Sup y'all, I've got a question regarding the notion of outcome independence in tandem with being forward and aggressively pursuing what you want.
A girl I was dating told me about another guy who she knew; the guy was clearly interested in her, but she felt indifferent and didn't think of him as more than a friend. They had some email conversations; the guy would invite her to coffee each message, but she would ignore/kind of pass over the request and respond to the rest of the email, hoping he would take the hint, but he continued asking her out (which she was just not interested in). I felt really sorry for this guy, man that must've sucked...
To give a bit of my own experience, I separated from this girl back in May, but over the summer we chatted a bit, and I tried to reconnect with her. I gave her an open invite once to an event, but she kind of did the same thing - ignored/didn't respond to the invitation, but replied to the other topics in the email conversation. I didn't want to be the guy in the story she told me that kept pestering her, so I pulled back and didn't invite her to an event again, taking things slower and more indirectly.
Later, she said she wanted to stop contact with me essentially because I didn't seem to hold the same interest in her as she did for me (though I did, probably more >_>. I feel that I was still showing interest and she might've overreacted a bit, but I do accept responsibility that I might've pulled back too far). In the end, I got burned and lost her because I didn't go after what I wanted with enough/more conviction; my guess is, I think she became a little dejected and left me because I didn't reciprocate her interest properly. Even when she mentioned that she was around my area for the day (in retrospect, a huge display of interest, I couldn't meet her though), I only indirectly offered to meet her at a public event I was going to a few days later - I imagine she thought I wasn't interested in seeing her. I don't think I have the chance to show her she was mistaken, as she doesn't want to talk to me >_>. Just trying to learn from the experience now ;_;
So my question is, how do you tread the line between the creepy guy that can't let go whom girls tell stories about to their friends, and the man who isn't afraid to go after what he wants and is detached from the outcome? How far can you push before you get into that territory? One thing is, it's SO much easier in person (where what words you say matter much less), but over e-communication this has become a problem for me.