What’s the most awkward or disastrous date you’ve ever been on?

Question

Finchie40 · Accepted Answer

The one that comes to mind was when this cute blonde that hit on me first that I met at a concert , she was all over me and we were making out pretty much the whole concert , we exchange phone numbers and she ended up calling me the next day and asked me if I wanted to get together and go for some drinks and dinner at the bar restaurant , I said sure that sounds fun, I said I just have to wait until the tow truck guy comes and picks up my antique car that is going to the shop to get work done , so once he arrives and takes my car I will be free, and it won’t be to much longer because he is on his way now , she said she is already in the car driving so she said she can come to me so we can go together , I said that’s fine , shortly after I hung up with her
The tow truck pulled in to get my car as he was loading it on the trailer bed she pulled into my driveway way , I told her he is almost done so we can leave shortly , he was gone in 5 minutes too. So I said I can drive us and said your car is fine where it’s at. So we get into my car and I was making small talk with her in a respectful way , but she had this pissed off look on her face and I had no clue why, so I just ignored it and was still being respectful and polite to her , we sat at the bar together and I asked her what she would like to drink , and then I ordered us drinks , but she still had this pissed off look on her face , so I said is everything ok? And then she started going off on me and started saying some rude things , saying I was rude because my car wasn’t towed before she got to my house , I said you are joking right , I said I was having my car towed before you even called me , she said well you shouldn’t of had me come over until it was gone. I said you pulled in right after he arrived and it only took him 5 minutes, so I am sorry he wasn’t faster at it and didn’t think it was that big of a deal because I explained to you on the phone what was happening , so I shut my mouth after that and she pretty much ignored me the whole time , all I thought was this bitch is crazy so after i finished my beer I said let’s go , I said I don’t want to date someone that gets upset over things like this , that makes a big deal over nothing. So we got in my car and I drove her back to get her car and said I’m sorry having my car towed was the worst thing ever , and never talked to her again. It was the most awkward and disastrous date I ever been on lol

OlderAndWiser · Accepted Answer

Classic movie, in the same genre as Love, Actually.

When I was a 17 year old college sophomore, i did not date much - of course - because college girls wanted to date older guys and I was the youngest guy on campus. So one of my fraternity brother's girlfriends set me up with a blind date. I talked to her on the phone and we agreed to go see a movie. She selected the movie: Deliverance. NOT a good first date movie.

So I pick her up at her dorm and immediately observed the following.

A. She was not attractive. . . at all, and I am being charitable.

B. She walked with a limp.

C. She had very pronounced buck teeth.

D. Once the conversation began, I learned that she was a trumpet player.

All together, it was an unusual combination of factors and I felt no attraction to her whatsoever. We sit through the movie and I am so naive that there are parts I only understood later, and it felt embarrassing to be seeing such a movie with a girl.

As I was driving her back to her dorm, I was wondering. . . if she wants to kiss me, is there a way to do that where our mouths don't get locked together and I don't sustain grievous injuries. Fortunately, we ended the date with a hug and I never saw her again.

midnightmoon05 · Accepted Answer

Met online dating site… took sometime to meet up due to schedule conflicts…

when we met up, was at a very nice pier… towards the evening, he did not suggest any plans for coffee or restaurant instead… to walk towards a secluded construction site when getting darker… I turned and walked the opposite direction… that was that.

InStrictConfidence · Accepted Answer

1 coffee and 4 hrs. He drunk also only 1 coffee. He did not invite me at the end of the date. One guy told me what he stole from the work where he works.

AviatorTom · Answer

I've told this story many times.

Met this woman online and we agreed to meet at a Chinese restaurant. She was 30 minutes late, grossly obese, nothing like her profile picture. It was hot out and she wore this skimpy pink bra and shorts outfit that showed her folds of skin. Her first words when she saw me were "My pussy is so wet." I got up and immediately left.

exitseven · Answer

Freshman year in college I had a friend who was a commuter and he lived in the city. He and his girlfriend said that they knew somebody that they wanted me to meet. So on Friday night they picked me up at my dorm and we drove to a restaurant where she was going to meet us. She was already there and she was nice looking. I thought maybe this would be a good thing. While were were talking I told her that I was in Air Force ROTC and wanted to be a pilot. She was sort of a hippie and she thought that I wanted to bomb women and children. Thing just went downhill from there.

