Is he trying to make me jealous?

He's just curious and wants to know what will happen if he did. He won't do it trust me. Your over reacting.

Perhaps he is testing the waters? We have all grown up to believe that the only stupid question is one that is not asked.

Honestly though, without having a better understanding of your relationship it's hard to tell what he meant (he could be kidding, he could be serious).

Maybe just to see you're reaction! Why don't you ask him if he'd like a 3-some with her and watch his reaction! Might be fun!

Obviously he is thinking about it. Either that or he thinks that you would be into a three some. Trust your gut it's never wrong

Genesis5...we are friends with benefits. When I told him go ahead and have sex with her if that's what you want he then said "oh so you won't get mad?" I said no. Next night he said how about if I bring Danny over with me and Danny and my friend can get together...I said I thought you wanted to hook up with (my friend) her. He said no, me and you go to your room and they can have fun. He just sends me mixed signals all the time. Tired of playing his games.

Hello,
I'm not a guy but maybe he already had sex with your friend
and he wants to see your reaction before he tells you. If you're fine with it when he asks you he may tell you.

Good Luck.