Well, it seems he's interested in pouring out in your guts (or the other way around), so it's almost the same, right?

Seems like he wants to stuff your guts back into you. It's going to be awkward to have a roommate who's into you, so to speak.

Take it in stride bro

At Microsoft (and I'm assuming some other companies), they teach MRI: 'Most Respectful Interpretation'. The idea is, you have no idea what stress someone may be under at home, or what traumatic event in their past may have triggered them, or whether they were thinking about something else with 90% of their brain and said something that didn't accurately reflect what they really meant, or if they're having a bad day, or whatever. So when you're upset or angry over something someone has said or written, you take a deep breath, and try to figure out what the person could have meant, that isn't offensive or hurtful to you, and you go with that. If it happens again, then you need to talk to the person; maybe they have Aspberger's or are somewhere on the Autism spectrum, or maybe they're being coached to be more direct and are having a hard time doing that in a 'soft' way, or whatever. If that's not it, and it happens again, then you're past the MRI stage, and you need to figure out how to work with the person. It's actually really useful. In this case, I can imagine motives your roommate might have had besides just being callous towards your pain; maybe what he himself needed when he was dealing with his emotional baggage was to feel attractive and 'normal', and he instinctively reacted to your pain with what he wished he would have received. Maybe it was a clumsy way of trying to accelerate the process of being close to you, because he associates 'dealing with unsupportive parents' with 'your partner supporting you'. And so on. If you're roommates, you'll have plenty more chances for him to show you how empathetic or indifferent he is; until you've got a few more examples, I'd start with the assumption that he meant well.