Single and miserable at 35, Olivia plunges into the world of online dating, with the help of Mary, her recently widowed mom, and Jayne, her younger, married sister.

Olivia dates a younger guy, causing Jayne to evaluate just how much spontaneity is in her own marriage.

Olivia meets a great guy, but he may have a major deal breaker. Meanwhile, Jayne decides to try one of Olivia's new sex tips on Jim.

Olivia dates one of Jim's geeky co-workers, Mary goes out with a celebrity, and Jayne has serious mother-in-law issues.

Olivia runs into her ex, hoping to rekindle the past, while Mary tries to land a job— her first ever.

Olivia sees a doctor about freezing her eggs, while Jayne secretly chats with one of Olivia's matches… as Olivia.

Olivia starts to date Charlie, Jayne's Tinder crush, so Jayne throws a dinner party to meet him.

Olivia's insecurities grow as she falls for Charlie, causing frustrations with her mom to boil over. And Jayne makes a decision that could affect her marriage forever.