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Whenever we hang out together to play videogames, it just feels so awkward. We don't tease eachother and make fun of eachother like people who are legitmate friends. We make smalltalk because silences would be awkward. We just talk about videogames or whatever, nothing beyond that scope.

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Well here's what I'd do, start teasing him more, like he's your friend. Also, talk about whatever's on your mind, be it your college classes, who you'd like to bone, what you think about God, whatever. If you aren't connecting, you will bore/annoy him enough to scare him away. Just keep rambling.

And if you are connecting, that's good right?