What is your biggest swing and a miss with someone you were interested in or even dating?

Like something either you said to them hitting on them or it can be something you tried while fooling around or during sex.
What is your biggest swing and a miss with someone you were interested in or even dating?
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Most Helpful Guys

  • Haha! I had a real dense one. I love jewelry and specifically giving said jewelry to a girl to enjoy more on her body. I have always found jewelry to be the sexiest lingerie (or make up… however you want to see it) a woman can wear and one day I went walking in to a small jewelry store in a small town and found an absolutely gorgeous collage girl behind the counter. As I sauntered through and asked her questions I was finding that she seem really nice and thought of jewelry the same way I did. When I finally told her that I wished I had a girlfriend to buy jewelry for she said that she wouldn’t mind a relationship like that…. And I froze. I had no idea how to respond.

    • Thanks for the MHO!

  • has to be when i was in college. we had to interview someone else from class, and I got this girl I had a HUGE crush on. In my list of interview questions, I snuck in the classic line "will you go out with me", knowing that she was going to read all the questions. But when she read that one, she only paused for a second, then completely ignored it and went on to the next. haha. Mhmmm, that was a big swing and a miss for me.

Most Helpful Girls

  • So i was trying to fix our relationship. It was anniversary of when we first met way back in HS. I spent 300 dollars on crab legs i shipped from MD. They arrived on our anniversary and i forgot to order them precooked and preseasoned with the special seasoning she liked.

    So they showed up uncooked/frozen and unseasoned. So epic failed. I tried to salvage them, but didn't work. And she was disappointed

    • Ooo ouch!

    • @Wish4UrB00ty it's when i knew there was no repairing us

    • That is a hard and important place to come to in that situation

  • I was fluttering with this guy in my AP English class my freshman year. My gay-dar did not go off at all. He was super cute. Rugged. We both loved Game of Thrones. He's gay... he's a big gay bear. DAMMIT!

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What Girls & Guys Said

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  • I had a co-worker who was younger but I thought she was receptive to dating an older man. I thought. . . but I was wrong. What I later learned about her indicates that I actually dodged a bullet with her rejection.

  • I was having meetups with this girl Lexi. Every evening we spent together was just simply amazing. But then some shit happened, i got mad and said some things i regret now. Now she's gone

    I think whenever i get mad i should just shut up, go home and take a nap

  • Bought her a navy blue velvet gown that she desperately liked and wanted and asked for. She dumped me several days later. I don't actually think there's causation/correlation between the two but in my mind they're connected.

    • Ouch!😳😬

    • @Guardian45 ... yeah...

  • The son of one of my former clients. Real sweetheart but he wasn't interested in dating someone godless

  • I went to a bar with a friend and we hung out for a while. there was this really pretty girl who was a waitress. I notices that she had an accent and I was able to guess where she came from. She was pretty amazed that I got it right, We left but I went back later by myself. I asked her if I could call her sometime and she just looked at me and said that she wished I wouldn't. It was pretty humiliating.

  • i've written 3 letters to women who didn't reciprocate their feelings. really poured my heart in them too.

    • Have you been reading my mail?

  • Not sure. I never invest time before approaching.

  • When i got down on one knee

  • Tried to date this Dominican girl. But she laughed in my face.. lol I thought it was a hilarious situation. Didn’t take offense by it. It is what it is. She missed out.

  • A girl was texting wanted me to send her a picture. When I did afterwards she blocked me without any reason 🫤

  • I don't know. Haven't tried that often I guess.

  • My biggest swing and a miss was when I was dating someone and tried to get her older sister into a 3some with us. EPIC FAIL! A few weeks later, my girlfriend dumped me!

    • Ooo ouch!

    • Easy come! Easy go!

  • How much time you got?😝

  • A few years ago, a coworker showed interest (I was attracted to her as well) and I did not respond (besides the company HR policy, I was married at the time and was not openly Poly).

    I wish I had a chance to respond to her after the divorce but she relocated to a different country and now is happily married!