When the gang pranks Max into thinking he won a big lotto jackpot, he vows revenge when they least suspect it. Meanwhile, Brad gets a new job as a CFO, but Jane is not amused when she learns the title is Chief Fun Officer and that Brad is working at a kids' gym.

Penny has a new boyfriend she wants to dump and Dave is afraid his new girlfriend is about to dump him. Alex goes looking for a party in the sketchy part of town, and Brad's hopes for a perfect night out for Jane are dashed when a dental appointment goes terribly wrong. Max picks up a couple with his limo only to find that one of the passengers is Grant, the boyfriend he broke up with a year ago.

Things spiral out of control after Penny tells a white lie to avoid an irritating childhood friend. Dave and Max's lonely and jealous landlord falls for Alex.

Dave gets a liquor license for his food truck, making it a new hot spot. The gang avoids Dave because his signature drink gives them sex dreams about him.

A panicked Alex enlists Jane's help in convincing Dave that something he's certain happened never did using "The Kerkovich Way," an ancient Serbian memory-wiping technique passed down through the Kerkovich clan. Meanwhile, Penny and Max are determined to finally beat an annoyingly perfect couple in the annual Rosalita's Run and Scavenger Hunt.

The gang find themselves at yet another wedding, this time the nuptials of Derrick and Eric. Brad struggles to tell Jane something important, Jane tries to find a way to help Eric hide the fact that the pricey reception must be downscaled, and Max tries to find the courage to perform with his old all-male Madonna cover band. Meanwhile, a dateless Penny is sad that she's at another wedding, alone, until she meets cute guy Chris via Skype.

Penny, Max, Dave and Alex head to a Halloween warehouse party, where their costumes don't have the effect they anticipated. Meanwhile, Jane and Brad spend their Halloween house sitting for some friends in the suburbs.

The friends wait for Brad and Jane's annual "Spring Smackdown," their yearly blowout of a domestic squabble, to let them know when Max will come out of hibernation and when winter will end.

After years of bad luck every time the gang celebrates Penny's birthday, the gang starts to believe the day is cursed.

When Max's high school girlfriend Angie, the girl he dated before he realized he was gay, returns to town, Penny (who was Max's girlfriend in college) starts to feel jealous. Meanwhile, Alex starts to develop an unusual crush on Max. When Dave starts dating Angie, Max becomes angry and declares a "code war". Jane finds out that Brad has a "work wife", so she sets out to obtain a "work husband".

The gang celebrates Thanksgiving by watching a previously unaired episode of "Real World" they appeared in back in college, and, long after the fact, learn some shocking new dirt about one another.

The gang discovers that Jane has been lying about her birthday, and that she was actually born on Christmas but never liked her natal day being trumped by the holiday. With that in mind, they throw her a celebration that is Christmas-free and all about Jane.

Max's friends encourage him to tell his parents he is gay; Penny meets her perfect man.

An old friend gets married, and the bride thinks Alex is a jinx; Penny and Derrick pretend to be engaged.

Alex and Dave to decide that they should be honest with each other. Penny buys a new condo and declares that it's "The Year of Penny", the year where everything will start going her way. Max tries to find out why Brad hasn't been hanging out with him lately.

Jane encourages Penny to find a man and then change him to suit her expectations. Alex stages an intervention to stop Dave from his obsession with V-neck shirts.

Brad uses his skills, plus help from the gang, to prop up Chuckles and Huggs after the gym's loopy owner, Terry tells him it may be closing. Meanwhile, Penny and Max try to break the habit of texting the men in their lives.

Brad and Jane host a couples game night with Penny, Pete, Max and Scotty and the competitiveness gets a little out of hand. 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.

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, and Alex and Dave have a big secret they're hiding.

Dave shocks everyone by quitting his job and plans to open a restaurant; Jane and Max face off in silly challenges; Penny is exhausted by trying to keep up with her new boyfriend's friends.

Alex's new T-shirts intended for children end up being a hit with with teenagers. Jane searches for the child she believes was conceived from an egg she donated years ago. Max starts working at Dave's food truck.

When the whole gang, with the exception of Dave, falls in love with Grant, Max wonders if he really is good enough to date the "perfect" guy. Meanwhile, Dave sets out to prove he's way cooler than Max's new boyfriend.

Dave finds himself bullied at the gym by Corey, and former bully Alex coaches him on how to fight back. Meanwhile, the residents at Brad and Jane's condo are fed up with Jane being too controlling as president of their home owners' association, and rise up to challenge her for the job.

Dave and Alex's inability to commit to a new apartment proves to be quite a challenge for their real-estate agent, while Jane pulls out all the stops when she takes Penny car shopping. Later, Max shows out-of-work Brad how easy it is to spend a cashless Saturday in Chicago.

Max meets a cute girl who is a season tickets holder for the Bulls, leaving him no choice but to pretend to be straight. Meanwhile, Alex is tired of everyone dismissing her as the dimwitted blonde, so she becomes well read to prove them wrong and in the process throws off the whole group dynamic.