What’s the most awkward date you have been on?

18 comments

1. I’ve been on a lot of awkward dates, but not because they did anything weird. We just didn’t click and were both too polite to pull the ripcord.

2. A double date I’ve been tricked into by a friend. I stayed for ten minutes out of politeness, but then I couldn’t stand it anymore and left, pretending I have to work.

3. Got catfished by a trans woman (fine, was Grindr anyway) she proceeded to tell me that she practices witchcraft (the dark one) fine i guess, but i laughed at her face..then proudly mentioning that she was not vaxxed. There i lost it..and of course got accused of being transphobic.

4. It was on a date that a friend set me up on with one of her friends and right from the beginning she seemed uninterested. We were sitting at a restaurant and I’d try to ask her questions and she’d give me yes or no answers, she had her face buried in her phone and it was just really awkward AF. I had planned on taking her to the movies and then to the bar afterwards but I just ate my food and decided to take her home instead because I wasn’t in the mood anymore. The funny thing was that as we got close to her house she actually asked me if I was taking her home and why because it was early, I just told her that I wasn’t feeling good and she told me to call her later and that was that.
   (A few days later my friend called me and asked me how the date went and how come I never called her friend back because she had been waiting for me to and all I told her was for her not to set me up with anyone again. And the weird thing is is that I had never seen this girl before but apparently she had seen me and she agreed to go out on the date so I don’t know why she was acting the way she was acting. And it’s a shame because she was really cute but I never saw her again after that but it is what it is).

5. She told me she wanted kids within the next 2 years. I was 21 at the time.

6. Oh man, this is painful just to recall.

   Back in high school, we were at a small kick back. 3 girls ask me and 2 of my friends to come back to one of their houses. No one is home- there is a hot tub, and there is beer. It’s a spur of the moment triple date- no other way to describe it.

   It starts out as fun- we play drunk hide and seek, we listen to music and talk . . . and then we chill in the hot tub and I show just what a little prude I am. One of the girls (who I thought was very cool and attractive) comes up to me and starts stroking my chest and I just ignore her completely. We go back in and both of my friends are kissing the other girls. What do I do? Kiss the girl who was clearly into me for around 3 seconds and awkwardly disengage . . . it was my first kiss too.

   She and her friends were rude to me all night. She then clearly had a threesome with one of my friends and one of her friends- I could hear them as I was sitting in the living room alone. The next day, she said “Your friend was amazing.” I said “Did you have a threesome?” and she looked angry and replied “You’re disgusting.” We hung out with them for a few more hours and they generally belittled me and made me feel like shit.

   I still don’t understand it. Were she and her friends mad at me because they thought I insulted the girl or was rude in some way? Awkward as fuck. Nothing I can recall matches it.

7. My first date with my current SO I sat back to back in a booth to my ex and her new SO. I made eye contact with her mom as I sat down. We were together for 3.5 years and this was the first time I’d seen her since we had broken up less than a year prior. I’m still with the girl I had the first date with but she thought it went horribly because I was panicking.

8. After a little talking and exchanging childhood info we found out that we were distantly related .

9. 29/2/2004.

10. We went to a movie that neither of us had seen. The movie was A Clockwork Orange.

11. A girl who looked beautiful in the pictures I’d seen of her, and was a friend of one of my closest friends years ago, connected with me over chat. She wanted some help with a short story she was working on and I worked as a writer before.

    We got talking and I’d heard of her from my friend, who had professed that he wanted to be with her but she was with someone else at that point and had just broken up.

    She got real flirty and even he was surprised at how much because he claimed she was not like that with other friends. I’m demisexual so it mattered lesser to me. I guess that’s why I came across as confident because I wasn’t really trying to impress her because I barely even knew her.

    She asked to meet me in person one day and I included my friend in it. She then said she had planned a date for just the two of us. I laughed it off and told her I’d just meet her as a friend. Either way, I knew her intentions and was willing to see where this went.

