Funny Date Stories

First dates are infamously known for being the absolute worst. Sometimes the second or third ones are better, and sometimes they’re…not?

I went back on some of my Tinder messages and asked around to find out some of the most awkward date experiences my friends have been through.


We went on a really nice date, but I really wasn’t feeling it, so I planned on never talking to him again. He asked if I wanted a ride home and I said ok because it beat taking the bus. He pulls up to my house and I planned to hop out and say bye, but instead he parked at the same time my roommate was pulling in. Thinking I had already invited him in, my roommate brought him into our house, and he ended up staying for about 3 hours even though I didn’t actually like him or know what to talk to him about.


I went on a Tinder date but didn’t really like the guy, so I ghosted him. 3 months later he started dating my roommate.


I went on a Tinder date with a boy from another school my sophomore year of college. Things were going well, but then about a half hour into the date he asked me, “Would you rather fight one horse sized duck or 100 duck sized horses?” To which I replied, “100 duck sized horses...I guess!” He took a moment to take in this information, as his previously positive energy quickly changed to absolute rage. He started yelling, right outside of City Hall, about how that was the absolute wrong answer and gave me a million reasons why I was wrong. I walked away to catch an Uber, but he caught up to me and tried to…kiss me…?


He took me to see the LEGO movie, but I fell asleep and when he woke me up, he was yelling about how it was the greatest movie of all time.


I was on a Tinder date and he offered me a ride home. We got to where his car was supposedly parked, but there was nothing there due to the fact he had parked in a no parking zone, next to a fire hydrant, and also didn’t pay the meter. He got towed. Turns out he also only had a flip phone and was not even from the city, so if I hadn’t accepted the ride, he would have been completely stranded.


I had a nice date but wasn’t really feeling it, so I decided to text him and be nice and not just ghost him. When I said how I was feeling, he responded with “but I think we’re both very deserving of some sexy naked time”.


4 hours of Bruce Lee movies and no sex.


My friend and I went on a double date with these two guys we met at a club. We had a nice dinner but my friend wanted to leave, so we made up an excuse. While they were driving us home and we were in the backseat, my friend texted me “let’s go to the club” I said ok and we had the guys drop us off where we said was near our house. Once they drove away, we walked in the other direction towards the club, very proud of ourselves for skipping out on the date and excited to go drink. Halfway to the club we hear people shouting out their car window, we turn around and see the guys driving by and they shouted, “where are you going?!” Scared, we ran into an ally and walked to the bar through the back roads.


I was on Tinder when I was 18, I was in college and I matched with an 18-year-old in high school. He drove 2 hours to pick me up and drove me to his house, where he lived with his mom on his back porch.


I was with this older guy and thought it was so cool that I was with a college guy when I was a senior in college. He still lived at home though and therefore had to follow his parents’ rules. His dad was strict and didn’t like him to have people over when he was alone, especially girls. One time he asked me to come over when he thought his dad would be out, but when I was there his dad came home and I had to hide. I ended up hiding in his 9-year-old brother’s closet for 2 hours until he convinced his dad to leave for something so I could get out of the house.


He put Chicken Little on while we had sex.


A guy invited me to hang out at his house and smoke, and I was so nervous that I thought smoking more would make me less awkward. I smoked too much though and ended up projectile vomiting for hours all over his lawn. I don’t think I’ve ever puked that much in my life. I had to ask the Uber driver to pull over while driving me home so I could puke more.


I met the guy’s parents 1 week after I met him.


I was on a nice date but this couple in front of us at the bar kept slapping each other’s asses and made the vibe really weird.



And finally, after all these award, uncomfortable situations, here’s one story to make your heart melt this Valentine’s Day!


I was on a solo one-night escapade to Zurich during the opening of their Christmas markets. I headed out to explore, and my first stop was a little mulled wine stand at the market. The guy selling it started chatting me up and I stood there for 20 minutes while the wine “wasn’t ready yet” until eventually he gave it to me free with his number. That night after he got off his shift, he called me, and we met up for him to show me around Zurich a bit. He then offered to show me his small hometown in the Swiss countryside and said I could sleepover. I was now fully living a Hallmark movie; ditching the big city and my female empowerment solo trip for the small-town winemaker. Like all good Hallmark movies, we got back to his place and talked, and at this point he hadn’t even tried to kiss me, so I am under the assumption I’m sleeping on a couch. He then asked me, “do you want the inside or outside of my bed” and I was like “uh,” but honey...I was in too deep to say no. But it’s innocent, and we fell asleep in his bed, until I woke up in the middle of the night to being aggressively spooned and snuggled like I have never been snuggled so much in my damn life. The snuggling went on...all night long... until morning came, and he bought me a coffee, took me to the train station, and I never saw the Swiss Snuggler again.