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.

The gang discovers that Jane has been lying about her birthday, and that she was actually born on Christmas but never liked her natal day being trumped by the holiday. With that in mind, they throw her a celebration that is Christmas-free and all about Jane.

When Ryan, Jane's ex, comes to town for a visit, Brad is surprised to learn that Ryan is a woman. Meanwhile Max gets a super cool new roommate, Chase, who immediately upgrades the apartment with expensive furniture and gadgets. The gang is in awe, but when Chase suddenly disappears, they start snooping into his private life.

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.

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.

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.

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.