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People Share The First Dates That Were So Strange We Have Second Hand Embarrassment

Whether you are dipping your toe back into the dating pool or are very experienced in the art of dating, it’s important to bear in mind that not all dates will go well. In fact, it’s wise to have a little back up plan to allow you to make a polite but hasty exit in case things are super weird or uncomfortable. It’s also advisable to ensure you let friends or family know exactly where you are going to be, because, if this Reddit thread discussing the strangest first dates people have had is anything to go by, anything can happen! That’s not to say you shouldn’t date. Sometimes, you just have to date a few frogs before you meet your prince!


I went on a breakfast date once. Date orders two sunny side up eggs.

Proceeds to take two straws, poke one in each yolk and suck the yolk up.

Don’t even remember his name (Ok_Airline7121)


The guy saying he was 6’2 on tinder and then when I met him he was short than me, I’m 5’7. I don’t mind that but why you lying about something so obvious LOL (Questionablesam)



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 says, “Are you sure?” I said “Yes”

He proceeds 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 favourite brand of bagpipes, the anatomy of bagpipes…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. (EpicPenguinSharks)


Went on a date with a woman from the office. Thought we had good chemistry and got along well. She couldn’t find her phone so I tried calling it and someone from the restaurant answered. I went back in for her to get it and the waiter showed me I was saved in her contacts under “Free Food.” (Sol_Blackguy)


He asked me how big my baby was and if I birthed him vaginally or had a c-section. His explanation was that he’d never slept with a mom before and had heard a baby can stretch out a vagina. I excused myself to the bathroom and promptly left the restaurant. (gretagogo)


I picked her up and she asked me if we could stop by her moms house so she could “run in and grab something.” I said sure. Made the stop. She went inside. 5 minutes later she comes out hustling towards the car with a carseat and her mom chasing after her yelling. She opens the car door and throws the carseat(which i now see has a baby in it) and starts yelling at me to drive. I freaked and just turned my car off and took the keys out of the ignition.

Her mom called the cops and they came and questioned all of us for a good while. Turns out she had lost custody due to drug use 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 cops left. (Awkward_Ad8740)


Told me that aliens cause jet lag and that I have the ghost of a fisherman following me around named Samuel (on top of the 20 other batshit things she said at dinner. (RVBY1977)


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, very polished, but could not shake that feeling. I drove to the restaurant to meet 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. Gave him money to pay for my half, said goodby when I got to the door turned around and 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 left so he could not follow. Restaurant was on an isolated road so that was safer then having him catch up to me. Found out about a year later he was sent to prison for the assault and rape of 2 different woman . It happened on first dates. Never used a dating site again (Holiday_Horse3100)


He took it out.

And I don’t mean this in a funny “unexpected Seinfeld” kind of way (although I suppose it IS that).

I mean 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.”

And, like an idiot, I LOOKED.”

Then he said “that’s what you do to me.”

I said “this is what you do to me” and I left.

I’m a people pleaser so, to this day, I’m proud of myself for walking away in the middle of dinner. (fansypansy)

The guy told me he would still be together with his kids mum if she had apologized for what she did wrong. Out of curiosity I asked what she did wrong? Was expecting something like she cheated, ya know something that actually needed apologising for.

Nope. Apparently she kept nagging one day and wouldn’t shut up, so, he tied her to a computer chair and went out for three hours and left her there.

I said it doesn’t sound like she was the one who needed to apologize and left. (Pale-Garlic5523)


On the first date, she took her teddy bear with her and started talking to him as if he was alive. Throughout the date, she turned to the bear, asked his opinion and even offered him food from her dish. It was so weird and awkward. (Altruistic-Sun-7778)


Within five minutes of sitting down to meet me, he decided to comment that I have “huge tits” and mostly talked at my chest while I tried to finish my food and get the hell out of there (I really liked the food!). Right after the date he sent me an unsolicited pick of him naked, cupping his junk then demanded I returned the favor because he sent one. Blocked. (Mindlikeamindfield)


When a guy told me I was pretty but I would be unbelievably gorgeous if I lost 20lbs 🤔 (Crownz4mygirlses)


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 didn’t really talk too much but was the son of my mother’s friend

My mom wanted me to try to date him because he is a doctor and a good Christian man according to her What you didn’t tell me was his man was pretty much insane

What are the first things he tells me is that the reason that women have period cramps is because of their boobs and the bigger their boobs are the more painful period cramps are So he wanted a girl with small boobs so that he wouldn’t have to deal with her whining I am very much a curvy woman

I wanted to leave so soon luckily I was not forced on another date with this man cuz he said some other weird stuff that made me question how this man is a doctor (lunachappell)


We met for dinner and somehow got on the topic of pineapple on pizza. He was very enthusiastic in saying that anyone that 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.” 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 eachother again. I sometimes wonder if he became a pineapple on pizza hating serial killer. Probably nearly avoided death! (Celitha11)


Guy spent the whole date talking about his pet rabbit that he loved so much 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. (Mary3883)


We had a great first date, great convo. Then on the car ride home he started playing James Blunt, “Goodbye My Lover,” on repeat. He tears up and said it reminded me of his ex that he can’t get over, but really loved the date and thought I was beautiful, 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. (robertsbrothers)

Have you ever had a first date so awful that a second date was out of the question?


For more hilarious horror dates check out Hilarious Stories of First Dates Gone Awkwardly, Horribly Wrong

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Jolene enjoys writing, sharing and connecting with other like-minded women online – it also gives her the perfect excuse to ignore Mount-Washmore until it threatens to bury her family in an avalanche of Skylander T-shirts and Frozen Pyjama pants. (No one ever knows where the matching top is!) Likes: Reading, cooking, sketching, dancing (preferably with a Sav Blanc in one hand), social media, and sitting down on a toilet seat that one of her children hasn’t dripped, splashed or sprayed on. Dislikes: Writing pretentious crap about herself in online bio’s and refereeing arguments amongst her offspring.

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