Dating Stories

Share your awesome or awful dating stories here. Let us know whether they were first dates, last dates, blind dates or fresh dates.

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  1. Jen says:

    Okay I will pick my worst of all. I started dating a guy I met at the farmers market. He was beautiful, like a ralph lauren model, tall, in nice shape, tan and longer hair. I thought he was a great catch, he owned his own construction company, had a nice home, yada yada yada. He was always so nice and complimented me often about my clothes and hair. I mean most men rarely acknowledge a womans attempts to look nice. After a few dates I thought he was a great catch. I never kissed him or anything… thank goodness. After our last date, he said he had the courage to do something he has never done before. He reached into a closet and pulled out a box, there right before my eyes was my date dressed up as woman in picture after picture. Oh the image is forever burnt into my corneas! He said he liked to dress as woman and it made him feel right. Beads of sweat started to linger on me due to fear. I tried to hide my horror, for he had to drive me home. Looking back everything started to click, the long hair, the compliments on my clothes. He wanted to wear them! He drove me home and that was that. My friends bring it up to tease me from time to time.

  2. frumgoth says:

    Can we include an awful pnone call that thankfully did not lead to a date? If not, you can delete this of course.
    A guy that was interested in dating me called and it started out as a nice chat. Then the conversation went really wrong as he asked “Are you into being dominated?” I was like, “excuse me? What did you say?” He replied, “You know, nothing major, just a little slapping around and hair pulling”. Keep in mind – we had not yet met in person! I answered “Well, can we go have a cup of coffee first?” then proceeded to never speak to him again!

    • batya from NJ says:

      what a loser with a capital L, FG!!! like you really wanted to meet him after that conversation, though-lol!! i know what i would’ve done with the hot coffee had i met him after that chat ;)!

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