The Hayworth family is invited to the wedding of longtime family friend Spags. When Connor enlists Tom’s help to write and re-write a wedding toast, things take an unexpected turn between the brothers. Sarah realizes Denise is upset they never had a real wedding, while Marina meticulously plans her drinking schedule for a night out without the kids.
Connor invites the siblings to a party he’s throwing for his ex-wife, Emily. While he feels the need to prove that he is cool with their divorce, he is not the only one in the competitive spirit. Tom and Marina try to prove to each other that they still have game, while Sarah finds the perfect solution to the fact that she’s a bad gift-giver.
Connor invites the Hayworth clan to a San Francisco 49ers game as he tries to close his latest business deal. Desperately trying to prove that he knows the game, Tom gets a once-in-a-lifetime chance to showcase his football skills in front of the entire crowd of 49ers Faithful at Levi’s Stadium. Meanwhile, Denise tries to get Sarah to come to terms with Shamiah’s new interest in cheerleading.
As Tom struggles to finish his book before his 40th birthday, his dad Marshall hijacks his writing seminar. Denise convinces Marina that she needs to do something special for Tom’s 40th and talks her into doing boudoir photos. Elsewhere, Sarah and Denise go overboard to impress a potential sperm donor.
The success of Tom’s book sparks a change in the financial tides; and, with the extra cash in hand, Marina encourages him to spend some money on himself. Meanwhile, Denise’s parents shake things up during their visit to town. With their reveal of some surprising news, an unexpected Hayworth comes to her rescue.