In the wake of Haskell declaring his love for Nicki, Holly tries to play cupid. Stuart secretly arranges for Phil to get together with his high school crush.

Holly represents Nicki in her divorce, but lets her own history with marriage get in the way. Phil tries to prove he’s not getting older by dating a much younger woman.

Holly joins a grief support group to meet a man. Stuart and Haskell help prepare Phil for a talk show appearance after he develops a lisp.

Phil is convinced that the woman Haskell is dating is really a man. Stuart feels guilty after sleeping with a woman who thinks that he is a war hero.

Haskell’s estranged brother shows up and asks for one small favor: his kidney. Holly mentors a teenager who turns out to like Eden’s job more than hers.

Holly throws a birthday party for Stuart and Nicki, but her real motive is to impress a guy she's just met who's new in town. Nicki and Stuart's dad shows up and ruins everything.

Haskell plans to attend a big event honoring him for his past bowling glory, but is quarantined with Phil and Stuart. Holly secretly rewrites Eden's college paper and almost destroys her dream.