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.

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.

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 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.

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.

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.

After Alex leaves her fiance, Dave, at the altar, they struggle to maintain relationships with their mutual friends.

Dave's fling begins turning into a relationship he doesn't want; Jane tries to help Alex find a roommate.

Jane thinks she and Brad should befriend a sophisticated couple; Max and Dave notice that things are disappearing from their apartment; Alex starts dating an artist.

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.

With the wedding coming up, Penny decides to reach out to her estranged dad Roy. The reunion is sufficiently awkward but Alex encourages Penny to be optimistic, while Jane is more skeptical. Meanwhile, Dave enlists Brad and Max's help in sabotaging "The Brazilian" food truck, a.k.a. Dave's #1 nemesis, but Max accidentally falls for the enemy's son and has to choose between his best friend or boyfriend.

When Brad's dad receives good news on some medical tests, his new view on life is difficult for Brad to accept; Penny meets an attractive Italian, but she can only speak to him when she's drunk.

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

A big chain coffee store becomes Alex's competition; Dave runs into his high school teacher.

Alex's string of "girls' nights out" doesn't sit well with Penny; Max pushes Dave to get even.

A concert outing goes awry.

Alex and Jane's sibling rivalry heats up; Dave dates an attractive woman (Bre Blair) with an unusual quirk; Penny gets an assistant

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.

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 discovers that Jane's old sorority sister is coming for a visit, so he lies and says he has a work retreat out of town, when he's actually on "staycation" in a fancy hotel in the city. Penny becomes jealous when Alex dates her former boyfriend Liam, and Max and Dave make a commercial to promote the "Steak Me Home Tonight" food truck.

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.

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.

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.

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.

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.