Charlie seeks his prison group's help when his partying ways result in him getting arrested.

Charlie asks for a second chance with the woman to whom he lost his virginity, and Lacey and Patrick try to keep up appearances when Lacey's parents pay a surprise visit.

Charlie convinces Jordan to pose as the fiance'e of a member of his prison group, and Lacey and Patrick gamble away part of Lacey's parents' money.

Jordan's twin sister, identical in every way except hair color and the addition of fake boobs, is in town. Jordan tells Charlie that the two don't get along ever since her sister slept with her former fiancee. She asks Charlie to help mend the damage between them, but he winds up sleeping with the twin. Elsewhere, Lacey's sister blackmails her into buying her whatever she wants in exchange for not revealing to their parents that the marriage to Patrick is a sham.

When Charlie's best party buddy becomes a priest; Charlie's tries to tempt him with women and liquor.

When Charlie tricks Lacey into believing her father is broke, she gets engaged to an obnoxious billionaire. Meanwhile Nolan makes a business arrangement with Sean's strip club.

Charlie's father sets him up with a hot, but quiet Catholic girl who turns out to be too wild, even for Charlie.

Charlie and Jordan hire a hot tie-breaker to work as their associate on the prison clinic program.