When Henry Beckman's girlfriend, Heather, convinces him to move to Chicago, his life takes a turn way, way down. She dumps him, he's out of a job, and into a new apartment - with a very outspoken roommate who has his own surreal opinions on life and women.
Henry's been living with Larry for two weeks and is a little exasperated that Larry has still not made room for any of Henry's stuff. He takes it upon himself to clean out a closet in his room and finds a mix CD of love songs. Since anything to do with love seems to be completely against Larry's nature, Henry badgers Amanda, Brad and Tina to fill him in on the significance of the CD, and shed some light on Larry's previous love life. Brad forbids Tina to spill the beans and she finds his new assertiveness hot, but Henry finally gets details out of them about Larry's one true love, Molly, who may have beaten Larry at his own game. Meanwhile, Amanda is concerned about the state of her private "area" when a doctor in her gynecologist's office cancels a date with her.
When Larry finds out that all his friends forgot his birthday except for Henry, whose disappointing present is an evening of camping he immediately sends them out to get him a real gift, one that doesnt involve mosquitoes and campfire sing-alongs. Amanda, trying to deal with being a horrible best friend, scrambles to find the perfect birthday present while Tina starts to realize that she may be keeping Brad on too short of a leash. Henry is determined to show Larry that camping is a fun, manly activity, but the women in his life keep getting in the way. Henrys ex, Heather, starts coming by when she realizes that blossoming can be a lonely process, and he manages to prove to Amanda that nobody can make their previous one-night stand as awkward as he can.
Henry reveals he still has the engagement ring he intended to give his ex-girlfriend Heather before she broke up with him. Larry pressures Henry to sell the ring online to pay for a wine refrigerator. Amanda borrows Henry's ring to impress a guy she used to date but hasn't seen in years. Meanwhile, the gang is surprised to find out that Tina popped the question to Brad, but has yet to receive a ring from him since they got engaged.
Henry starts to date Shauna, a barista from the local coffee shop. Ironically, Shauna is a girl Larry dated in the past, but Larry was forced to take extreme measures and lie about his sexuality in order to break it off with her. Despite Larrys warnings, Henry still wants to date Shauna, who obviously has boundary issues. When Henry runs out of options for getting rid of Shauna, he turns to Larry for his help, but after their attempts fail, its Tina who comes to Henrys rescue. Meanwhile, Amanda meets up with an old college friend who is determined to get her married off even if it means signing her up for the online dating service Last-shot-at-love.com. Offended by her friends suggestion, Amanda is determined to show her she can get a man on her own and goes to extreme measures to look amazing for an upcoming benefit her old college friends will be attending.
Tina is hosting Thanksgiving dinner, and Brad invites Larry, Henry and Amanda to join them, since Tina's mother Nanette and sister Alicia are in town for the holiday. Despite trying, Brad can't seem to make a good impression on Nanette, especially after Henry has to fend off Nanette's advances. Meanwhile, Larry mistakenly calls Alicia "Tina" during a make-out session, and Amanda gets very defensive about her femininity.