If you don't mind my asking, FormerUnicorn, how are you meeting all these fun and interesting people?
The bottom line is that I'm willing to take a chance on the fact that I might not get along with someone.
I've been a member of OkCupid for six or seven years now, and I've used it primarily as a way to meet new people. The story was that I was living in England and I knew I was going to be moving to Alaska. I didn't want to arrive friendless, so I networked aggressively... and it worked so well that I had someone to go hiking with the night I got off the plane. And a standing thursday night scrabble game. And three offers for dinner and a movie.
I've probably met close to eighty people off of OKC in person. Some of them have been pretty scary (My senses are a bit better now) and some of them have just been plain weird. Some of them are obviously just looking for sex (not my cuppa tea). Most are nice enough people that I see a time or two and then drift away from.
That's not always the case. Some of the people I have met have been my friends for years. I even met my husband off of there, and we've been happily married for almost three years and together for almost six.
It can also be a gateway to other dynamics. A person I thought was my friend decided to terminate a friendship after he read my profile. I knew of Passport beforehand but we didn't really talk until I messaged her on OKC (boy am I ever glad I did!). I'm not sure I ever would have spoken to Local Guy had I been aware that I knew of him, but that connection took me completely by surprised, and it's one of the things that makes me smile every day these days.
Don't be afraid to strike up conversations with people. Ask coworkers to lunch. Neighbors, people at the library... just start talking to people, and be prepared to give your number out if you find someone who you'd like to talk to again! Good candidates are people who you strike up easy conversations with, or people you find yourself lingering for.
Don't be afraid to put yourself out there, cause the worst that could happen is that they could say no, or that they don't call! I'm still kicking myself in the pants for not doing this for: The awesome lady with the toddler in the jewelry section of the library in 2005, the sweet clerk in the jean jacket at bath and body works in 2006, and the artist at the art store in 2009, and the woman who helped me out at lowes when my car broke down last winter.
It can be challenging and it can be a lot of work, but it's always worth it in the end.