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

[Anonymous]

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.

[OlderAndWiser]

He started out having the hots for your roommate so that is a warning. At you age, many guys are too immature to know that they shouldn't talk about previous sexual partners with their new love interest. He may be broaching that topic so that he can discuss sex with you; perhaps he wants to see how you will respond.

Don't wait to see what will happen. The next time he is at your apartment, have a private discussion with him. It is okay to tell him that you have some interest in him but you can also lay out some ground rules, such as :

1. He needs to date you in a proper fashion and not just "hang out."
2. If he wants to date you, it is potential trouble to share a bed with him unless you are ready to have sex with him.
3. You need to let him know that, before you have any consideration of developing a physical relationship, you need to be in a monogamous, committed relationship.

These rules, of course, assume that you are wanting a committed, monogamous relationship. His reaction to those rules will probably tell you what you need to know.

[Asker]

The first time a joke was made about us having sex, I laid out the ground rule that I wouldn't have sex with someone I wasn't dating. Afterall, why buy the cow when you can have the milk for free? I'm not giving anyone the milk for free and I did at least make that very clear. He seems to respect that and always avoids doing anything that might make me uncomfortable. For example, when he wakes up with morning wood, he will either lay on his back until it's gone, or hide it with a pillow or blanket. On the subject of sharing my bed, I can agree it would seem inappropriate. Until my roommate gets her bed moved here, we actually share mine so when a friend stays, we typically let them sleep with us rather than alone on the couch... I wouldn't be letting him sleep in my bed at this point if we were alone, but with my roommate with us, I know there's no temptation for anything inappropriate at this stage to happen.

[Prince_teddy4u]

Wasting time. Can give chance but at your own risk.

[sHY-2V]

I would ask him up front what his intensions are. But tell him ur feelings to so he knows how u feel. Don't be afraid to accept the hard truth.