1. The what-are-we conversation. Come on. He has twenty minutes to spare when you want to blow him, but he can’t take five minutes to define the relationship? If he won’t talk about what you are, then he clearly wants you to be his toy.
2. If you’re seeing other people. Even if he doesn’t have the guts to define the relationship, he should at least let you know if he’s sleeping with other people. If he is, but he doesn’t tell you, then he’s putting your health at risk.
3. Birth control. You shouldn’t hesitate to ask him to pick up a box of condoms. If he wants to get laid, then spending ten bucks is the least he can do.
4. Your period. It shouldn’t be embarrassing to tell someone you’ve been sleeping with that it’s your time of the month. He’s seen your vagina before. He knows the way vaginas work. So what’s the problem?
5. Who he’s going out with. Even if you’re in a FWB relationship, he shouldn’t lie to you. If you ask him what he’s doing, he shouldn’t dodge the question. He should be straight with you.
6. The STD conversation. Asking if he has herpes ruins the mood, but it’s something you need to know. If he hasn’t been tested recently, but he’s been sleeping around, then who knows how clean his junk really is.
7. What you want. If you’re comfortable fucking him, then you should be comfortable talking about fucking him. Tell him what you wish he’d do more of during sex and what you wish he’d never do again. You won’t get what you want unless you ask for it.
8. Who his exes are and what they’ve done together. It’s not a crime for you to wonder how many people he’s been with in the past. Or to wonder if he’s ever tried pegging or shower sex. In fact, it’s healthy to have conversations like that.
9. Who knows about your relationship. Has he told his friends about you? What about his parents? It doesn’t matter if you two are serious or if you’re just fooling around. It’s always important to know how much other people know, so you don’t accidentally spill info to them.
10. How he plans to act in public. Is he comfortable kissing you on the lips in front of other people? Or will he refuse to hold your hand once other people gather around? It’s best to know how he’s going to treat you ahead of time, so you don’t develop unrealistic expectations.
11. The where-is-this-going conversation. Maybe you know where you currently stand with him. But what’s going to happen in the future? Is he planning on leaving you as soon as he finds another woman to sleep with? Or is he planning on asking you to be his girlfriend, his roommate, his wife?