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.
It is the day of Holly's wedding and business partners Haskell and Nicki manage to strike it rich.