Most embarrassing moment on a date?

Most embarrassing moment on a date ?


Most Helpful Guy

  • I have a bad back from a childhood injury. Here's the story of my most embarrassing first date:

    I was working at Del Taco at the time and this very attractive customer became quite the regular. It got to the point where she would only come in when I was working and would always ask for me to take her order. She was tall, gorgeous and dark skinned. I was finally able to ask her out on a date.

    I asked her where she wanted to eat and she said Applebee's so we went there and gorged. During the dinner conversation I kind of lost track of what we were talking about and my mind wandered away from me but I hear her say..."but you probably don't know anything about my country... do you?" I stared blankly at her because I'd just assumed she was American. I hadn't heard a word of what she was talking about before she asked that question but she was fairly dark skinned. So I nervously asked "Africa?" She laughingly scoffed and said "I'm not African.." I gathered myself examining her features and color, trying to pick up on facial ques... "Mexico?" She laughed and said "No, I'm from El Salvador." I thought I had completely blown it. I probably sounded like such an ignorant white American jackass to her. Well, after dinner she invited me back to her place which amazed me.

    We're drinking a little, start kissing and fooling around, we get into bed and start taking our clothes off. She jokingly asks "You want top or do I need to show you how its done?" "No I got this haha." So I got on top and as things were starting to get super heavy and just before I actually inserted my fucking back goes out. I let out a scream and went completely limp. She screams and gets out of bed and turns on the lights. I'm on my hands and knees on her bed with a limp dick now blue-balling and I can't move because of my back. What does she do? She starts laughing at me as I ask her for help. She teases me a bit, then puts some clothes on, THEN she helps me gently out of her bed. She helps me put my clothes back on and walks me downstairs and helps me into my car. I slowly roll down the window and ask "Scale of 1-10, how horridly did I ruin my chances?" She leaned in through the car window and teasingly said "call me tomorrow, dinner is on me." and kissed me as I whimpered from the pain in my back.

    The next day she asked me to be her boyfriend. She called me her little old man since I was a few years older than her and my back went out while trying to have sex.

    We were together a year.

    • But that was one of the most embarrassing nights of my entire life!

Most Helpful Girl

  • I guess the most embarrassing thing was when I tried to wear high heels for our date at Rocky Horror and fell flat on my ass. But I fall a lot so it wasn't too awful :P Nothing he hasn't seen and mocked me for before.


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What Guys Said 1

  • Mine was when I got so nervous I didn't know what to talk about and we had many silent moments on the table in the restaurant.
    Later that night I was like "Omg you ******* idiot"


What Girls Said 1

  • Clumpy deodorant under my armpits with a sleeveless shirt. Never saw him again.