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Embarrassing/Funny Dating Stories

Discussion in 'Chit Chat' started by warrior452, Dec 11, 2016.

  1. warrior452

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    What are some of your best embarrassing/funny stories about being on a date/with your significant other.

    I'll start: mine's technically not about dating, but...I was trying to check out a really adorable guy who worked in the grocery store. I was trying to get some donuts in the bakery section and still watch him on the dl while he was working (I'm a total creep, okay lol). I stood up to leave, and turned around, running into a bakery display, and almost sending around 10 cakes and a large sign to the ground. Fortunately, it didn't fall. He and his coworkers had a good laugh at my expense, and I walked away in horror. lol
     
  2. JonSomebody

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    My boyfriend and I had just started dating each other after being best friends for years and this one night after attending a dinner party. We were driving back to his place in the midst of a snowstorm. While driving...my boyfriend asked me to pull over to the park that was located in the area we were driving. I questioned him as to why he wanted me to pull over especially with a snowstorm taking place and he just grabbed me hand and said ..."Just do it please!". Once I drove to a designated area..he asked me to stop the car. He then jumped out of the car and went to the trunk where he pulled out some blankets etc. and entered the car through the passengers area...the backseat. From there he spread the blankets over the back seat and preceded to get totally naked and asked me to join him.

    My mouth dropped wide open as he kept persisting for me to do the same and join him in the backseat of the car and kept the car and heat going which I did. We preceded to have sex and the windows were all steamed up to say the least. All of a sudden...we heard a knock on the window and a voice asking for me if I was okay. I managed to let crack the window just a little and replied that we were fine. The voice was from a policeman and although he was happy to hear that we were okay..but he also informed me that we would have to move it along. After that...he said goodbye and as we heard his footsteps walking we both started laughing. Needless to say...the cop came back and knocked on the window again. This time he asked me to crack the window again for him which I did. What was really funny was that he had assumed that I was with my girlfriend or wife and his response just really had me cracking me up in tears. Once I cracked the window...he said..."Hey Buddy!..do me a favor...fuck that pussy good" and he started laughing and walked away. Me and my boyfriend was laughing out loud and then as I told my boyfriend to let us put our clothes back on...he replied.."You heard the cop...Fuck this pussy good"...haha...and I preceded to do so.

    After that..whenever I pass that park or in the vicinity of that area...I would get aroused thinking about that incident and just laugh to myself.
     
  3. Kodo

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    I have never been on a date, but one time I think someone was attempting to flirt with me. To which my response was and always shall be...

    [​IMG]
     
    #3 Kodo, Dec 11, 2016
    Last edited: Dec 11, 2016
  4. SemiCharmedLife

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    The first time I ever went over to the house of this guy I'd just started dating, he was grilling some veggies and asked me to bring the plate out to him. It jostled a little too much as I was walking down the stairs and I got veggies and marinade all over my jeans. We laughed about it, and later that night I ended up not wearing those pants :wink: . Two and a half years later, we're still together.
     
  5. AuroraBorealis

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    The only thing I can really think of, was when I was 14, I was very innocent, and had a girlfriend who was only a year older, but two grades ahead of me in school and one night I went out with her and her friends so I was an 8th grader hanging out with a bunch of sophomores and juniors, maybe a few seniors. The topic of "screamers" came up and I honestly had no clue what that was, so something gave me the idea to say "Oh yeah I love screamo" (I don't...and I didn't) my girlfriend and all of her friends died laughing..I still get really embarrassed when I think about it :icon_redf
     
  6. Linkmaste

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    This cute girl was checking me out and flirting with me and I absolutely had no idea at all. What's worse was that all my friends were dropping hints for me but I wasn't getting it lol.
     
  7. Lawrence

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    Yeah, OP, I cringed for you when I read your story :slight_smile:

    Many moons ago, I asked out an acquaintance at college and she walked away without responding

    I've got plenty more funny/awkward stories but that was one of the most annoying ever
     
  8. lovetoomuch

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    Well, this first date actually really happened and I feel bad because I decided to break it off.. but honestly, the date was hilarious.

    So the guy and I were texting for a decent amount of time. There was a running joke that eggplant (yes, you know the meaning) is his favorite fruit (I didn't even know eggplant was a fruit). Anyways, this joke went on and on until we finally met. So of course, I handed him an eggplant on the first date that I bought at a grocery store. My expectation would be for him to throw it out and just appreciate the gesture.

    Instead though, him being the outgoing one (I am shy as hell), he walked around the city carrying this eggplant. We got stares all night and it was honestly hilarious.

    We went to a gay bar and what capped the night was him having walking around with it there. Gay men obviously got the joke. But as we were leaving, he left the eggplant on the bar area. One of the bartenders ended up taking the eggplant and dancing around with it. A pretty damn funny night.
     
  9. tonymorning

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    can i ask a question here? what would you do if your old boyfriend invite you to hang out?
     
  10. RainbowGreen

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    I went with an ex friend in the old part of Quebec City, but I kind of forgot it was gay pride during that week. So, everyone thought we were dating xD (And that I was like 14 when I was 17)

    One group of girls even made us buy condoms from them (they were blocking our path). Then, when they went off, they said something like ''Those gay couples are starting so young nowadays!''

    It would have been a cool memory if the guy in question wasn't such an asshole.
     
  11. Linkmaste

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    Can this be some kind of short YouTube skit please? I would die from laughter.