An altar-bound couple break up on their wedding day, forcing their friends to choose which side to take after the split.
Cast: Eliza Coupe, Elisha Cuthbert, Zachary Knighton, Adam Pally, Damon Wayans Jr., Casey Wilson
The third Kerkovich sister, Brooke, is the alpha sister of the group, and Jane has the daunting task of planning a wedding for her more perfect and exquisite older sibling. Meanwhile, Brad is having a tough time himself dealing with Brooke's equally more perfect African American fiance, Elliot (guest star James Lesure), and Alex and Dave have a big secret they're hiding.
Penny's mom, Dana, and Dave's dad, Big Dave, are in town visiting, and these two lovebirds are not only going strong, they've decided to adopt a baby together, prompting Penny and Dave to react the only way they know how - irrationally. Meanwhile, Brad and Jane want some time just to themselves and decide to try to join an exclusive tennis club, but unfortunately Max is on the scent and they can't shake him...or Alex.
Chase, the ex-roommate whose life Max ruined, says he'd like to take revenge and do the same thing to Max, but Max's life is so pathetic it's "un-sabotagable." Max vows to prove him wrong and asks Jane to help him get his act together. Meanwhile, Alex asks the rest of the gang for help when Dave challenges her to finally use her stockpile of Groupons.
The gang is shocked when Penny rebounds from her breakup with Pete by having a torrid affair with the last man on earth they'd pick for her -- the Car Czar. To make matters worse, she's temporarily living with Brad and Jane, who end up acting like disapproving parents. Meanwhile the friends pressure Max to get a job so he'll stop sponging off them. He decides to enter the "Mr. Gay Gay Chicago" pageant, with Alex and Dave as his coaches.
Penny insists that she's fine after her breakup with Pete, but the gang begin to wonder when she writes a play entitled "Black Plague: A Love Story" and asks Derrick and his theater group to stage it. They brace for "drama" in more ways than one. Meanwhile a marketing group asks Alex and Max to be tastemakers, but is it a scam?
Brad and Jane host a couples game night with Penny, Pete, Max and Scotty and the competitiveness gets a little out of hand, prompting Penny to make an unexpected move. Meanwhile Dave has a big decision to make on the career front, and Alex tries to help but they end up at a psychic instead.
With the wedding coming up, Penny decides to reach out to her estranged dad Roy. The reunion is sufficiently awkward but Alex encourages Penny to be optimistic, while Jane is more skeptical. Meanwhile, Dave enlists Brad and Max's help in sabotaging "The Brazilian" food truck, a.k.a. Dave's #1 nemesis, but Max accidentally falls for the enemy's son and has to choose between his best friend or boyfriend.
When Max tries out Jane and Alex's long-time hairdresser, Krisjahn, he gets some good salon gossip on the girls, but his loose lips may cause World War III between the Kerkovitch sisters. Meanwhile, the Steak Me Home truck is stolen and Dave and Penny try to figure out whodunit -- but are perplexed by what they find when they finally locate the thief.
Max meets a cute girl who is a season tickets holder for the Bulls, leaving him no choice but to pretend to be straight, of course! Meanwhile, Alex is tired of everyone dismissing her as the dimwitted blonde, so she becomes well read to prove them wrong. However her newfound knowledge completely throws the whole group dynamic off and no one likes it.
Brad uses his skills, plus help from the gang, to prop up Chuckles and Huggs after the gym's loopy owner, Terry (guest star David Alan Grier), tells him it may be closing. Meanwhile, Penny and Max try to break the habit of texting the men in their lives (Pete/the new guy Max is dating). They turn to NocheTussin, a black market cough medicine, to help them sleep when they'd normally be texting.
When Penny learns that Pete wants to elope, Jane takes them to a wedding expo in hope of changing his mind; Dave and Alex deal with their unresolved issues.
Max vows revenge when the gang tricks him into thinking he won the lottery; Max's plotting interferes with a proposal from Pete; Brad gets a new job.
Brad and Jane catch up with their exes, while Dave and Alex help Max find his awesome new roommate. Meanwhile, Penny tries to hang with Pete's friends, but tries to convince Pete that her friends are more fun.
When Alex gets everyone to play on her store-sponsored kickball team, Jane defects to a better team and Dave freezes whenever it's his turn.
Penny enacts an all-out publicity bonanza when a pop star shops at Alex's store. Brad and Dave try to make some home repairs, and Max needs to get out on the town.
Brad and Penny create one disaster after another when they accidentally break a childhood memento of Alex's. Jane and Dave go overboard to find someone for Max.
When the gang finds out Jane lied about being born on Christmas Day and never got her own celebration, they throw a Christmas-free birthday party for her.
Penny's new relationship forces Max to look for a new BFF. Alex hasn't told her parents she's back with Dave, and Jane wants to think of a funny toast to make her grumpy father laugh.
Jane asks Brad for help when she hits a glass ceiling at the auto dealership. Penny has to wear a helmet following her concussion, and Dave and Max have fist-bump problems.
When the gang celebrates Thanksgiving at Alex and Dave's new apartment, Max brings along a tape of Brad and him on "The Real World," and everyone recalls how they met ten years ago.
Max becomes a popular emcee on the Bar Mitzvah circuit, and he asks Brad to help him out. Alex and Dave vow not to take their renewed relationship for granted.
Dave and Alex go apartment hunting, but their inability to commit to a place puts their real estate agent to the ultimate test. Meanwhile, Jane takes negotiations to crazy levels when she helps Penny shops for a car; and professional freeloader Max shows a cash-strapped Brad how to spend the perfect Saturday in Chicago with no money at all.