was.. Just bizarre. I accepted it at first, we met over the internet and we were very good with each other’s company…

We talk about favorite books later on in the relationship: [I ask her] “what’s your favorite book?” “Harry Potter.” “Oh! I never really got into it that much, though..”

“..You hate it?” [she asked]. “No I -” “I’m sorry, but if you hate Harry Potter, we can’t be together.”


30. The good part

This guy once forced me to watch a video on his phone of him playing the drums. In the video he was topless, sweaty, and gross.

He made me watch the full 10 minutes, and kept saying “Ooh this part is good, watch!”


31. Lookalike

Guy from high school had a thing for me though I thought he was kind of obnoxious. He goes to college (a year older than me) and then wants to take me out when he’s home for the summer. I very reluctantly said yes.

His sexy swimmer body was no more. As required by the UNC Chapel Hill dress code, he was wearing a polo, khaki shorts, Croakies, and Sperrys. The first words out of my mouth, “Oh my God, you look like my Dad!”

Nailed it.


32. Exchanging revelations

I went on a blind date with this guy, and it wasn’t terrible but it wasn’t great either. He was nice enough, but there just wasn’t any spark and we didn’t talk too much about personal stuff.

As he was driving me back to my house, I told him that I wasn’t looking for anything serious right now, hoping to soften the blow because I didn’t really want a second date with him. He replies right back, “I have something to tell you too: I have genital warts. But don’t worry! They’re not contagious!”


33. Getting a reaction

I had been out on a couple dates with this guy and we were going to see “New Jack City” in a not too nice of a neighborhood in the L.A. area. For some reason we took my car and half way there, he says “aww shoot, I forgot my toy gun in my car. I was bringing it to see if I could get a reaction at the theater.”

Fast forward to when I get home, I just left him and went inside, as he was pulling away, my mom sees his car pulling away and freaks out a bit and says that some kids playing saw a gun in his car and the cops were called and they broke in his car and took the gun. Later he calls me to say that my neighborhood must be bad since his gun got stolen……idiot.


34. Lacking in sympathy

I once met a girl at a show who I thought was pretty cool, made plans with her for the following weekend when I was going to be in town.

In between those two situations I ended up in the hospital with a collapsed lung (spontaneous pneumothorax) told her I would not be able to go out with her because I was in the hospital and she never talked to me again.


35. Quick to judge

Not really a date story, but some girl I met during studies said something along the lines of “I don’t think we should be together, I don’t think we would work out”, after knowing me for three days or so.

I was a bit dumbfounded, so far I couldn’t even remember her name yet. So I guess yes, she was right. I still don’t know how she got to that idea. On the other hand, I think she said it when drunk.


36. An expensive evening

To keep this very short… I picked up this girl and took her to a famous in-town sushi bar. 130$ Bill, I paid. Took her downtown for chocolates and sweety delights, 70$ bill, I paid. Took her on a night boat ride around the harbor, 80$ bill, I paid. Keep in mind we did not kiss or do any touching what so ever, not even a hug. She seemed put off by any hand-holding.

At the end of the night I drop her off at home, she shakes my hand, says thanks for the date, and says “What’s the name of the sushi place again? I must tell my boyfriend to take me here!”


37. Embarrassing comments

Years ago, before I got married, I met someone through a dating service. The guy was quite a few years older than me and had grey hair. At our very first date in a bar-restaurant, some friends of his stopped by the table and made a joke that he was robbing the cradle.

As if that wasn’t embarrassing enough, he then replied, “Oh no, actually, she’s robbing the grave.” Needless to say, that was our last date.


38. The weirdest collection

Met a girl at a bar and we hit it off. She’s weird but a total knockout… spends a lot of time outside teaching kids.

So we get to the restaurant and order a few drinks and appetizers. She goes to reach into her bag and a small vial filled with black fluid pops out, rolls across the table and falls under the table of the couple next to us.

I ask her what that was.



Apparently they have a competition to see who can pull the most ticks off of their students during the summer. She had two vials filled with ticks in her bag, one of which was now under another person’s table.

