Long question but I need some opinions. Is this guy into me or am I wasting my time?

Two years after a big break up I've finally come across a guy I actually think I'm pretty into. He's a close (friendzoned) friend of my roommate and he started coming over to hang out with us a few times since we moved into our new apartment, each time he has stayed over with us. The second time we stayed up long after my roommate went to bed and had a long discussion about, well, a lot, mostly pretty serious topics. When he left the next day, he hugged my roommate and I at the same time, one of us with each arm but he kissed me on the forehead.

The next time, all three of us slept in my bed with him in the middle and he did the same thing, he had an arm around both of us... Until later in the night when he slowly took back his other arm to hold me and do cute things like brush my hair behind my ear... In the morning he hugged me goodbye.

The most recent time, we had a discussion about our previous exes and what had happened with them while my roommate was gone and he was being pretty flirty with me in general even when she came home and even when the three of us went to the grocery store. That night was the same, we cuddled and somewhere in the middle of the night, he actually kissed me but with my roommate being there with us, I only allowed it to be brief. He left pretty early that morning and hugged me on his way out but that was it.

A big reason I doubt is that he's so open about previous conquests and really just sex in general. Not that I have a problem with that, but I doubt a guy would be likely to talk to a girl he likes about other girls he's had casual sex with (there are five). He makes jokes (my roommate assures me they're jokes) about wanting to sleep with me but he's not tried to push it to that limit. He even goes as far as to pull the blanket down in between us when he has a boner... Still, I am unsure if he's into me or just trying to get with me.
Long question but I need some opinions. Is this guy into me or am I wasting my time?
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