There's this weird fine line right before oversharing, a certain amount of time past the initial pleasantries on a first date where it's actually really awesome to bring up the serious things about yourself, and if done the right way breaks through the ice, inviting an actual sort of intimacy to exist and inviting the other person to actually tell you about themselves. Don't go too crazy though. You can kind of just say "fuck it" and be really honest. People will be surprised and you will usually get a second date.