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1.
A contest undertaken among students of the Five Colleges in Western Massachusetts: UMass Amherst, Mt. Holyoke, Hampshire, Smith, and Amherst College. The objective is to become a Five College Champion. To do so, participants must get with another student from each of the Five Colleges under Easy, Medium, or Hard rules. Participants who complete the Five College Challenge on Hard difficulty may assume the title of Five College Master.

Easy: Any serious form of making out with at least one other student from each college or university.

Medium: See heavy petting. No sex necessary.

Hard: Sex with one student from each of the Five Colleges, no exceptions. For inexperienced pairs of Moho’s and Smithies the line between heavy petting and sex should be agreed upon beforehand.
Moho: Hey! You wanna take the five college challenge with me?

Amherst Guy: Haha sure but it wouldn’t be fair, I’ve already got one from Amherst on Hard

Moho: Oh don’t worry I just have Smith to go

Amherst Guy: Holy fuck
by Lord Jeffery Amherst October 06, 2010
 
2.
Having sex within one week with students from each of the five Claremont Colleges (Pomona, Scripps, Claremont McKenna, Harvey Mudd, and Pitzer). Unlike the somewhat similar Hampshire Five College Ch allege, there is no "easy, medium, or hard" classes in which to compete. As Yoda says, "Either do or not do; there is no try". Controversies over the fact that Scripps is all women placing them at a slight disadvantage and that fact the Mudders are possibly incapable of having sex.
Pitzoid: I'm one short of completing the Five College Challenge.

Mudder: I never met a Pitzoid that could count that high.
by dogman dave July 25, 2014