Unsplash | freestocks.org

People Share Their Weirdest First Date Stories

Dating can be very difficult for some people. Specifically, first dates can be incredibly awkward as you navigate a minefield of conversational topics in order to try and make yourself look cool and interesting. However, for some people (definitely not me) panic can ensue during first dates.

Someone took to Reddit to find out some of the weirdest first dates that people have had, by asking, "What was the weirdest question you got asked on a first date?"

Unsurprisingly, people had some truly amazing stories to share. So, please find below a collection of the most shocking, uncomfortable, and hilarious responses that people gave.


Unsplash | Josh Appel

"'Are you broke?' While I understand they're probably searching for a stable future, but like, girl... we just met and I'm paying for your food and drinks tonight. Don't pry into my wallet that much yet." — wherethebicenroam

What an unpleasant thing to ask someone on a first date! This person said that they really didn't know what to say, so just replied, "only on the inside."

Mandolin Lessons... If You Catch My Drift

Unsplash | John Lyttle

"'Do you want to come back to my place and play my Mandolin?' And then she meant it. I got a 45 minute Mandolin lesson at no charge." — hokeyWB

Imagine the disappointment at realizing that that was not a euphemism and just being forced to play the intro to "Losing My Religion" for 45 minutes.

The Furry Conundrum

Unsplash | Patrick

"Dude kind of awkwardly leaned forward after some hours of talking and sort of half-whispered 'you're not... a furry... right?' He was incredibly relieved when I told him I wasn't." — valerianfox

This person never went out in a giant anthropomorphized wolf costume, really cleared up the confusion in the future.

Medical Advice

Unsplash | Ani Kolleshi

"'Do you know anything about hemorrhoids?' Kinda weird first date material." — IONenemabandit

I'm assuming that the person who wrote this must be a doctor or at least work in healthcare in some capacity, as why else would you risk asking this? Also, these two dated for 3 years after this, so maybe hemorrhoids aren't the worst topic for a first date... nah, actually, they really are.

Can I Bring My Bowling Ball?

Unsplash | Karla Rivera

"Met a girl one time to go bowling. Before she got in my car she asked me if it was okay if she brought her bowling ball. Little did I know that she was the state champ bowler 2 years in a row and I got my ass handed to me." — SirSnowlol

This one is actually quite wholesome, even if it must have been surprising going bowling with a state champion bowler. I thought I'd give you a bit of a wholesome one here, because hot damn, some of these are gonna get a lot worse from here.

The Weirdest Pizza Party

Unsplash | Alan Hardman

"I’m not sure if it counts as a date but we went and picked up pizza to bring back with us to his dorm. While we were in the restaurant waiting for our order, he seemed very eager to show me photos of his roommates and wanted me to rate them based on their appearances. I was thrown off a bit but whatever, I played along.

"On the walk back to campus he finally admitted why he was being so weird. He told his roommates I was open to having group sex and was trying to get me interested before I got to their dorm. I was very clearly not interested but he still asked after a few awkward minutes, 'So do you think you’d be down if it’s just 3 guys? They keep texting me asking.' I took the pizza from him and walked myself back to my dorm instead." — PotatoSaladMaster

This person went on to say that it was weird seeing the guy in class after that, which I can imagine!

Wildly Inappropriate Introduction

Unsplash | Sérgio Alves Santos

"A dude once asked me how many fingers I could fit inside myself within the first ten minutes of meeting up." — atikiin

And the prize for the most inappropriate introduction to date goes to... this absolute cretin.

"Pedophile People"

Unsplash | Jonathan J. Castellon

"I dated this ditzy blonde, She said 'you're like not one of those pedophile people are you?'" — TheMasterMekanik

Don't really see what her hair color has to do with this. However, the phrase "pedophile people" should never be said again, it's very unsettling.

Asking For Presents

Unsplash | George Beridze

"This was a few years ago but I once took a girl out who asked me to buy her an iPhone and when I laughed it off she told me she was serious. When I said no she asked if I would buy her a 12 pack of Mike’s Hard Lemonade and at this point, I was done. Turns out she lied about her age and was only 19. Took her home immediately and blocked her across the board." — godbullseye

Wow, they really set the bar high and then dropped quickly going from an iPhone to a 12 pack! This person did the right thing blocking her though.

Showing Pictures Of Their Mother

Unsplash | Leon Seibert

"Met a girl via online dating. Met up. Midway through coffee, she shows me her phone with a picture of an older lady on it. She asks me if I'd have sex with that woman in the right circumstances.

