Re: How to break off with old high school friends?
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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.
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This won't work. I had a couple of loser friends from high school that I'd outgrown after I'd gone to University and they never got the hint. The problem the OP's friend is that he has no basis of reference as to what constitutes a "real" friend, nor is he willing to abandon the friendship -- because the OP is the only friend he has.
The only way that I was able to ditch loser friends was to wait until the loser friend crossed me in some way and then escalating the situation (by getting really angry and refusing to listen to his apologies). Eventually the loser friend gives up on trying to salvage the friendship.
It's pretty immature, but it has worked for me.
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