My friend thought it would be funny if he and his girlfriend left the two of us there. So they left. It took a while before we realized what had happened. She told me that she was leaving. I asked her if she would give me a ride back to my dorm. It would have been a 6 mile walk in the freezing cold and I was just wearing a jacket. She said no.

So as she was driving away I jumped on the hood of her car and grabbed onto the hood. She tried to shake me off and drove through the parking lot a few times but I had a good grip on the hood. Finally she stopped and let me in the car. We had a quiet ride back to my dorm. When we got there I thanked her for the ride. I did not ask for a second date.

ArrowheadSW · Answer

I met a lady at a wine event and she was friendly. We sort of "clicked" so we exchanged phone numbers and I kept in touch with her. I set up a date with her at a local restaurant. She showed up looking "long-faced" and she wasn't real communicative. She got a call on her cell phone which she promptly answered. Then shows up her friend who she was with the evening that I met her. Weird, but good thing since her friend was better company. Every time I tried to talk to the lady who was "supposed" to be my date, she reacted in a sort of grumpy way. Her friend seemed a bit embarrassed. I managed to finish up the conversation, and paid the bill and walked out with them. The next day I emailed her and asked if she felt OK, giving her a chance to explain herself. She responded in an email that had no capital letters or punctuation, and didn't really say anything. I'll put that one at or near the top of my worst dates. LOL

worldscolide · Answer

Years ago I went on a dinner date to a place called red beans and rice Cajun grill. It was good food. The only good thing about the date. We got there, we talked, she stayed on her phone the entire time.

No nothing dramatic happened. I paid for our meals and blocked her.

Another one was a weird one. She asked me to not only pay for her meal but her kids, who were at her home, and she wanted money for her baby sitter.

Again nothing dramatic. I paid for our meal, told her she should save some for her kids, and left. I blocked her.

But that's two bad ones. Out of dozens that were meh lol.

usernameobvious · Answer

Got stood up when she didn't show.  📱 Called her and she's like "I changed my mind"  I laughed it off after the call and it remains a funny memory ever since. 😅

Telekinetic-Potato · Answer

We met early for a movie. Walked around a mall. She was terrible at conversation.

Just no interests, unable to show interest in anything I brought up... Even just to help find some kind of momentum.

I think she felt catfished or something. Because she didn't even try to hold hands or share an arm rest.

We saw a decent movie and I just left her in the theater when the credits rolled.

I'll admit, I did kinda look stupid for a second because I forgot I don't have the AMC app anymore so I walked in thinking my movie would be free but I had to pay 😂 but if that's all it takes to throw you off... You're probably not gonna get treated very classy by me lol

Iron_Man · Answer

it was a blind date many many years ago and I had no idea what she looked like we met at night time. She was wearing shorts and she looked so different like she was from the ghetto and she acted ghetto then she started telling me to drive to the drugstore and I had a feeling I was being set up so I took her nearby and I dropped her off by the stop sign. I wanted to get out of there. I didn’t trust her. She called me on the phone later, but that was the most uncomfortable five minutes of a date I’ve ever experienced

AlperHan · Answer

It was probably when I met up with my ex-boyfriend and somehow also met his aunt 🙂 It felt more like a family get-together than a date.

MissSunshine2 · Answer

Once, when I was very young, I asked a man out who was meant to be a young man but looked to be on the bad side of his late forties or mid fifties.

Staximus · Answer

I met this girl I was talking to online at a bar around the corner from my house. Some band she loved was playing there. I said “wow, these guys are pretty terrible” and she was offended hahahaha. We didn’t talk much after that so I just left

dudeinohio · Answer

Woman who misrepresented her age. I dont date older women and she was older. Afterwards she invited me back to her place. I refused. She felt bad. I felt bad.

Anonymous · Answer

Everything was closed. I took a girl out the restaurant I had planned had closed for staffing reasons. The museum had closed most of the exhibits for renovations. The park wasn't closed but it started raining heavily.
I did not think she would want a second date.

Alex-Snow · Answer

We got into a political discussion which was a huge mistake. It ended abruptly.

AgentG111 · Answer

Oh hell not even sure how to rank them just bad.

BCRanger10 · Answer

When she brought a friend with her.

What’s the most awkward or disastrous date you’ve ever been on?

Most Helpful Opinions

What Girls & Guys Said

What's the most awkward date experience you've ever had? Can you share it?

What’s the most awkward or disastrous date you’ve ever been on?

Most Helpful Opinions

What Girls & Guys Said

What's the most awkward date experience you've ever had? Can you share it?

We're glad to see you liked this post.