How do I figure out what he wants?

I would stop the sex right NOW! Tell him that although it was great and you are open to the idea of seeing if it could go somewhere your not willing to risk loosing such a special friendship for something so casual. Tell him that your at a point in your life now where your not willing to settle for less than whatever it is you want ie a relationship?

Tell him that it was special and your always wonder where it could of lead but that you are not willing to have casual sex with him anymore because your friendship with him is too special to gamble with.

If you really want to make him think about a relationship with you, as such a close friend you should know what qualities he would look for in a woman! ??

Perhaps you could bring it up in a fun and casual way one evening, ask him a few simple questions, these will really get him thinking about what he wants!

Q 1, What has he always wanted in a woman that he has not come across yet??

Q 2, What kind of woman does he respect??

Q 3, What are your weaknesses when it comes to women??

Q 4 How do you think your last girlfriend would describe you to her friends??

Ask him these questions in a cheeky and playful way and not only will they make him think about what he wants, your be surprised by the answers he gives and also become pretty unique in his eyes as these are questions any woman should ask a potential partner but 90% never bother to!

I hope this is of some use to you, let me know how it goes. Good luck.

He probably reached out to you cause he was feeling vulnerable. my thoughts would be that if you want to know what he is thinking, meet him in private set all the information out on the table, tell him how you feel and how you want things with or without him. All in all make sure you tell him what your friendship means to you and make sure that you leave nothing out there that can jeopardize it.

Good Luck!!