21 Guys And Girls Reveal The Worst First Date They’ve Ever Had

By Rob Fee
1. Alex, 25

My date and I went to a little sushi place she picked, and she ordered an Arnold Palmer with her food. The waitress didn’t know what it was initially, and my date made a huge deal before irritatedly explaining that it’s half tea, half lemonade. She continued to be incredibly rude to the waitress — snarky remarks, smug attitude, really snappy. This went on for 15 minutes and eventually my date says to me, “This waitress sucks and is such a bitch, right?” Because she was so hot, I did the pushover, cowardly thing and was like, “Yeah, kind of.” Turns out the waitress was my date’s best friend and they were playing a prank on me, but she was so shocked that I agreed it was just awkward from that point on. Haven’t interacted since that night.


2. Genevieve, 24
I went to the movies with this guy I had never met, but we were set up by a mutual friend. I thought it was going fairly well, but then he went to the bathroom. I waited 5 minutes, then 10 minutes, then 20 minutes. He left. I had to call my friend to come pick me up and I never heard from him again. It was so humiliating.

3. Lauren, 32
I went to a standup comedy open mic with a guy who was performing for one of his first few times. He absolutely bombed. In his defense, several of the people did, but he was legitimately bummed afterwards and it was just the awkward thing that we avoided talking about for the next couple hours before going our separate ways.

4. Dominique, 27
A few years ago I went out with this girl I had met on OKCupid. She was already drunk when she showed up 45 minutes late. She was falling all over me and I knew we were about to get tossed out of the restaurant so I suggested we go to my house to order food. There was no way she could be in public. On the way to my place she kept saying she would have sex with me without a condom. There was just something about her stressing that I didn’t have to wear a condom that really creeped me out so I got her some water once we got to my place and called her a cab. It was a complete disaster.

5. Keith, 22
I decided to meet up with someone from Facebook, who claimed to be in my high school graduating class. She said she remembered seeing me and she was very pretty in her Facebook photos, so I couldn’t believe I was unable to recall her. When we met up she looked nothing like her photos. Even when we were talking on the phone trying to locate each other to meet up, I actually walked right past her unknowingly because she looked absolutely nothing like the pictures. I’m not trying to be shallow, but physically she had used angles to manipulate her appearance and it was almost offensive that she thought that it was okay to blatantly lie to people. I finished the date hastily and never spoke to her again.

6. Mallory, 21
I got set up on a blind date with my ex. It was through a friend that didn’t know we dated (and ended on terrible terms) so needless to say the date didn’t last long. I never tried another blind date again.

7. Michelle, 23
This guy who I met over Instagram asked to take me out several times and I resisted and declined several times, but one night I decided why not? We went to this really nice bar uptown, and enjoyed a variety of fancy cocktails and overpriced appetizer type trays. When the check comes he goes to pay, but his card was declined. He pulls out two more, both of those are declined as well. I had to intervene and save us some embarrassment, because I’m not sure what his solution would’ve been, but I didn’t want to roll up my sleeves and do dishes. I paid, and we agreed to a second date, but I joked with him to bring cash next time. He texts here and there but hasn’t mustered up the courage to ask me out again. Did I get conned into buying some dude expensive drinks?

8. Ally, 27
This wasn’t as much about the person I went on the date with as what we saw on the date. He was a nice enough guy, but during dinner at this cool, new sushi place I spotted a familiar face across the room. It was my dad and he was making out with a lady. The lady was not my mom. I was so horrified I ran out of the restaurant. My poor date was freaking out wondering what he did wrong. I asked him to take me home and explained, through tears, what I saw. I’m sure he was a good guy but after a first date like that, there was no future.

9. Don, 36
It was half date, half her trying to sign me up for her pyramid scheme.

10. John, 33
I had been talking to this girl for a few weeks and she finally asked if I wanted to get together on a Saturday afternoon. I happily agreed, even when she asked me to wear a suit. I figured it was odd, but thought we were going somewhere fancy, which I was excited about. We were not going anywhere fancy at all. We were going to her aunt’s funeral. She told me she needed someone with her but knew if she told me I would’ve said no. Obviously I would have liked a little heads up on it, so I spent our entire first date meeting her weeping relatives at a funeral.

