1. Have You Been Tested?
It might be awkward, but an awkward conversation is better than a lifetime with a disease. If he has an STD, you need to know before you decide to sleep with him.
2. Are You Seeing Anyone else?
You need to know if he considers you his girlfriend, or if he's sleeping with a handful of other girls. Don't assume that you two are serious. You need to ask.
3. Bad Hair Day, Huh?
This sounds like a ridiculous question, but there's a point to it. It's important to test him by teasing him a little bit. If he has "violent tendencies," then even a little jab like that will set him off. If he's dangerous to be around, you want to know from the start so you can get away.
4. Do You like Your Job?
This is a basic question, but you should know the basics about the man you're sleeping with. If he feels like a stranger, sex will be more awkward and uncomfortable.
5. What Are My Expectations?
Some of the questions shouldn't be directed at him. They should be directed at yourself. Ask yourself what you want from him. Figure out if you're only looking for sex, or if you want a real relationship.
6. Will I Be Okay if I Never See Him Again?
Here's another one to ask yourself. After all, some men will leave after they get what they want from you. If your man does that, will you be okay? If not, then you might want to hold off on having sex.