Holly dates an older man only to find he lives in an assisted living facility. Nicki comes to Phil with a proposition.

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 acts as Nicki's divorce attorney, but lets her own marriage history get in the way. Elsewhere, Phil dates a much younger woman to prove he's not getting too old.