Jane has the off-putting job of planning older sister Brooke's wedding. Perfect Brooke is the alpha sister of the group and Brad is having a tough time dealing with her equally more perfect African American fiance. Dave and Alex are hiding a big secret.
Penny and Dave react absurdly when they find out that lovebirds Dana and Big Dave want to adopt a baby together. Wanting time for just themselves, Brad and Jane join an exclusive tennis club.
Chase wants to destroy Max for ruining his life but declares Max's life as " un-sabotagable ". To prove him wrong, Max goes to Jane to help him get his act together. Dave urges Alex to use up all her Groupons, so she asks the gang for help.
Penny moves in temporarily with Brad and Jane and starts a rebound romance with the Car Czar. When the gang pressures Max to get a job and stop sponging off them, he enters the "Mr. Gay Guy Chicago" show.
As Penny deals with her breakup with Pete, she writes a play titled " Black Plague: A Love Story" and asks Derrick's theater group to participate. Alex and Max are asked to be tastemakers.
Jane and Brad decide to have a couples game night but things get cutthroat which in turn triggers an unexpected move by Penny. When Alex tries to help Dave with a big decision they end up at a psychic.
Penny seeks out her estranged dad Roy to be at her wedding. With help from Brad and Max, Dave sets out to sabotage his food truck nemesis but Max find himself in a dilemma when he falls for the enemy's son.
Max gets some gossip on Jane and Alex after he uses their long-time hairdresser, but his big mouth may create a war between the sisters. Dave and Penny set out to find who stole the Steak Me Home truck.
Max pretends to be straight when he meets a cute girl with season tickets for the Bulls. Tired of being the dumb blonde, Alex decides to become well read which in turn throws off the group's dynamics.
Brad applies his business skills to keep Chuckles and Huggs open. While Penny and Max try to break their texting habits, they turn to Noche Tussin so they'll sleep instead of texting.
Would-be wedding coordinator Jane tries to talk Pete and Penny out of eloping by taking the gang to a wedding expo. At the expo, Max and Brad end up in the gay wedding part while Alex and Dave are forced to deal with their own wedding issues.
Max is out for revenge when the big lotto jackpot he thought he won turns out to a prank. Pete proposes to Penny. Jane is not amused by Brad's new job.
Brad meets Jane's ex, Ryan, and discovers she's a woman. Max's new roommate, Chase, outfits the apartment with expensive furniture and gadgets and then suddenly disappears which starts the gang snooping to find out who Chase really is.
Alex is sponsoring a team for the city Kickball Tournament and convinces everyone but Jane to be on her team. They might have a shot at winning except that Dave freezes when it's his turn.
Alex and Penny see a way to use the press when a pop star buys a dress from Alex's shop. While Max has an identity crisis, Dave and Brad attempt to fix some things around the house.
While Alex is away at her Rom-Com Com, Brad and Penny accidentally break her favorite childhood memento. While attempting to glue it back together, Alex's racist parrot dies from the glue fumes. Jane and Dave go overboard trying to find a match for Max.
Jane's big secret is out - she was born on December 25. She's been lying about her birthday because she didn't want it to be overshadowed by the holiday. Everyone decides to quit Christmas and throw Jane a Christmas-free birthday celebration.
Jane labors to come up with a joke that will make her dad laugh when she toasts her parents at their party for the 20th anniversary of the family mattress business. Dave finds out that Alex hasn't told her parents they're back together. Since Penny is occupied with a new boyfriend, Max goes looking for a new BFF.moreless
Penny's got a new guy but the helmet she has to wear because of her concussion may put an end to the romance. Jane tenaciously pursues being part of the "boy's club" at the car dealership. Painful childhood memories flare after Max and Dave fist bump.
The gang spends Thanksgiving dinner at Alex and Dave's new place where Dave is determined to share a real Navajo Thanksgiving. When Max pulls up a copy of the lost season of "The Real World", everyone starts reminiscing about how they all met ten years ago.
Max has been working as a professional "hype guy" at Bar Mitzvahs but, when he teams up with Brad to form a "hype guy" duo, jealousy and tension take hold. Jane pushes Alex and Dave not to take each other for granted this time around.
Dave and Alex can't seem to agree on an apartment. When Penny needs a car, Jane negotiates for her. Max introduces Brad to the techniques for having a night out free.
Alex and Dave are dating again. Penny's accident leaves her in a full body cast, but when Max falls for her physical therapist, he tries to slow down her recovery. Brad hides a secret about his unemployed status from Jane.