Your Biggest/funniest screw-ups while playing the field.

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Or well, trying to XD. This can also include missed chances in retrospect and whatnot.

Lets see.... I have a few stories to perhaps show what I mean. So like yeah...

1) Way back during my senior year of highschool and even before then, this girl I really liked and myself got along pretty damn well. In retrospect, and of course with the rules of flirting and whatnot, she obviously was EXTREMELY into me (she being the touchy and clingy person she is, yeah).
Well, senior prom eventually comes around, I had no money and she actually offered to pay my pay in. Me being the fool I was back then said no because It wouldn't feel right if I didn't pay our way in. Well she found someone else and was even voted as prom queen. Alas she totally ignores me til this day other than the whole "hello/how was your day" type conversations. Yes, In retrospect, this is probably my own BIGGEST screw-up.

Now for the hilarious one, as well as it being the most recent.

2)Well, about a month or two ago, mt this girl from a different department from my work. Really good looking and whatnot (I fell in love with how her eyes light up when she smiles. We would talk whenever we saw each other, which wouldn't last long really since the nature of our jobs made it that way. We communicated more via flirts than anything, and we always tried to make the small conversations we had actually meaningful.
Well, last Thursday I was really having a bad day so she decided to try and give a bit of a comforting/cheering up type of smile to me when we ran into each other. Well, I tried to smile back and basically doubled over laughing. well, next day (last day I ended up seeing her, which was Friday), We ended up totally ignoring each other, dunno if it was out of anger/awkwardness/shyness on both of our parts or whatever, which is most likely I think considering the situation. So yeah, in the end all I end up feeling like a total a**hole because of it. Who knows, maybe we will be back on more or less speaking terms this week of work.

Gotta couple of not intentional ones! Once in a flat I was in one of the flatmates had some friends over and it got late and everything, I offered this girl who seemed nice enough but who I didn't know that she could sleep in my bed for the night. She thought about it for a bit, then politely declined, she seemed a little taken aback. Whereas what I was actually meant was I would sleep on the floor in the lounge and she could sleep in my bed, whereas to everyone else it sounded like I was just nonchalantly inviting her to sleep with me cos I didn't add any of that extra info in I was just thinking it! I worked this out after a few minutes and was really embarrassed

Another time I was in a pub and standing near a girl I didn't know but had spoken a few words to and someone went to get past so I went to gently move her by pushing on her hip, and somehow putting my hand in her privates Which she didn't seem to make any deal out of, and continued chatting but still..

My biggest screw up is usually telling other people I like someone instead of telling the person herself. It's an act of cowardliness and it makes me look like an idiot on my part yet I keep doing it. The monkey never learns.