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.

Penny meets a terrific new guy, Pete, but her frantic attempt to hide the fact that she's wearing a prescription helmet because of her concussion really limits their potential romance. Jane tries to break into the "boys' club" at the car dealership and enlists Brad to be her "trophy wife". Max and Dave's fist bump issues bring back painful childhood memories.

Jane and Alex's parents throw a big celebration to commemorate the 20th anniversary of the family mattress business, and Jane agonizes over coming up with an amusing toast to spring on her humorless dad. Meanwhile, Alex tells Dave that her parents are unaware that they are once again bedfellows, and Max goes looking for a new BFF since Penny's tied up in her relationship with Pete.

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.

When a hot young pop star stops in and buys a dress at Alex's store, Penny helps Alex turns it into a press opportunity. Meanwhile, Max is having an identity crisis, so Jane and Derrick take him on a tour of Chicago's themed gay bars to help him find his niche, and Brad and Dave try to be "men" and fix things around the house.

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.

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".

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.

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.

Brad plays matchmaker to a co-worker; Penny regrets inviting Jane to her martial-arts class; Dave helps Alex with odd jobs, leading his friends to think he wants to get back together with her.

Dave has a surprising reaction when his shrink starts dating Penny. Max and Jane's fight over a sweater leads to a strange competition, and Alex and Brad bond when they discover a shared interest.

When Brad's dad receives good news on some medical tests, his new view on life is difficult for Brad to accept; Penny meets an attractive Italian, but she can only speak to him when she's drunk.