Dave has an odd reaction when his shrink starts dating Penny. Meanwhile, Jane and Max fight over ownership of a sweater and end up in another one of their strange competitions; whoever is "less vain" gets to keep the sweater, and the challenge is to see who can wear a horribly unflattering outfit the longest. And Jane urges Brad and Alex to try and "bond," but it's awkward -- until they discover their mutual love of romantic comedies.
Dave's father, "Big" Dave, comes to town to introduce his new girlfriend, who shockingly happens to be Penny's mother, Dana. Penny couldn't be more thrilled that her thrice divorced mother has a new man in her life, but Dave on the other hand reacts childishly to the news. Meanwhile Alex, who is feeling lonely at the shop, decides to adopt an adorable parrot that turns out to be not so charming, spewing nonstop racist and homophobic rhetoric. And Alex enlists Brad and Max's help, as she is convinced the Chinese restaurant next door is a front for a brothel.
Jane convinces Penny to stop changing herself for every guy she dates, and instead to change the guy to suit her needs. Penny's first experiment is Jeff, a slacker who is 30 going on 20. Meanwhile, when Brad overhears Jane bragging to Penny about how she completely made him over after they met, he rebels, and starts walking, talking and dressing like his college-era self. And Alex and Max stage an "in-T-vention" to stop Dave from his obsession with v-necked T-shirts.
For Valentine's Day, Brad tries to surprise Jane, who doesn't respond well to surprises. Penny begins the process of breaking up with her boyfriend, 'respecting the break-up window'. Max solicits his friends for Valentine's Day limo packages. Dave misinterprets his girlfriend's intentions. Alex tries to find love at a party. Brad gets his first cavity.
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.
Some people wait for the groundhog to signal the end of winter. Instead, 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.
Once Dave gets a liquor license for the "Steak Me Home Tonight" truck, it suddenly becomes the next big trendy place in Chicago. He thinks his friends are avoiding him because they're jealous of his newfound fame, but there's another reason: His signature drink is giving almost everyone sex dreams - about Dave -- Everyone except Alex, who is on an alcohol-free fast.
A panicked Alex enlists Jane's help in convincing Dave that something he's certain happened never did, but will they succeed? Meanwhile, Penny and Max are determined to finally beat an annoyingly perfect couple in the annual Rosalita's Run and Scavenger Hunt.
So many bad things have happened every time the friends celebrate Penny's birthday, they're wondering if her special day might be cursed. They set out to find a restaurant where they can celebrate, where one of them hasn't been banned or where someone won't run into an ex -- something that's almost impossible.
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. But when Penny tells Jane to "sleep on it" before she does anything rash, her advice results in an all-new, suddenly chill Jane.
In order to avoid having tea with an annoying childhood friend, Penny (Casey Wilson) makes up a series of detailed lies that quickly spin out of control. Meanwhile, Dave (Zachary Knighton) and Max (Adam Pally) struggle to convince their nosy landlord to fix their oven.
The gang find themselves at yet another wedding, this time the nuptials of Derrick and Eric . Will there be "DRAMA", to quote Derrick? Of course, as 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 down-scaled; 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 a cute guy via Skype.
Alex signs up the gang to participate in the Northside Kickball Classic tournament. However, self-appointed manager Max has difficulty bringing his players up to scratch - Dave has a history of freezing at crucial moments after an unfortunate incident during a previous game, Penny uses the tournament as an opportunity to meet good-looking guys and refuses to put on appropriate footwear, while Jane abandons her friends altogether and started playing for another team.