Known her over 7 years. I'm massively into her despite, not being able to think of any reason why I should be, and have been unable to get over her, no matter how hard I try.
Shes fairly unatractive, and shes kind of annoying at times (well she used to be, shes chilled out a bit with age), but for whatever reason, I love talking to her, and enjoy being around her.
Well I don't know can't help you, that's not crazy about somebody
When your crazy about someone there are specific reasons either looks,mannerisms and personality, i say she's just a good friend that clicks with you
Ok so if your crazy about her what is wrong with her knowing that if she's crazy about you? It would be a warm welcome
The worst that could happen is if she don't feel the same way then it's just a knock to your pride and that's just a humbling experience that everybody should taste it doesn't do harm to a good personality
So I don't think asking twice is desperate
I believe with what you say that she was once crazy about you but it could have faded with your lack of presence and the fact that you have said in the past you could pass as a pimp, and also your doubtful negative thinking and you also saying you had loser acquaintances but only a handful of good friends, these things can put a person off a little or even hurt a person if their crazy about you
And I regret not seeing her more often. Even if it don't go anywhere, she is one of my favirote people to talk to. Hell, if she asks why I want to catch up, that would probally be what I would tell her, that I enjoy talking to her, and don't get to do it as often as I would like.
