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.

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.  

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 the Hayworth clan to a San Francisco 49ers game as he tries to close his latest business deal. Tom gets a chance to showcase his football skills, Denise tries to get Sarah to come to terms with Shamiah's new interest in cheerleading.

Tom attempts to keep Connor grounded after he announces his plans to go to space then falls into a rough patch himself after learning some bad news. Meanwhile, Marina gets stuck while trying to transform their attic into a writing space for Tom.

Tom finds out that Connor is his new boss, which threatens to ruin Marina's perfectly planned trip to the Happiest Place on Earth - Disneyland Resort in California.