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First and last one night stand!

Good for you Dan for having the courage to ask! Please don't assume that there's something wrong with you or that you did wrong that's the reason she said no. Your mutual friend said she just broke up with someone and wasn't ready to start dating again. There can be a million reasons she said no, none of which may have anything to do with you. She probably felt bad letting you down is the reason it took her so long, which shows she cares about you even if not in the way you hoped.
Don't give up. The next one may be the one!
Best of luck!
It did take a lot of courage for me. Ive never done it before. I think of myself as brave in most circumstances. Like i dont get scared of anything, i have no phobias. But speaking to and approaching females frightens the be-jesus out of me. Its unknown territory and i dont understand it all. One of my co workers talks to girls all the time and has no problem with It. He's like Joey from freinds. But for me it feels unnatural like my brain isnt designed for it. I wish it wasnt so hard for me.
 
It did take a lot of courage for me. Ive never done it before. I think of myself as brave in most circumstances. Like i dont get scared of anything, i have no phobias. But speaking to and approaching females frightens the be-jesus out of me. Its unknown territory and i dont understand it all. One of my co workers talks to girls all the time and has no problem with It. He's like Joey from freinds. But for me it feels unnatural like my brain isnt designed for it. I wish it wasnt so hard for me.

practice, practice. practice! Do it with girls you only want to be friends with so there's not so much invested. Just be nice and don't take advantage of them or mislead them.
 
It did take a lot of courage for me. Ive never done it before. I think of myself as brave in most circumstances. Like i dont get scared of anything, i have no phobias. But speaking to and approaching females frightens the be-jesus out of me. Its unknown territory and i dont understand it all. One of my co workers talks to girls all the time and has no problem with It. He's like Joey from freinds. But for me it feels unnatural like my brain isnt designed for it. I wish it wasnt so hard for me.
Unfortunately what comes naturally to others, doesn't always come naturally to us. However like everything in life the more you do it, the more natural it becomes. The first time is always the hardest.
 
It did take a lot of courage for me. Ive never done it before. I think of myself as brave in most circumstances. Like i dont get scared of anything, i have no phobias. But speaking to and approaching females frightens the be-jesus out of me. Its unknown territory and i dont understand it all. One of my co workers talks to girls all the time and has no problem with It. He's like Joey from freinds. But for me it feels unnatural like my brain isnt designed for it. I wish it wasnt so hard for me.
I used to be the same and it took literally years to pluck up the courage to say anything to someone I liked and the first time I was rejected too which really hurt and knocked me back at the time, but breaking through the fear barrier on the very first occasion is probably the most important step of all and it's a real breakthrough, now I know you'll be-able to respond to the next opportunity rather than wasting it which I did on so many occasions when I was younger. In fact there was even a couple of occasions when I really liked a girl who was blatantly chasing me so there was barely even any risk of rejection, but I was still unable to respond which absolutely killed me inside when I wanted to tell her how I felt so much, I'd even plan what I wanted to say beforehand and often the night before, but instead I'd just freeze up every time and sometimes the fear would even make me walk away while ignoring her making it appear that I had no interest in her what-so-ever. It's unlikely to ever be exactly easy, but it will get easier and even though you might feel a bit s**ty now it honestly will pass and you should be proud of yourself.
 
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