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.
s04e01 - The Devil Wears Hanes
s04e02 - The Wedding Unplanner
s04e03 - Love and Death
s04e04 - An Officer and a Dental Man
s04e05 - Oh Brother Here Art Thou
s04e06 - Dawn of the Dad
s04e07 - Catch It 'Cause You Can
s04e08 - Requiem for a Dream
s04e09 - Get Her to the Greek
s04e10 - Holly Franklin Goes to Washington
s04e11 - A Bride Too Far
s04e12 - The Wedding
s04e13 - Him
s04e14 - Finding Mr. Wrong
s04e15 - Good Will Hinting
s04e16 - The Forty Year Old Her-Gin
s04e17 - Haskell Doesn't Live Here Anymore
s04e18 - Knotting Phil
s04e19 - 10 Things They Hate About You
s04e20 - Gone Girls
s04e21 - What Dreams May Come
s04e22 - Along Came Holly
Three divorced men share an apartment across the hall from their female divorce attorney, who is also their landlord.
The "never been married" Holly introduces her newest single client Stuart to his new roommates - ladies' man Phil and the sardonic homebody, Haskell. Things get off to a shaky start for Phil and Haskell when they begin to have reservations about living with clingy Stuart, but Holly is right across the hall to help them steer clear of any catastrophes.
After all, it helps her to avoid her own relationship and commitment issues! To top it all off, Holly's hard-partying assistant Eden, doesn't let her professionalism get in the way of prying into her boss's personal life. Through the episodes, the guys begin to realize that the issues they have with each other are the same ones that they had with their ex-wives.