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I associate crying with sensitivity and vulnerability. From there, it's easy to associate them with weakness, but I think that's doing it a disservice. Sensitivity is a good thing. Opening up and letting what's going on inside out can be a remarkable experience for everyone involved. I think it's no surprise that crying is seen as a sign of weakness: our emotions do make us vulnerable, and it takes a certain degree of trust to share them with others. If you don't trust them, or if you expect them to take advantage of it (to make fun of you, etc.), then crying does become a sort of weakness.
I cry around my girlfriend and (rarely) my family, and my close friends. I'm pretty introverted, and I tend to keep things to myself. For me it's mostly about trust and understanding, not about weakness. I don't hide the fact that I cry; I just don't do it around others. For a while I had a hard time accepting this - I cried a lot as a kid, and I got made fun of it, and so for a long time I held back all of my emotions because I didn't want other people to make fun of me. Even now, when I know that won't happen, it's still hard to get out of those habits that I learned so long ago. It doesn't bother me, though. With anything as personal as that, I expect everyone to have their own approach to it, and mine works well enough for me.
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