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 was looking forward to a first visit from father 'Big Dave' since his parents' divorce, less to him bringing a girl friend. Penny is elated to find it's her even weirder, hippie ma Dana Hartz, but her influence overturns all Dave's memories, so father)son quality time turns into a nightmare when dragged from a sports hero visit to a lame new age convention. Alex bought online a White Sypremacists's parrot and convinces Max and Brad that the Chinese restaurant across the street runs dodgy business, so the investigate undercover dangerously clumsily, only to ...
Dave is not amused when self-appointed fashion policeman Max mounts an 'in-t-vention' and ruthless indoor follow-up patrol against his mate's apparent addiction to V-necks, yet ends up confiding the youthful trauma root cause. Penny trues Jane's advice to change her dates instead of bending all over to accommodate and imitate them, but only molds her guinea-pig to his ex-bride's dreams. Brad wants to disprove that Jane shaped him by reverting to his sloppy student persona, but is tempted back by homely comforts.
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.
Max is sadly retreated in his unapproachable 'bear mode', using Dave's place as a cave where even the mates aren't allowed. So the rents of the gang eagerly awaits his annual wake-up call: Brad and Jane's theatrical spring fight, make-up and expensive celebratory dinner. However it's late, and every effort to trigger it seems to fail as if affected by a butterfly effect, but in fact they agreed only to fake fights and make up quietly.
Grant keeps proving himself the perfect boyfriend for Max, whose search for a flaw to escape ends when he's ready to commit, over the surprise subject of child wishes. Dave is on a winning streak after turning his food truck into a cocktails hype, attracting friendly attention from Hollywood B-star Colin Hanks, so he fears the new fame may be estranging his friends from him, but the gang actually gradually discovers they all get unsavory sex dreams starring Dave, except Alex, who ends up actually in his bed, after failing the diet from yogi therapist Avi she failed at...
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.