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.

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.

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.

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.

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.

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.

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's father comes to town to introduce his new girlfriend, who turns out to be Penny's mother, Dana. Alex decides to adopt a pet parrot that turns out to be not so charming. Alex enlists Brad and Max's help, as she is convinced the Chinese restaurant next door is a front for a brothel.

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

Max agrees to dress up as Santa for Penny's charity event. Jane accidently 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. Dave cashes in all the homemade coupons Alex gave him as gifts from past Christmases.

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.

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".

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.

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.

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.

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.

The gang is shocked when Penny rebounds from her breakup with Pete by having a torrid affair with the last man on earth they'd pick for her -- the Car Czar. To make matters worse, she's temporarily living with Brad and Jane, who end up acting like disapproving parents. Meanwhile the friends pressure Max to get a job so he'll stop sponging off them.

Penny insists that she's fine after her breakup with Pete, but the gang begin to wonder when she writes a play entitled "Black Plague: A Love Story" and asks Derrick and his theater group to stage it. Meanwhile a marketing group asks Alex and Max to be taste makers.

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.

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.

After Brad and Penny accidentally break Alex's beloved childhood memento, they try to glue it back together which leads to an even worse situation. Meanwhile, Jane and Dave try a little too hard to find a match for Max.

Penny's mom Dana visits, however, Penny learns that her mom's inspiring upbeat attitude is hiding some bad news, which leads Penny to decide to give her mom a reality check. Max plays tour guide to some tourists in his new limo with the help of Brad and Jane.

When Max tries out Jane and Alex's long-time hairdresser, Krisjahn, he gets some good salon gossip on the girls, but his loose lips may cause World War III between the Kerkovitch sisters. Meanwhile, the Steak Me Home truck is stolen and Dave and Penny try to figure out whodunit.

Jane convinces Penny to make a vision board to visualize the path to her dreams, although everything doesn't go according to plan. Brad finds it hard to relate to his stern boss until the guy sees Max's limo. Dave is reluctant to let the gang to meet his new girlfriend.

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.

In order to get Pete to change his mind about eloping with Penny, wannabe matrimonial coordinator Jane spirits the whole gang to a wedding exposition. Once there, Max and Brad wind up at a gay-marriage part of the expo, while Alex and Dave contemplate their own commitment issues.

Dave and Alex start seeing each other again; Max tends to Penny after an accident lands her in a full body cast, but when he starts crushing on her physical therapist, he tries to impede her recovery; Brad tries to keep a secret from Jane.

Former couple Dave and Alex regret their couples tattoos; Jane feels Max is missing Mr. Right.

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.

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.

Penny's mom, Dana, and Dave's dad, Big Dave, are in town visiting, and these two lovebirds are not only going strong, they've decided to adopt a baby together, prompting Penny and Dave to react the only way they know how - irrationally. Meanwhile, Brad and Jane decide to try to join an exclusive tennis club, but unfortunately Max is on the scent and they can't shake him...or Alex.

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.

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.