I work on the staff of my school's newspaper. Last semester,

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I work on the staff of my school's newspaper. Last semester, almost all of our members graduated, save for me and another girl. So we had a whole new set of people come in. Most of them dropped out after the first month, so now we're about five people. One of the guys became my co-editor. When I first met him, I thought he was a pretentious dickhead and dreaded working with him. I only spoke to him if I had to.
But over the past several weeks, we've gotten to talking, even about non-paper related stuff. He's actually quite sweet; he even gave me a ride to class recently (I don't have a car) since we live 5 minutes from each other. He's in the Navy reserve and often tells me of his life since joining. Even though I didn't see it coming, I've fallen for him.
I don't have much luck with guys and tend to fall way too hard. With this guy, it seems different. I like that we're becoming friends first. At the same time, I want to see if there's something else. He graduates in December
and I graduate in May 2017. I don't know how or when to approach him without being weird. Any suggestions?
Pic unrelated.