We’re still dating. I’ve gotten used to having lots of dead bugs around.


39. Stay-at-home dad

I went on a date with a girl I met online. We met up for dinner, and throughout the entire thing I felt like it was more of an interview than a date. She kept talking about how much she wants kids. Kids this, kids that, she loves kids!

Well, I wasn’t really feeling it, so when she asked me what my goals in life are, I said “I’ve always wanted to be a stay at home dad. But to be honest, the kids are optional.” She looked like I just lit a puppy on fire right in front of her.


40. Odd location

It was a first date with a guy I had met in a class in college and he said he wanted to take me out for ice cream.

All’s good and dandy until we show up to the hospital and ate ice cream in the cafeteria.


41. Good manners

So, I had this date with a girl, pretty standard events, things went well enough that we went back to her place.

Sexy fun times.

Sexy fun times ruined by her stopping every time her cat sneezed to say bless you…


42. Too nice

I got in to bed with this girl on our 2nd date, just sleeping. Then she dumped me 2 days later claiming she actually wanted to use me but thought I was too nice a guy.

If you ask me, I was not used enough, but the whole thing was so weird I just decided to move on to someone else.


43. Threatening call

My date got completely drunk out of her mind EARLY. This was in the days before GPS, so I had written down the address where she lived. I at least was able to take her home and help her into the house.

Left her house key on the floor right on the inside throw rug. A day and a half later, when she finally sobered up. she called me up threatening me if i didn’t return her house key. Seems her cat had carried it under her brother’s bed.


44. Checking ID

Parents took me out to dinner one weekend my freshman year of college, the waitress was cute and I got up and got her number. Went out a few days later, she carded me to make sure that I was “not a convict or a pervert” and so she knew my real name.

I can’t fathom what happened in her past that precipitated this behavior, but it was very odd nonetheless. There was no second date.


45. Birthday update

First date went great, second date I told her I’m an atheist, she didn’t say anything negative. Come my birthday, I texted her if she wants a third date, she replied that she’ll call me later.

4 hours later, she called, said happy birthday, then said “my morality is not compatible with your beliefs”. I said ok, and ended the call.


46. Job drama

I went on a date with this girl once and in the middle of dinner her phone started blowing up. She apologized and said it was her mom and asked if she could take it.

A few minutes into the conversation with her mom she breaks down in the middle of the restaurant and starts crying into her phone about how tough her job is and how much she hates it and wants to give up. After she got off the phone I tried to talking to her and asked her where she worked. In between sobs she said “Disneyland”. She was 25.


47. Small talk

Not mine, but my friend’s: We were all hanging out in my house, and he decides to bring his date. So, we started talking about how much beer we used to have in college, and just when everyone stops talking he asks her: “So… how many times have you vomited?”…

Needless to say, we almost died laughing.


48. Mixed messages

I had a guy flirt with me for about three weeks (and I don’t mean little things, I mean he insisted on buying me drinks, played with my hair, complimented me constantly, and by the end of week three was very forward flirting wise.) only for him to tell me he has a girlfriend.

He decided to do this while we were watching a movie at his apartment.

And then he tried to kiss me.

When I called him out he claimed he was just socially awkward and didn’t realize I was taking everything romantically.


49. Date gate-crasher

I made a Plenty of Fish account. Talked to this guy for a few weeks through texting, but eventually stopped. A couple months later, I’m out at a bar with another guy, but Mr. Plentyoffish walks in.

He introduces himself, then sulks the rest of the night watching me from the other side of the bar. When I leave, I check my phone and he left me a bunch of angry messages.


50. Real-life Cinderella

One time I went on a date with this girl. She was a Broadway actress (she actually was, she didn’t just lie about that) and incredibly attractive. We go to dinner and eventually we got on the topic of hobbies.

She started explaining to me that one of her favorite things to do is to make Cinderella style dresses, wear them, go outside, and sing to animals.

She told me that she really believed that she was able to communicate with God’s creatures through song and that she was their princess. I didn’t go on a second date with her.