Ever been really nervous about asking someone about their sexual history and STIs, then ended up having a beautiful, completely unawkward conversation? Maybe not. And that's okay. I'd wager that for many of us there are few, if any, ideal moments to bring up contraception and sexually transmitted infections (STIs, more commonly known as STDs), but that doesn't mean it doesn't have to be done. Furthermore, no matter how sweet, open, and honest your partner is, you should never assume that s/he will volunteer information about sexual history or STIs, even if there's something you should know about.