Reddit, what was your worst or most awkward first date?

1. I was set up with a cousin on a blind date. First 5 minutes was spent trying to figure out where we had seen each other.
   — fitnerd21


2. I was 25 - met this older (40s) woman at a bar, very attractive and fun. Ended up taking her back to my place, great night. Decided it would be fun to hang out with her again, so we went out for a date at this bar. We ended up skipping out after a drink and go back to her place. Mid hanky panky on the living room couch, her 22 year old daughter walks in - I'd dated the girl for two months about a year ago. She very clearly recognizes me, screams and runs out of the room. Very awkward next 10 min as I gracefully try and exit the house.
   — Vaynar


3. Actually it was last night. We met through my roommate and went on a double date with him and his girlfriend, we had dinner alone before where she spent most of the time laughing to texts on her phone. We all decided to go the a bar nearby and once we got there we got drinks and she said she wanted to go see some friends from school who were there too. Well the next time I saw her she was leaving with another guy and I ended up third wheeling all night because I drove them there. This wench of a person texted me this morning saying she had fun at dinner and we should hangout again...
   — bingybongy1






4. My friends set me up on a date with an accountant. He bragged about how he was making a killing this tax season so we went to a higher end restuarant in town. We walked in, it's wicked busy and the hostess asks if we'd be okay in a small table or the larger booth. The guy says "The booth obviously" The waitress comes over in about 5 minutes and asks about our order. "Oh, I'll let you know when we're ready to order." I'm starting to get flustered, I was working as a nurse's assistant at the time and I was feeling mortified already when this happens. He waits five minutes, then he snaps his fingers and says "Waitress! I'm ready!" The entire dinner is a blur between his snarky remarks about the food, service and how dumb people are. At one point he tells me "I don't feel bad for people like that (the waitress) because their poor decisions got them here" The check comes and the guy asks to split the check (fine, I prefer it, especially when the date sucks) and refused to tip (I did, I gave the waitress a 20 and my sincere apologies) then he tried to invite himself into my apartment because he was tired and wanted to lay down. Hell No, Never Again.
   — chingu_not_gogi


5. Met this one chick on Tinder, a very attractive blonde who lived in the next city over. I was in the middle of a very dry spell, and she seemed to be interested. I'm stoked at this point, she is showing strong interest, and the conversation is going splendidly. The only tribulation in our conversations was when I had made a small joke saying something about acting autistic. Okay, no biggie, not everyone has my demented sense of humor. We continue to text and communicate back and forth for about a month and then decide to meet up. Sexual tension was high, and we'd both agreed to do something about it if at all possible. Well, I make the drive one Saturday to the city where she lives. We had agreed to meet at a diner not far into town. Upon getting to the diner, we exchanged an awkward side hug and got a table. The wait for the food was excruciating. In text, the conversation flowed very well. Here, not so much. The lack of conversation was apparent from both sides. My nerves were at an all time high, and I couldn't really eat a thing. I just kind of poked at my food, while she begins to eat - messily. She had ordered a chocolate waffle and proceeded to get chocolate all over her face and arms. I was baffled at how inefficiently this girl ate. Her fingers contorted and twisted in bizarre fashions to attempt a semblance of holding utensils. So, here we are, struggling to make even the most minuscule amounts of decent conversation when it dawns on me. This girl has autism - or at least some high functioning degree of it. Upon my realization, I now understand her odd expressions and lack of taking social cues. I immediately feel like the worst person on Earth for making an insensitive joke a few days before. As we moved on throughout the day, we spent it asking questions in a very interview-esque manner. She was a very sweet girl, and I did begin to enjoy my time. Towards the end of the day, I gave her a kiss and then started home. Slowly after the trainwreck that was that date, the communication began to cease.
   — trollmanjoe


6. It turns out that A Clockwork Orange isn’t a great first date movie. Knew I was fucked (or, um not unfortunately) from the very first scene of the movie.
   — isaacc7






