Tell us your most embarrassing dating experience?

Or maybe you never got to the date because of what happened before it?!


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Most Helpful Guy

  • About three years ago, before I was married, I had what I thought was a date with a Vietnamese woman. I picked her up at her family' restaurant but I flirted with her sister while waiting for her to get ready, and my date was so angry that she and her sister put me over their knees and my date spanked me with her hairbrush.

    Apparently this goes in in Vietnamese culture.so my date started with being spanked in her family's restaurant, then having to apologize, then having her discuss why I had deserved it.and instead of going out we ate in the restaurant, except that I had to eat standing up. The hairbrush really made an impression in more ways than one.

    .I could read the inscriptionn on the back of the brush imprinted on my seat when she was done teaching me and explaining the 'what for." She has a special brush she uses for this sort of 'date.;

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    • OK, I don't think anyone would ever be able to top getting spanked on a date....I'm amazed you would tell us this!!!

What Guys Said 4

  • I was so impressed with my date's older sister that I pinched her bottom while waiting for my date to get ready.the older sister got really mad and went off on me, wouldn't let her little sister go out on the date.

    Both of them were mad at me for months afterward.probably the older sister still is. God she was gorgeous though and so far out of reach, I couldn't help myself. Only 16 at the time.

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  • My first real crush was on a slightly older girl.She 17 when I was 15.She was not happy with my paying attention to her. She wouldn't go out with me but I still flirted with her. She got really embarrassed. Naturally she didn't want anything to do with a younger guy who couldn't drive on dates!

    One day she suddenly was smiling at me and made a date to play tennis.but when I got there she was there with a friend of hers, Marjorie a really athletic girl, blonde and busty,now in college, probably 20, She had graduated a year of two before.

    This girl was about my size. I rememberd her because she was the drum majorette before she graduated. She had the baton with her that she did her routine with.

    They took me into the field of tall weeds behind the tennis courts where the tall girl took me over her knees, and my crush pulled down my gym shorts. The drum majorettte spanked me silly with the baton she had brought , while my crush held my hands and bawled me out. She laughed at me and made fun of me when I started crying. She gave me a few whacks of her own when Marjorie was finally tired.

    Obviously the two had planned this whole trick.

    I don't know if I have ever quite totally recovered from this spanking, to be honest with you. I was so embarrassed and she told everyone about it.

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  • The most embarrassing date I've ever been on was a first date with this cute girl from my apartment complex. My ex-girlfriend saw us on our date at a restaurant and came over to the table to try to convince my date not to like me. She told her that I wear thong panties and asked her, "do you want to date a guy that wears panties and a skirt?"

    OK, the truth is that I do wear thong panties...pretty much everyday. That ex-girlfriend was the one who started me wearing panties because she said that I should obey her two rules of underwear; 1) go cute and 2) go skimpy. She actually threw away all of my guys undies (bikini) and replaced them with thong panties like 3 years earlier. Honestly, those panties are the most comfortable undies I've ever worn. Anyway, she started me wearing panties and was telling my date all about it. The fact that I wear panties, and thongs at that, is not something I would reveal on a first date. And the skirt comment was from a couple of halloween costume parties that we had went to together. I went as a cheerleader to those parties and, or course, wore a tiny skirt. But my ex-g/f loved that I went as a cheerleader when we were together.

    So...back to the date. She tells her these things and my date just smiles nervously. I was dumbfounded and just sat there with my mouth hanging wide open. It was so embarrassing. I then stand up to escort my ex-g/f away from our table and my ex-g/f twists my arm behind my back and pushes me down on all fours right in the restaurant. Then she sits on my shoulders and quickly reaches into the back of my jeans and gives me a wedgie. I was wearing a pink lace thong and she showed it to everyone. I was so shocked that I did not move. She just held my thong panty in wedgie position and said, "see, aren't those nice panties?" I could hear my date, and many others around us, starting to laugh. My ex-g/f stood up and marched off and I stood up and blushed. My date said, "you might wanna go the bathroom and straighten out that pink t-back." I nodded my head and went to the bathroom. When I came out of the bathroom, the waitress smiled at me and told me that my date was waiting outside for me. I walked out of the restaurant and my date said that she wanted to go home. She said, "I don't think we'll be going out again." When I dropped her off, she said, "thanks for an entertaining date and a very interesting story." I asked her if she'd be willing to keep the fact that I wear panties a secret. She said, "not likely, I'll probably tell as many people as possible." Then she closed the car door and walked off.

    That was the most embarrassing date I've ever had.

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  • I had a blind date a few months back. We talked over the phone before hand to get an idea of what we were getting ourselves into. It was a group of us. Anyways, the date was dinner and a comedian. Dinner went off just fine but the comedian was talking about relationships and blind dates. I thought it was funny. She did not. After the show she made up an excuse to leave and I never heard from her again. Oh well.

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What Girls Said 1

  • I started seeing this guy in high school who was an identical twin.I bet you know where this is going haha

    so we had been dating for about 2 months and one night they decided to play a trick on me. I went out to dinner with my actual boyfriend but after dinner he said he had to go to the toilet and so went out the back and his brother came in dressed in the same clothes and I had no idea. So we left and started walking and then I stopped and leaned in to kiss him and he burst into laughter and then my boyfriend came out from behind his car laughing. it was a horrible joke.

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