The family gathers to try and celebrate their parents' anniversary without spoiling it - like every other year. However, after everyone learns what Tom's new novel is about, the celebration may just be the worst one yet.

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.

After upsetting Marina, Tom tries to help out more around the house. While Sarah tries to find temporary employment, she and Denise worry their son will be corrupted after Kelvin decides he wants to learn all about Uncle Connor's business.

When Tom and Sarah discover that their parents have been spending time at Connor's house and not theirs, jealousy rears its ugly head. But when it looks like there might be more grandparent time for everyone, they learn to be careful what they wish for.

Connor invites all the cousins over for an epic sleepover to cheer up his daughter, Gretchen. Meanwhile, Tom is determined to prove he can be a fun uncle too. 

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.  .

The show takes a look at the heartwarming yet super uncomfortable and sometimes frustrating relationship among three adult siblings: one in the 1%, one middle-class and one barely holding on.