I feel very awkward when it's only me and some other person (especially attractive men) walking on a street with a relatively far distance between us. There's no doubt that we will walk past each other, and it's always good to make eye contact (or at least try, on my part).

I feel odd because I don't know how far in advance to start looking at them. I hate doing it right when they pass me because I have to do a side glance like ">_>" which makes me feel kind of creepy or sheepish.

There are a lot of times when I wish I could start a conversation with a passer-by, and making eye contact would be a good start.