Then there’s William Shepard Rose III (I only add that to let you know the level of pretension we are dealing with here, although there are two more pretentious men that we will get to shortly). He, of course, goes by Shep. Landon is infatuated with Shep because they went to college together and because Shep, as I am led to believe, is a successful a ladies man. He’s attractive in a “hot summer camp instructor” way; he hits on girls 10 years his junior and gets away with it because he doesn’t seem 36 at all. He has floppy hair and is quite tall, which means you can get away with murder in a place like South Carolina. He always is up to party and has a penchant for putting on a speedo when he’s drunk. (Landon and Shep should get married and have children and then move to the beach. Together, with both of their parents money, they can give their own family the world! And by the world, I mean Charleston.) He also has a protégée arrive this season, who is a younger, boozier, and blonder version of him. His name doesn't matter yet, but for some reason we do see a close-up of his bum in the episode within minutes of meeting him.