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The long term high school relation will generally fail after one or two years. However, this will put you in a better position than all those of your classmates who immediately got wifed with some upperclassman/entry mate within the first semester because you'll have much better friends. Regardless of who you're dating, don't ignore your friends for your relationship.
Long distance relationships can be troublesome, and some people would suggest that you avoid them at all costs. They generally only work when both parties are really committed to the relationship; they pretty much invariably don't work if you're more attracted to your S.O.'s hot body than to their witty banter.
If at all possible, avoid getting involved (whether in a relationship or simply a casual hook-up) with one of your entrymates ("entry incest") or, God forbid, someone in your a cappella group. Imagine spending two or three years having to sing cheerfully next to someone you went through a nasty breakup with, and you'll understand why. Unless you're really, really sure that that nasty breakup won't ever happen, it's probably not worth it. After all, as [[Joe McDonough '06]] once boldly claimed, it is ''possible'' to date outside your a cappella group.