"Friend, if you keep making scott pilgrimages, that girl with the squiggly hair will never talk to you. Mostly because she can't enter the men's restroom."
A relationship in which a great journey involving many social obstacles (exes, family, etc) must be taken before it can be initiated.
Person 1: God damn, being with Rebecca's such a scott pilgrimage; I've had to go through her parents and 3 of her exes and we haven't even kissed!
Person 2: Aw shit dude I'm so sorry