Whether you are looking to date someone or just have a play partner, there are some things that you really should discuss before you start ripping clothing off. They may be awkward to discuss but it important to get them out there. If you do not like their answer, or it doesn’t jive with you, you may want to reconsider if they are the right person to get down and dirty with.

Tested
When were they last tested for STDS? Have they had partners since then? Personally, I’ve never asked for proof of this from the doctor but I am sure some people have. Even if you are using condoms, if you are engaging in any type of oral sex, this is relevant. Unless you plan to use dental dams and other equipment to avoid direct contact.
Birth Control
Another important discussion. If neither of you has any plans to have children with each other, or at this time, birth control is a must. Never believe a guy who says he cannot have children (I know a lady whose guy told her this, guess what? she got pregnant). If he says he has a vasectomy, you may want to have a dr’s note before you agree to no condoms. Regardless, you should use them for the first while due to disease. I am a firm advocate of the woman being on some form of birth control as well. The form may be discussed as not all methods are as fool proof as others.
Pregnancy
What will happen if the female gets pregnant? This may not be a first night discussion but if you are going to remove a type of birth control (ie condoms) and only rely on one or none, it is likely a good discussion to have. Even if neither of you are looking to have children, accidents can happen and it doesn’t hurt to know the other person’s opinions before it happens.