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.
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.
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.
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.
Brad uses his skills, plus help from the gang, to prop up Chuckles and Huggs after the gym's loopy owner, Terry tells him it may be closing. Meanwhile, Penny and Max try to break the habit of texting the men in their lives.
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.
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.
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.
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.
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.
Max has become a hit on the Bar Mitzvah circuit as an energetic emcee and allows Brad to partner up with him, but not everything turns out kosher. Meanwhile Dave and Alex make an effort not to take their relationship for granted.
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.
A fresh and funny take on modern friendship and what one urban family will do to stay friends after the perfect couple who brought them all together break up on their wedding day. The failed wedding forces them all to question their life choices. Then there are Alex and Dave themselves, who strike a truce and must learn to live with the changes their breakup has brought.