11. Triston, 28
It was actually a good date at first, after dinner we went to her apartment but it turned out she had cats. We tried making out but I legitimately had to sneeze every 15 seconds. One of the sneezes caused a glob of allergy related fluids to shoot like a rocket from my nostrils and onto my upper lip area, and that was when every last bit of sexual tension disappeared.

12. Kelly, 26
I am a strict vegan and make it clear to any potential suitors before we ever go out. That didn’t stop this guy from taking me to a Mongolian BBQ restaurant for our first (and last) date. I ate crackers and salad while he feasted down on enough meat to feed a small town.

13. Chelsy, 31
We went for drinks but afterwards we were hungry and nothing was open… Except Denny’s. We ate Denny’s. I don’t know if it was the combination of alcohol and syrup soaked pancakes or what, but my body immediately responded by making me go to the restroom for what was at least a 15 minute absence, maybe longer. I destroyed a toilet and was gone for so long that there was really no way to play off what’d just happened behind the doors of that lady’s room.

14. Shana, 22
One time I thought I was going to watch football with some friends but it turned out the guy I was meeting was under the assumption we were on a date. I felt really bad because I have a girlfriend and I’m also not gay. We still watched the first half of the game but I made an excuse to leave because we were both quite uncomfortable.

15. David, 28
We met first at a Starbucks and while talking a group of loud teens sat at the table next to us and decided to talk a bunch of crap about things like what I was wearing, or how she was hot and they’d do this, or that to her. It was loud on purpose, so we could hear it and we pretended it wasn’t happening but I felt like such a chump not speaking up at any point.

16. Gia, 23
This guy tried to be really sweet and surprise me by taking me to a book signing by a well-known author because he knew I was a big reader. The problem was that the well-known author was my awful ex who cheated on me and nearly ruined my life. I didn’t want to be mean to my date so when we pulled up I told him I was really hungry and would rather go eat, because I didn’t want to get into the story. He got really upset and said I was unappreciative and he would rather just take me home. I was going to explain it, but he was being such a jerk at that point, I just chalked it up as a loss and moved on.

17. Nina, 27
It was actually a fantastic date until afterwards when I went to his place and he had pictures of himself with a woman all over the place. Like, clearly he was in a relationship, but he claimed they were old and that was his ex, he’d just not yet taken them down. I asked him to take me home within 10 minutes and he kept pleading otherwise but after a while I got angry and he still refused, so I wound up walking to a nearby shopping center and calling a cab to pick me up from there. He still likes my Instagram pictures sometimes even though I don’t follow or acknowledge him.

18. Lilliana, 25
A guy took me to see a marathon of the Hangover movies. He may have actually been the devil.

19. Zane, 21
I had talked to this girl for a while on social media and we agreed to meet at a mutual friend’s party. She appeared to be into me for two hours while we talked, isolated from the rest of the party. I went to the restroom, got a new drink, chatted with some other people for a bit, but afterwards I couldn’t find her. I didn’t see her the rest of the night, and nobody knew where she’d gone. As I was leaving the party, one of the many cars was an SUV with fogged up windows. I didn’t find out until the next morning through our mutual friend that it was her in the vehicle, and she’d banged some dude she had met only minutes after me.

20. Roman, 26
The girl I was really interested in asked if we could go apple picking, which is as boring as it sounds. I wouldn’t have minded boring but I was allergic to something there and my face swelled up like the Elephant Man. Imagine that scene out of Hitch, except I don’t have the charisma of Will Smith and there was no wacky sidekick. She never called me again, for some reason.

21. Jackson, 20
I started talking to this girl online, we got along well and agreed to meet up on a popular street that has a bunch of active nightlife, like restaurants and bars. Well I go to meet her at the place she chose, but it turns out it’s 21+ only. I’m texting her explaining that I’m 20 and can’t get in. After like 15 minutes she comes out, says hi and chats, then says she has to go back in because it’s one of her friends’ birthday, but she’d like me to wait for her to come back down. I waited another 20, at least, before saying screw it and calling it on what was the shortest, yet most humiliating date ever. 

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