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Mixed signals - I need some advice, male perspective

So, here's the scoop I'm on an online dating site, met this guy we hit it off in the text. After a week or so of loooong messages I suggested we meet up, he agreed and we had a great bookstore/ cafe date swapped favorite titles and even picked up a book I recommended. During all this he tells me he's been on the site for a few months but I'm the first person that struck his interest so he's a tad wary about the whole thing, but the date had gone well and we agreed to meet up again.

A week passes we meet up again but this time it's awkward as f***, we're hitting up some art galleries with his roommates I fall asleep on the metro, get there late and then feel like a total third wheel because they're all art majors and super close and even though I appreciate art I can't drop artists names. Plus what the hell are you supposed to do in a gallery, appreciate the art and do your own thing, or insult the art not pay attention to it and just try and chat up your friend... and his roommates? Right loose loose situation. An hour later the galleries close we're waiting for a bus and he goes "You can go or come back with us." Then starts talking about plans later that night that he's going to hit up with his roommates. WTF? Is it just me or after a date goes well and you agree to go on a second date, at night on a Friday, don't you kinda leave your evening open or make plans that your date can tag along with? I know I do when I organize things but maybe that's just me. Anyways, bus comes I ask him if he wants me to leave or come with them -- doesn't answer suggests we get coffee and we leave the roommates. Okay maybe things are looking up? Now it's cold as crap and I wasn't really thinking earlier so I have on a jacket and a scarf which is fine if we keep moving but the coffee shop is full and we sit outside on metal chairs in 30 degree weather and I'm wearing tights fabulous. Conversation gets personal, but it's still just off -- like we're not hitting our stride. He asks me if I ever stop (working I suppose) and I say I do, I've stopped now. But I figure I've somehow struck him as not the right type and I consider the entire endeavor out the window. I'm freezing he suggests we part ways, walks me to the metro, then he says he's going to be in my neighborhood next weekend and we should hang out. Huh?

Didn't that date just flop on it's face? I got loads of NOT INTERESTED vibes, was awkward with the roomies, and failed your art test. Fabulous. This is just a sympathy bid, I'm non-commital and leave.

During the week he posts interesting articles and videos about things we talked about on my wall, I comment and do the same -- he never responds.

I just don't get it, I'd say he's not interested and leave it at that, but then he contacts me, or sets an open ended date, or just confuses me. He's a nice guy I'd like to hang out more, but I respect him and would be fine not going out too. I don't want to be the girl who can't get a hint, what does he want?
Updates:
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Also, I chose dating no idea why this got moved here. Other random info, I'm leaving the country in two months.
Mixed signals - I need some advice, male perspective
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