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I don't even know really what it is I fear in this case. What to do? What the hell do I do? I've never been on a date that wasn't a double-date that consisted of basically dinner and a movie. It'd be wonderful if I had these exciting original ideas to do with this girl, like involve her in my social activities I do with friends. Well I have almost none of that. I have very few friends that I would actually do anything with (my best friend just moved all the way to Las Vegas a couple weeks ago. I live in Ohio. I now have nothing and don't want her to get bored to death upon seeing I don't do sh-t in my spare time). This is why I can't picture myself actually being in a real relationship that lasts, because I'm scared to death about not living up to her expectations and then leaving me. It's absolutely debilitating.
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It's ok. I'm insecure as well. I had my heart ripped out, and I haven't ever really recovered from that. That doesn't mean you can't have a relationship. I was lucky enough to find someone who understands me and is willing to help mend some of the bottled up issues I have because of that relationship.
That was also my sense. That he's trying really hard. Maybe that's why it doesn't feel authentic. He's nervous.
I would stick with the internet thing as your "dating service" but would also try to meet women in other areas too. Your parents say that you don't have the best "filtering" skills, but I'm still weary of people that say "for the right amount of money we can fix your life and make you happy". I don't think that any external entity could really know me and figure out what I'm attracted to and need. For $50 I might try it, but definitely not $1,000.