Lizzie and Sam face a major crossroads in their friendship. Two new possible "depraved" disciples arrive on the scene: Sam's neighbor, Megan, and an old party pal, Jenna. Megan goes too far to please a date she met online. Jenna uses revenge sex to settle a score.
Jason tries to get Sam out of her Lizzie-less funk. Megan becomes a "bad girl" to snag a "bad boy." Jenna's ex begs forgiveness and she gives him one night to make him forget about all the women who came before her.
Sam makes a bet with her womanizing workmate, Dean. Jenna finds a sext on Ben's phone. Megan tries out The Rules of Depravity with a handsome client. Jason confronts Sam about her strange behavior.
Sam and Jason adjust to their new status post-breakup. Megan tries to stick to The Rules -- in particular, the one about not texting the morning after. Jason's boss, Rachel, is looking for someone to do a little "overtime." Sam tries a new hobby and meets a handsome new friend; and her brother, Charlie, pops in for a surprise visit.
Ben takes romance to another level for his and Jenna's 5-year anniversary. Sam and her new classmate have a night that leaves his apartment in shambles. Jason gets lucky with a new approach. Rachel learns that size doesn't matter. Meg deals with a flirty client. Tyler gets himself a sexy new bartender.
When Sam realizes she is the only one of the gang who has never kissed a girl, Amy decides to take her and the ladies out to the local lesbian bar. Dean teaches Charlie the 'guy code.' Charlie goes on the prowl and runs into Megan, while Jenna finds a big surprise at home.
Megan and Charlie give in to their mutual attraction -- several times -- despite Sam's disapproval. Sam enlists a pissed-off and single-again Jenna in a plan to bring Dean down while Ben asks Dean to keep Jenna occupied until he can win her back. Sam gets sage 'Rules' advice from Lizzie about Ryan., and Amy's hot one night stand shows up at The Bootleg.
Megan feels guilty about her hot new guy -- who isn't Charlie. Tyler needs a wife fast or he faces deportation, but first the gang needs to butch him up. Ben makes a confession and asks for Jenna's help. Jenna and Dean have started something they can't seem to stop, and Sam avoids defining her relationship with Ryan.
Megan has a steaming hot dream about Charlie, but keeps it secret. Sam attends a sex addicts meeting with Jenna and Ben and makes a new friend. Amy moves in with Carrie. Sam sets up Dean with a sex addict on a mission. Jason sees a different side of Rachel.
Sam wants closure through breakup sex with Jason. Charlies ex-girlfriend is back but Jason realizes he already knows her. Tyler and Pill Pusher Penni seek domestic bliss while Amy and Carrie deal with domestic stress. Rachel and Jason bond over closing a big deal.
Sam enlists Ryans help in spying on Jason. Jason and Rachel celebrate a business merger with a private merger. Megan meets a hot florist while planning Tylers wedding. Tyler and Penni have their immigration interview.
Sam goes all out to pursue Ryan. Jason gets his ice queen to melt. Sam helps Megan with the fine art of stalking. Jenna enlists Deans help in some sweet revenge.
Dean gives Megan some tips to boost her confidence. Ryan responds to Sams love letter. Dean asks Jenna out on a real date. A surprise wedding has some unexpected guests.