Search Results: always end up in the friend-zone

I've been friends with a guy for 3 years. He's quiet with people he doesn't really know, but he's not like that with me and his close friends.

Freshman year, we got really close, and people assumed we were dating, but he'd always deflect/deny it. We were friends the next 2 years but not as close, but this year, we're close again. There's a fairer share of who texts first than before, and in class, he has chosen to stay sitting next to me when his friend moved somewhere else. He talks to me first more and uses my name in conversation. He has a snapchat and only has a few (all male) friends on it, and a few days I told him to add me. He did, then I made a joke and he pretended to be hurt and unfriended me. A few hours later he randomly added me back of his own will.

Yesterday, everyone was talking in class, and both of us ended up staring at each other for a few seconds. I laughed and he asked what was funny, and I said he looked at me so then I looked at him and neither of us said anything and I thought that was funny. He just kind of laughed/brushed it off. There have been several times when we walk through the hall together (although I initiate this) and other times where I feel like he may just want to make conversation with me; he'll ask obvious/unnecessary questions like why I'm carrying an umbrella (I'll call him out on it and he'll get jokingly mad/flustered). However, there are bad signs, like he doesn't always reply to my snaps, ~half of our convos are about school, and I can't pick out any definite flirting signs.

How can I tell if an overall quieter guy likes me or just wants to be friends with me? Should I test the waters to see how he feels?