Holly attempts to become a matchmaker after Haskell declares his love for Nicki. Stuart arranges for Phil to meet his crush.
Holly represents Nicki as she seeks a divorce, but her history manages to get in the way. Phil attempts to prove he is not getting old.
Holly looks for a boyfriend at a grief support group. Stuart and Haskell help Phil get ready for a talk show appearance after he suddenly develops a lisp.
Haskell begins dating a beautiful woman, that Phil is convinced is actually a man. Phil manages to convince Holly to dress up in drag to try and see if Haskell's date shows any interest. Stuart feels guilty for sleeping with a woman who believes he is a war hero.
Holly mentors a teen, who likes Eden's job more then Eden does. Haskell's estranged brother turns up.
Holly decides to throw a birthday party for Stuart and Nicky in hopes of impressing a new man in town.
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.
The gang attends a charity silent auction. Haskell wins a police ride-along. Phil wins dinner with his favorite sitcom TV Mom. Stuart and Holly are forced to share a cooking lesson with a celebrity chef.
Holly's new boyfriend, Congressman Charles Hayward, is introduced to everybody.
After a scandalous picture of Holly ends up in the newspaper, her engagement is left on the line.