7. I went on a first date a few weeks ago. We met on Bumble and hit it off and decided to meet up. He sent a message he was running late and he would be there in 10 minutes. I waited for 40 minutes and just when I started to put my coat on to leave he came in so I decided to just give it a go. He complained for an hour straight. About his job, his house, his roommate, his landlord, prices in Amsterdam, everything sucked. Every time I wanted to say something he talked over me. He then started talking about my body. How it is so sexy I'm so short and curvy, it made him feel so masculine. So sexy. He couldn't wait to see me naked. Those curves. So sexy. After the comments about my body he told me he thinks it's so sexy I have Turkish roots. So exotic. So sexy. He wondered if I was bilingual (I am half Turkish half Dutch, the date was in Amsterdam and I was speaking in English so yeah....) and when I told him i was trilingual he moaned???? 1,5 hours in I really wanted to leave so I told him I had some work left to do and that I really had to go. I got myself an Uber and we asked for the check. He told me he forgot his wallet and asked me if I could pay and he would pay me back. I payed and told him it wasn't a big deal. My Uber came 5 minutes later and when we walked outside he said "it was all a test". I asked him what was the test? He told me that he kept me waiting to see how long I would wait for him and he acted like an asshole to see how I would react. He forgot his wallet on purpose because he wanted to see if I wasn't a superficial stuck up bitch. He then told me I passed the test and he leaned in to kiss me. I couldn't really react because I was so confused so I didn't say anything and I dodged the kiss. The day after he called me to meet up again and I said that I felt we weren't a good match and I didn't think we should meet again. He then said "Ha, I knew you were a superficial stuck up bitch".
   — prinsesss


8. A few years ago, I met a super cute, super fit girl online who was working as a yoga instructor. I was so stoked she was interested in me, and we set a plan to meet ASAP. For our first date, I came to the gym where she worked to attend one of her intermediate yoga classes, followed by drinks. She was just as cute and charming in person, and I could tell we had great chemistry right away. Class starts, all is well. A few minutes into the class a small group enters late and proceeds to the back of the room to set up their mats. I was in the front row (trying to show off) and couldn't see what they were up to, but there was a lot of unrest and rustling. Soon they start complaining loudly about the class to one another - it's too crowded in here, why are we doing this pose, this isn't what I paid for, etc. The cute girl was doing an excellent job staying professional and ignoring them. Eventually, the complaints shifted to personal attacks towards her, apparently because they were being ignored - you're so stupid, there's no way you're a real teacher, what a bitch, etc. The group was loud and boisterous, and I could see the cute girl's composure starting to crack, so she suggested that they wait for the next yoga instructor to begin the following beginner's class which may better suit their style. Suddenly outraged by the suggestion, the group breaks up the class, approaches the instructor, and starts making all kinds of complaints and accusations that appeared ludacris from my perspective. Some people start walking out of the class, and confused regulars kind of still go through their yoga flow and I follow along, getting very concerned. By this time, the poor cute girl is full on crying because of the group's aggression. One of the group leaves the room and returns with a manager, who sees the disruption and disarray of the room, and an upset instructor. They take the girl outside for a chat, and she comes back in minutes later absolutely distraught. They fired her. The remaining regulars and I tried to reassure her and calm her down, but it was understandably useless. Still hopeful, I took her out for a drink afterward which ended up being pretty somber and forced. I didn't hear from her again. Bummer. tl;dr: Attended a yoga class with a super cute instructor, only to watch her get harassed and fired.
   — savvyleigh


9. Went on a double date with my best friend, her husband, and her husband’s coworker. The date starts off with him introducing himself and asking how old I am. I was 28 at the time and his follow up question was “what’s wrong with you, most women your age are married?!” Rude! But I stuck with it. We sit down for drinks and dinner. We all order things from the menu and this guy orders an “Odin’s Revenge” the server is confused and said they don’t serve that but they can make it if he tells them what to put in there. This guy rolls his eyes and speaks to the server in the rudest way. This is my dealbreaker but I continue to stick it out. The rest of the night was a barrage of assumptions he had made about my life based on social media, complaining about the service (which everyone else thought was good), and making remarks about how women age like milk and men are a fine wine and other red pill nonsense. My friends were embarrassed and really apologetic. Years later I still laugh thinking about how cringey the whole experience was. The date did provide my friends and I some great one liners and my friend’s husband promised to never set me up again.
   — waronkreesmas