First dates are stressful enough as it is. They can end up as magical as a fairy tale or as torturous as a trip to the dentist. Between the expectations, nervousness and excitement, things usually end up rather awkward than fairy tale-ish.


“We were leaving the restaurant to go to a bar. We took separate cars. As he was pulling forward I back into his car. I had to pay for the damages. Now I’m engaged.”- Olga.

“So, I had asked this girl out who worked at Starbucks and I took her sleigh riding and when we were all alone in the middle of the snowy golf course there was one of those kind of awkward silences so, I tried to make small talk I said “”so have you heard about that serial killer on long island? Its crazy they haven’t caught him yet,”” and she gave me a look of terror. There were more dates in case you’re wondering but it didn’t work out. This all happened right around the time of that serial killer leaving the girls at Gilgo Beach.”- Thomas.

“I was about 15 and a friend wanted me to date her boyfriend’s brother.  Let me tell you he was not a good-looking thing, but me, the chubby 15 year old, agreed to the date.  May I also add he was older and drove.  So my date was driving around me town and it was kind of fun because my friend tagged alone. Well, at the end of the night, my date wanted a kiss so I am like ok just a peck on the lips, well this guy laid such a kiss on me tongue and all. That wasn’t the worst part. He had just eaten Doritos. Never again. The date was a nightmare, I don’t eat Doritos and the best is he lives in the apartment across the street from me now and I act like I don’t know him.” – Barbara.

awkward first date

“I went to Astoria to meet a guy for a date. We met at his apartment where he later told me he shared with his ex-girlfriend. We then proceeded to go out to dinner, where we ordered a shit ton of food. He ate everything basically, including my food, and then decided to tell me that he only had $10 on him. Then he had the nerve to ask me if I wanted tot go back to his apartment to drink and hang out with his friends. Yeah.” – Kristen.

Me: “Excuse me, have you ever had an awkward date you’d like to share with me?”

Ashley: “I’ve never been on a date.”

bad first date

“A friend introduced me to a guy who later asked me on a date. I agreed, told him I got out of work at 7 and needed to be home by 11:30 the latest because I had a 12 hours shift to work the next day. I didn’t think that was too much to ask. I called him when I got out at 7 and he told me he wouldn’t be ready until 9…he’s bald. It shouldn’t take him that long to get ready. Whatever. He picked me up at 9, he creepily already knew where I lived. He proceed to drive and drive and drive. I live on Long Island and soon started seeing the city. I asked him “”Where are we going. I have to be home by 11:3o. I thought I told you this.”” He told me he knew of a nice Italian restaurant in Williamsburg. After we got through miles of traffic, we sat down at 10. When I say this guy didn’t shut up, he didn’t shut the fuck up. He’d ask me a question and answered it for me. Let alone I was beginning to realize that he was literally obsessed with his dog. Ironically, one of his many stories was about an awkward first date he had. So, I realize my phone and iPad were both dead so I couldn’t play the emergency card and was stuck listening to him blab. He said “foods great right,” never let me answer though. The food actually sucked. He then proceed to take me to a “zombie tiki bar,” which is not my cup of tea to say the least. There, he continued to blah about his dog for another hour. On the drive home he took me on the “scenic route” home which took an extra 25 minutes to get home when he knew I was suppose to be in bed hours ago. I never called him back, but he still texts me eight months later.”- Ashley.

“I went on a date with a guy from okcupid who asked me to brush my teeth in the morning. He had an extra toothbrush in the package in his bathroom specifically for me.”- Lauren.

“First time I was out with a guy we ran into his ex that he was apparently still in love with and they kept chatting it up to the point where I got up and left the dinner table and went down the block to a bar to meet a friend. It got better when they finished dinner and strolled into the bar together holding hands. I guess you can call me the rekindler.” – Lisa.

I picked up my date and decided I’d take her to an awesome cozy Thai spot. As we pull into the parking lot she gets this nervous look on her face and starts acting funny. I asked if she wanted to go somewhere else, joked and asked if she had IBS or something. She says it’s ok. We sit down to eat, the waiter looks at her and almost breaks down talking about how he thought they were working things out and how could she do this to him and bring me there. I just said, “”it seems like you guys have some things to talk about, I’m gonna go.””Never saw her again.- Mandela. 

[featured image via CandyFlossMonkey]