I'm not sure which category to post this under, but it couldn't hurt to get a male perspective on this.
My boyfriend broke up with me two weeks ago (We're both 20). There were a few reasons, (drama with his best friends, his parents, some depression, stress about money/life) and he decided he needed to be alone for a while. We had only been together for a little while, so it was still a new relationship, which was more than he was able to handle along with everything else. Within the next few days, he initiated chats with me on facebook, looked at my dating profile a few times, texted me to see how I was....all of that. He has said several times that he still really likes me, he just doesn't know what he wants and wants to make sure he does before starting anything again. *Since this sounded like a cop-out to me (because seriously what does that even mean), I told him not to come back unless he's serious about it, he agreed that was fair, and he's been sticking to that, making it obvious that he knows that's what I want and wont go there until he can
The last time we talked, he asked if I didn't want to talk to him anymore, and I said that we could be friends later maybe. I didn't hear from him for a week after that. I assumed by this point that I would never hear from him again, at least as more than friends, and then yesterday he messages me saying he misses my voice and misses me in general. I asked how he's been and he said, "Awful, sick, and lonely." I ended up telling him he made his decision. He responded basically saying that he thought we could get back together if he gets his sh1t together. For some reason I didn't really answer that with anything other than reminding him that he said we should talk in a month, and it's only been two weeks. I could have pressed him for more info I guess, but I don't want to push him. I'd rather he take the initiative and do something, as he was the one that broke up with me. but now I just feel like he is starting to take initiative (it's not like him to say he misses me at all) and I'm just pushing him back. I don't want him to think there's no chance now.
The way we broke up was definitely left open for getting back together in the future, and was amiable. almost mutal. We both knew he wasn't being much of a boyfriend at the moment and it wasn't fair to me. While he says "awful sick and lonely" I know that a lot of the drama that was going on then is cleared up mostly. He and his roommate/best friend were at each others' throats at the time. And the money issues too are starting to work out. I mean, I didn't actually expect him to get stuff worked out, I sort of thought he was just losing interest in me when we broke up and didn't have the balls to tell me, but I'm starting to question that now. You would think he would drop contact if that were the case. It's not like we were long time friends before dating.
So what do you think? Does he actually miss me or is he just missing being in a relationship? I don't know if I should contact him first now, or let him, again, contact me. How do I balance making him work for it (ugh, that sounds horrible) and making sure he knows I'm still open to him? Why are men so confusing?