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.
Determined to try and live in the moment, Sophie and the gang head to an exclusive new club for a wild night out. Valentina has doubts about her relationship with Charlie. Sid pushes Jesse to be open to love. Ellen tries her luck with women at the club.
While helping Jesse take photos for his new Tinder profile, Sophie feels sparks with someone unexpected. Valentina helps Sid with his long distance relationship. Ellen and Charlie go apartment hunting.
Sophie discovers that hosting her thirtieth birthday party is almost as stressful as turning thirty. Jesse and Ellen struggle to relate as siblings. Val and Charlie spice things up. Sid shows off a new piece of bling.
An unexpected visit from Sophie's mom heightens Val's concern for her friend. Charlie helps Jesse and Sid face past traumas. A culinary quest leads Ellen to someone new.
A parental wrench is thrown into Sophie’s plan for the day. Jesse deals with the aftermath of a truth bomb. Charlie tries to get the gang excited about soccer.
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 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.
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 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.
