For me, the biggest challenge is meeting women who I might find interesting. I'm a techie, and, for some reason, I've always got along great with techie women (or women in sciences or math). Maybe it's because they understand me better; I don't know.
Even though I live in San Francisco, it is hard to meet women who are attractive and with whom I can have a connection. IMO, OKCupid seems to be filled with the more "artsy" type women; nothing wrong with them at all, but I never seem to have a connection with them.
I think people pre-judge others too much. In older, much more traditional cultures, marriages managed to remain stable in cases where the bride and groom did not even meet until shortly before their wedding. That is a completely different topic though, but my point is that the set of people who you can live with happily and the set of people who you think you can live with happily probably do not overlap as much as we would like to think.
Expecting a connection at first is unreasonable too. Connections are built by shared experiences, not magical "love at first sight" moments. If you dismiss someone immediately, you'll never have a chance to share experiences.
I'm not saying that you should set the pass band on your filter to infinity, but the worst case scenario in talking to an artsy girl (or any other type of girl who you don't expect to forge a long term relationship with) is that you have a friendly conversation and learn a little.
At least, that's how it works for me. I've never dated a girl that was "my type". I have an idea of what I'd like in a girl, but for some reason I seem to meet (and enjoy being with) girls who don't fit that mold.
Even though I live in San Francisco, it is hard to meet women who are attractive and with whom I can have a connection. IMO, OKCupid seems to be filled with the more "artsy" type women; nothing wrong with them at all, but I never seem to have a connection with them.