Great friends. Meh decisions.
In the near future, Sophie tells her son the story of how she met his father: a story that catapults us back to the year 2021 where Sophie and her close-knit group of friends are in the midst of figuring out who they are, what they want out of life, and how to fall in love in the age of dating apps and limitless options.
After Sophie's gallery show and Ian's arrival, Sid and Hannah host an impromptu wedding reception at Pemberton's. Jesse grapples with his decisions and confides in Ellen about Meredith.
As she waits for the gallery to call, Sophie lands a gig she lied to get and enlists Val to help. Jesse forces Sid and Meredith to work out their differences.
After selling her portrait, Sophie recruits Jesse to help her impress the buyers. Val and Ellen go on a double date. Charlie forces a reluctant Sid and Hannah into a double date in reaction to Val.
Sophie and Val question where they are in their careers and reach out to an old friend. Jesse and Meredith make a tour announcement video.
Sophie and Val have conflicting feelings about brunch with Val's parents. The gang attends Jesse's Long Island show.
Sophie encounters an obstacle with a new beau. Ellen uses her new job insurance to see a therapist. Jesse gives Valentina a hand at work while Sid and Charlie try to sell terrible wine.
The gang recounts their worst Valentine's Day experiences in order to cheer up Ellen.
Jesse and Sid introduce the gang to an old college ritual. They all spend the next 48 hours attempting to complete various tasks in order to achieve a group "rewardishment."
Val brings Sophie to a work event so they can party all night with the rich and famous. Jesse wants to introduce the friends to a new girl he's seeing, forcing them to spring into action and invoke the "Welcome Protocol".
Sophie dates an older man, which encourages Jesse, Sid, and Charlie to take better care of themselves. Sophie and Val battle over who gets the apartment for date night.
Sophie goes to Robert's country house for the weekend. The gang celebrates Lost & Found Box Day at Pemberton's.
Sophie recruits the gang to help track down her father.
Sophie and her dad run a business out of Pemberton's. Charlie and Jesse meet women they like. Val and Ellen treat themselves to a fancy open house.
Sophie pulls in the big guns to help her get Val out of her engagement. Sid and Hannah argue about where they'll live. Jesse helps Charlie and Ellen through a roommate faux pas.
Sophie and Ellen get assigned to a work project together. Sid surprises Hannah in LA. Charlie and Val try to make the most of their time with Jesse after he gets a bad psychic reading.
Ellen suspects something is up with Rachel. She and Sid do a stakeout. Sophie tracks an upset Jesse down after he wasn't invited to a coworker's birthday party.
The gang go a day without their cell phones, forced to face the world without help from the internet.
Sophie tries to Parent Trap her parents. Sid and Ellen try their own master plan to nudge Jesse and Charlie into being roommates with each other.
Jesse tricks the gang into helping him pack his stuff in the apartment.
Everyone heads to Pemberton's to weather out the hurricane.
