If a man does these things should a woman ever sleep with him?

He's playing games and trying to take advantage of you. The fact that you're posing this question to the open forum of the Internet, obviously means you have doubts about wanting to be intimate with him. The question you need to ask yourself is, (uming you are both consenting adults), whether or not you want the to have a deeper emotional connection, which it appears to me as if you do. If you do, then you should not only not sleep with him, but cut off your friendship as well. He obviously doesn't respect you and is more concerned with your perception of him through these little nuances and games. If it is love you're looking for, you surely won't find it here until this man decides to grow up and become a man. If it's just something casual you seek, then don't allow yourself to become emotionally attached.