Penny buys her first home, an "amah-zing" condo complete with a wine fridge and Italian marble. But will the new digs really signal "the year of Penny" and turn her life around? And, on the year anniversary of their almost-marriage, Jane encourages Alex and Dave to finally be honest with each other -- not the best of ideas.
Alex's cute line of slogan t-shirts for babies ("Put Me to Bed") become inappropriately popular with teen girls, who make her store their newest hangout. They're also in awe of Alex and Penny. Meanwhile, Jane channels her inner mom as she goes in search of her "egg daughter," the now 11-year-old girl she thinks is the result of the egg she donated in college.
Penny's perpetually optimistic mom, Dana, is in town for a singing gig at a boat show. Her enthusiasm inspires the gang, but when Penny finds out she's hiding some less-than-happy news, she decides it's time to give mom a reality check.
Jane convinces the gang to make vision boards so they can visualize their way to their dreams, only the universe isn't exactly listening; Brad has a difficult time relating to humorless boss Mr. Forristal until the guy, a car buff, flips for Max's limo; and Dave is reluctant to introduce his new girlfriend to everyone.
Jane and Brad spend a scary Halloween house sitting for friends in the suburbs, while the rest of the gang heads to a warehouse party, where their respective costumes don't quite have the effect they anticipated, especially for Alex and Dave.
When Brad hears that Jane's old sorority sister is coming for a visit, he lies and says he has a work retreat out of town, but he's actually on "staycation" in a fancy hotel in the city; Alex meets a new guy, Liam, but his dates are over-the-top; and Max and Dave make a commercial to promote the "Steak Me Home Tonight" food truck.
Angie, Max's high school girlfriend whom he dated before he figured out he was gay, moves back to town, and her arrival affects everyone: Penny is jealous of her (and then goes overboard befriending her); Alex develops her odd crush on Max; but the strangest reaction of all is from Max, who declares a "code war" when Dave and Angie date. Meanwhile, when Jane finds out Brad has a "work wife," she decides to get herself a "work husband" and sets her sights on the slightly unhinged head of Human Resources.
Jane needs a dress to wear to her charity event, but she's a little leery when Alex offers to design one for her; Penny helps a panicked Max babysit his niece and nephew; and Dave and Brad's new friendship with their oddball mailman, Drew, isn't quite what they had hoped for.
Max, desperate for cash, agrees to dress up as Santa for Penny's charity event; Jane accidentally gives housekeeper Gita the envelope stuffed with money for their big Xmas getaway to Turks & Caicos, instead of the $200 Christmas tip she had planned -- and she schemes to get the cash back.
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.