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.

Holly searches for a boyfriend at a grief support group; Stuart and Haskell help Phil prepare for a talk show apperance when he suddenly develops a lisp.