@chobobot: Do it. Everything in life is a learning experience, a chance to learn more about yourself, and if you can approach dating that way too, you'll be fine. You open yourself up for rejection, but it's such an opportunity to put yourself, your wants and your needs in a perspective you may never have had the chance to see before.
I never went on a single proper date before the age of 27, myself. The very notion that I might be able to meet someone seemed, to me, crazy and unrealistic. The idea of even trying, kinda scary and weird. I had no self-confidence to speak of, and it didn't take much to make me anxious about anything remotely social. But I eventually got myself over many of my hurdles, and I'm on a good track. Even got myself a nice girlfriend on the way, go figure.
My getting over anxieties and hesitations has been an ongoing step-by-step process... working myself up to getting myself out in the world more, building my character through more interactions with folks. Wish I had a real solid answer that helped me flip my switches, but it was really just a progressive series of "I'ma do this" moments that occurred when I felt ready for them. Chatting up people more than I normally would. Accepting invitations to social events when normally my anxious nervousness would turn them down. Making friends and slowly becoming more outgoing with said friends. Working up the nerve to ask a girl out. I've found myself steadily being rewarded by life as I've begun to be less passive and more proactive -- which kinda sounds like dangerous advice to give, I guess, but that's my experience. It's still important to pace yourself and really have honest conversations with yourself, "am I ready to do this? Do I want to do this?"
Therapy's a good thing too. I started seeing a therapist recently, because even though my situation in life is vastly improved from before, the anxiety I suffer is still very real and I still will get attacks with the right combination of stressers hit. But therapy has helped with that immensely, and if there's one thing I could force my younger self to do, it'd be "go see a therapist." Fear, shame, and pride on some level, kept me from ever considering it an option before. But the therapist I'm seeing, she's really helped me to understand and contextualize how and why my brain works the way it does, and given me good tools to mitigate anxious episodes. She's also done a lot to boost my confidence, managing to instill in me that there's more roads open for me than I ever allowed myself to see before, and is helping me kick my latent mental habits that keep me down. I can't recommend it enough.
Rambled a bit there. Surely not all of that story is applicable to you, but I figured I'd share in case any of it is helpful to hear.
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