Should I give up or keep trying with this guy?

This boy approached me at the beginning of the school year (we are freshmen in college) and I was so mesmerized by him. We started having small talk and he asked for my phone number. He asked me to hangout a few times. He spent the night with me once, we hooked up. I have liked him so much ever since. He got into a fraternity, which demanded a lot of his time. We went two months without seeing each other. However, we have communicated with just small talk every day since he first approached me. Over thanksgiving break, I hooked up with another guy. I had no interest in this other guy, it was just a stupid drunken hookup. When I get back from break, the guy that I like asks to see me. We started hanging out a lot and I spent the night with him twice in one week (we had sex twice). We have such a great connection. I looked at his phone while he was sleeping (yes I know I should not be doing that) and I did not see conversations with any other girls. Then, one night when I am in his room hanging out with him he brings up that he knows I hooked up with this other person over break. I admitted that I did hookup with the other guy and that I do not like him or talk to him at all anymore. After that everything was fine and I spent the night again. Two days later he also sends me a picture of the two of them together while he is drunk. I was so annoyed because it is not fair that he can go 2 months without seeing me, then say stuff about me hanging out with other guys. I texted him “I am sorry I do not want you to think anything of what happened over break. We only hung out once and I have not talked to him since. I actually like you and do not want you to think badly of me.” All he said back was “its all good I thought it was funny thats why I sent the picture.” So there, I told him I liked him, and he did not say it back. Is this an obvious point that he is not interested in me? Is he just immature? Was the text not clear enough about my feelings for him? It really hurts because I like him so much but do not want to make myself look dumb and desperate if he really doesn't feel the same. I do not want to keep having false hope either. I’m just so confused at this point.

This guy is not interested, nor does he respect you. You have put yourself in booty call territory. It does not take two months to see someone, if you are remotely interested in them.

Treat yourself better. And, stop making your dates in men's bedrooms. You should be out on dates.

No, he's not interested. He is in it for the sex, but that's where it ends.

Let this one go.

too much chaos, let it go

Small talk and hooks up s lead to more small talk and hook ups. You have stumbled into a FWB without knowing and while you are wanting more from it, he is getting all that he needs from you.

If you don't want this, tell him that sex is off the table next time you hang out. He will then lay it on heavy, knowing that you like him, until you give in and give him what he is there for. If you keep resisting, you will be surprised how quickly the small talk and hook ups fade away.