I'm lucky enough to say I've been in two meaningful relationships in my life, so I know I'm not a hopeless case when it comes to women. The caveat, though, is how I ended up in a relationship. The thing is, I'm not terribly smooth when it comes to asking girls out. The two times I had a girlfriend were both in college, and in those cases me and the girls grew closer over time until we just sort of fell into dating. Now that I am out of college I don't have that same stability of getting to know someone slowly but surely over time, but I have had such little experience and little luck asking someone out on the fly I feel very ill prepared the next time I want to try my luck dating.
I've been rejected before and that obviously hasn't deterred me, so my hang-up isn't really fear that the girl will say "no." Instead, when I'm interested in a young lady what happens is I get nervous I have nothing interesting to say or offer to our initial meeting, and I psych myself out. I have such a hard time making normal friends as is, I start convincing myself that my 5 minute convo with some cute girl couldn't possibly be entertaining enough to convince her to go on a date. My mind starts to blank, and suddenly I'm exactly where I feared I would be without anything to talk about, exciting or otherwise.
For several summers in a row I've been working with kids at camp, and I've been stuck in an awkward rut where I'm older than most counselors but younger than the higher-ups, so I don't have many people to socialize with. This year there is a young lady close to my age who I'm interested in as more than friends, and I take any opportunity I can to talk to her at work even if it's only a few passing minutes here and there. It's obvious she doesn't dislike me, but I'm having serious doubts if I'm interesting enough to be noticed as anything more than a coworker. At a staff party we talked several times and it went well, but the more nervous I got the more put off I was when she talked to other coworkers and it looked to me like they were hitting it off ten times better than I could muster. Keeping my eyes open from day to day, I can tell this girl is popular amongst the staff, and having my own social problems as is it's hard for me to imagine I'm interesting or personable enough to stand out as potential date material compared to my other male coworkers who can shoot the **** with ease.
I know if I keep doubting myself I'm never going to have the finesse to attract this girl or anyone else, but I don't know how to snap out of whatever it is keeping me back. I could, of course, just go for it and ask her out spontaneously rather than risk her getting close to another coworker in the meantime (assuming she isn't already taken or whatever), but I'm just so nervous messing up somehow, and just as I haven't worked through this problem yet I'm afraid I can't work through it in the future. I've been debating online dating as an alternative because then at least I know I'd be meeting people who are also looking for someone and might be more open to what I have to offer, but I don't feel like giving up in the real world just yet.