"Turns out the woman was her mother. She later explained that she wanted to make sure I'd 'still find her attractive when she's old and looks like her mom'." — reborngoat

I suppose I can see what she was trying to do there, but good lord that is a strangely intense way to broach the subject.

Arguing Over The Bill

Unsplash | Artem Beliaikin

"If I was gay... we were both dudes, same date he got really angry when I tried to split the bill and freaked out about how « he was the man », also lied about his age, so overall bad experience 0/10"

Wow, this guy sounds like an absolute delight. The person who wrote this went on to say that the other guy had a lot of "internalized homophobia", and that they actually felt quite bad for the other guy.

"Are You Like Chinese Or Something?"

Unsplash | Febiyan

"'Are you like Chinese or something?' She proceeded to insist that I must be Chinese for the next 15 minutes. I am, in fact not even a drop Asian." — square3121

I just don't even know what there is to say about this. Why would you be so insistent about something like this when you are wrong?

Asking Personal Information

Unsplash | Kari Shea

"I was born with cerebral palsy. It impacts only my legs and is relatively mild. I walk with a pretty pronounced limp, but otherwise I do alright. Used to work in a call center and became fast friends with this woman who worked on my team. Eventually, we went on a half-assed date because she was going to be moving across the country in a few weeks. We got talking about my disability and she just up and asks out of nowhere: 'What is sex like for you? Is it difficult?'

"I was just flabbergasted for a moment and laughed. I said: "Sex is no more difficult than anything else.'" — Theearthhasnoedges

Apparently these people still hooked up a few times before she left. And who says that true romance can't blossom at the workplace?

The Banana Problem

Unsplash | Lucian Alexe

"Gal saw a bunch of bananas I had in my kitchen and asked as she rolled her eyes if I ate those things?" — fishinspired

This is perhaps the most bizarre one on the thread. I mean, I just don't follow what is wrong with bananas? Even if you don't like them yourself, what else are people going to do with them?


Unsplash | Erik Mclean

"I got asked if I liked boggle. The guy then pulled out a boggle board and proceeded to solo boggle to show me how great he was at boggling." — bunkerbash

What is most shocking about this one, is that this person ended up marrying this boggle machine! They have been together for 14 years, and married for 10. They also own 7 boggle sets. I guess this is a legitimate dating technique.

20 Things You Shouldn't Talk About On A First Date

Unsplash | freestocks.org

"I went on a first date with a girl who looked up a list of 20 things you shouldn't talk about on a first date, and she went down the list asking me about each one of them (we both answered each question). So religion, political beliefs, past sexual experiences, emotional baggage, relationship with your parents.. you name it.

"We got married a couple of years back." — WigglyWeener

Thank goodness for another wholesome one! Ironic, yet wonderful, that that list managed to kick off a relationship that resulted in marriage!

"The Most Uncomfortable I’ve Ever Been"

Gage Walker | Unsplash

"This dude told me I had a good wife aura whatever the f*ck that means and then he asked me if I'd consider making him my husband. And it wasn't like a cute quirky joke or anything he was very serious and very odd and it’s probably the most uncomfortable I've ever been. This guy also tried to tell my severe allergies were all in my head." — Megling1285

I think you dodged a real bullet not marrying that guy on the spot!

Have you had a weirder first date? Let me know in the comments if so!

Grandma Energy

Unsplash | Cristian Newman

"'Do you mean to give off such a strong Grandma energy?' The guy I was out with asked me this when I was 22. But now I realize that I do give off a strong grandma energy and just lean into it." — nannerdooodle

It's good to know who you really are deep down! Even if that person is giving off "Grandma energy", whatever the hell that is?

Threatening Behavior

Unsplash | Blake Wisz

"What would you do if I stabbed you? while holding a 3-inch knife. This was right after this dude grabbed me between my legs (over my jeans) and said 'THIS Is mine'. Needless to say, there was no second date." — QuietShortGurl

This is absolutely unacceptable, and no one should have to hear or put up with this sort of harassment. The person who wrote this also went on to say that the guy turned out to be even more horrible than they could ever have imagined from their friends.

First Of All, This Is Definitely Not A Cult!

Allen Taylor | Unsplash

"I once went on a date that turned out to be a recruitment for a cult. So I guess being asked to join a cult would be the weird question." — mukino

This person said they met the girl on Tinder and she kept talking about a "group" she really wanted them to meet. They wrote that they should have seen the signs, but it was very apparent when they first met in person.