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'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.