A crying sub is definitely hot. I've always been a sucker for tear-streaked makeup. That said, the first couple of times I make a particular person cry, it does create a little bit of anxiety in me, just because it's tough to be sure that they're crying for "good" reasons. If you back off and confirm that everything's fine, it can detract from moment a little bit, but I think that's a good time to be better safe than sorry. After everyone's gone through that particular situation a couple times and gotten familiar with it, I'm all for going full speed ahead...maybe with a little extra mascara for effect.