Henry's girlfriend breaks up with him right after she convinces him to move to Chicago. With nowhere to turn, he responds to an ad placed in the paper by Larry Cone for a roommate, and he helps Henry begin his life anew.
Henry finds an old Mix CD stuffed in the back of Larry's closet. The questions he rises about the CD unravels an old relationship Larry had years ago. Amanda dates a gynecologist, who, after an appointment with her, suspiciously cancels their date that night.
Henry puts his engagement ring for sale on eBay. Then Amanda wants to borrow it to hurt an ex by pretending to be in a relationship. Heather returns, wanting to give Henry another try. Tina kicks Brad out because he hasn't given her a ring.
Amanda meets her college friend Lucy, who points out that Amanda's the only one in their former clique still single. So Lucy pushes Amanda into online dating. Henry asks a coffee shop girl out despite the others' claim that she's a lunatic.
Larry gets a satellite dish, but Tina is hellbent on taking it down. So Larry decides to run for president of the residents against Tina. Amanda likes the way Tina has whipped Brad so she too gets herself a *nice* man, Chucky.
Henry's parents are coming for a visit and he fears they'll be disappointed in him. Larry and Amanda have prejudices against them. Tina gets a job but she doesn't like Brad's excitement over it. Everyone may have to rethink their opinions.
Heather offers to do Tina a bridal shower. Brad suggests a Guys' Night to Henry & Larry. Tina authorizes it. In a bar Larry challenges Brad to put on his ladykiller alter ego. Who then hits on someone's girlfriend. Disaster in the making.
Larry doesn't like Amanda's new boyfriend Ross so there will be tension at Larry's indoor party between him and Amanda since Ross has other plans. Tina wants to dress Brad in a tux and have a romantic photo of them together outdoors.
Everyone's family Christmas plans get canceled so they gather at Larry & Henry's. But the shops are closed and the only Christmas Dinner is a ham outside the door of their neighbor. To take or not to take and play truth or dare instead?
Brad has forgotten the wedding preparations. He gives Tina an experimental pill for the migraine, with unexpected results. Larry's T-shirt business is on the verge of success. Amanda's boss is sexually harassing her. But does she need it?
Larry's holding his annual Halloween party, but Brad and Tina invite everyone to their party - and they accept. Heather and Henry are OK now, but Amanda has a hard time accepting Heather into the "gang".