    Cue the moment she walks up to me, and my friend who was there as well since they wanted to meet, catch up over a cigarette like they used to in college, before the two of us continued to our lunch ‘to discuss the project’.

    She’s dressed in the brightest color of gold I have seen, and her face is an overcaked smattering of contrasting colors. Dark purple lipstick with red blush and gold glitter eye shadow. Bronzer all over every contour in her face. Dried powder bits on her neck. Too much blush and patches where foundation wasn’t applied properly. All in all, a face that doesn’t match the neck and arms in color.

    That gold outfit, was a saree gown. For a casual lunch meet. With sequins.

    The sight just left me stumped and I actually found myself finding a woman just plain repulsive, which I don’t do. I’m more of an indifferent kind of person in general.

    I shared a few smokes with the two of them and spoke the way I used to but every openly flirty sentence put me off further. I excused myself to the two of them, said I needed to leave and that’s what I did.

12. A girl who I worked with in a super market came up to the deli counter i worked out (while customers were there), and asked me on a date.

    She was good looking, and I admired her cojones for coming up in public and making the first move so I said yes.

    I soon after found out she’d asked out pretty much every other guy before me and been rejected, so I was last on her list.

    She picked the date – the movies (an honestly awful choice), and picked the movie, which was awful.
    She sat right down the front row (the worst place to sit imo), and kept trying to huddle into me, even though at this point I was very much not seeing a future.

    After that, I walked her back to where her parents were picking her up (doing the decent thing i thought).

    She waited UNTIL her parents came to kiss me.

    Awkward.

13. The meeting place was downtown so I reached Macy’s where she was shopping with her mom. After shopping was done we went to a diner inside of a food shopping terminal. The whole thing was somewhat awkward. She accidentally spilled ketchup on her pants and then began to freak out like “I want to go home and change” I set across and asked for seltzer water to help remove the stain after the diner we walked around for a little bit and then whatever excuse she used to go i was thankful.

14. She was literally a whole foot shorter than me, I’m about 5’11 so she must’ve been 4’11 or shorter. We were at a coffee shop and my friend saw me and thought I was out with my little sister. I don’t even have a sister.

15. I went on a date with a super religious girl. All she talked about was church and her church friends and her church groups. I’m agnostic on my optimistic days I suppose, but I couldn’t relate to someone any less than her.

16. Everything was perfect, from like 2pm to 8pm, after the dinner, she drops “yeah I’m probably going to move back to Italy soon anyway”… Ok then

17. I can think of a few:

    Got set up on a blind date by a female friend. Got the skinny on the girl who would be showing up, heard all sorts of great things about her, how smart, funny, etc she was so I was thinking “yeah, sounds good!” only to show up and find out that my friend was talking about herself and was shooting her shot. Pretty awkward as I had absolutely zero attraction toward her and was young enough that I hadn’t caught the signs of interest until I was slapped in the face with them.

    Met a girl at work (she was a customer) whose toddler ran up to me and basically wouldn’t let go, which was super cute and led to a conversation with the mom. I figured “hey, why not” when she asked if I wanted to go out. We went on a date and it was pretty good so I invited her to a group thing a few days later and she spent the night going to each of the girls in the group (most of whom had boyfriends who were there) telling them “He’s mine. Back off” so basically half of the group avoided me all night and I couldn’t figure out why. (one of the girls told me later what had happened…obviously I did not call this woman again)

    I sneezed a snot bubble the size of my head on a first date once.

    Girl and I both had…gastrointestinal issues…on a second date but were both trying to play it off cool so the amount of times we both excused ourselves from the table was comical. Made particularly funny because each of us only knew our side of it and had no idea what the other person was doing.

    I’m sure there are more, but those are the ones that pop to mind.

18. Girl said she was an organizer for a Republican PAC. Then asked if I wanted a blowjob. Politely declined and continued drinking my beer. I’m a socialist.