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 represents Nicki in her divorce, but her history gets in the way.
Holly joins a grief support group to meet a man. Stuart and Haskell help prepare Phil for a talk show appearance after he develops a lisp.
Phil is convinced that the woman Haskell is dating is really a man; Stuart feels guilty.
Haskell’s estranged brother shows up and asks for one small favor: his kidney. Holly mentors a teenager who turns out to like Eden’s job more than hers.
Holly throws a birthday party for Stuart and Nicki, but her real motive is to impress a guy.
Haskell is quarantined with Phil and Stuart; Holly secretly rewrites Eden's college paper.
The gang attends a silent auction for charity; Haskell wins a police ride-along; Phil gets a dinner.
Holly sneaks into a sorority that Eden is pledging, hoping to learn why she was rejected years ago.
Holly introduces everyone to her new boyfriend, Congressman Charles Hayward.
When a scandalous picture of Holly shows up in the newspaper, her engagement is put in jeopardy.
Holly's wedding day arrives; business partners Haskell and Nicki strike it rich.
After receiving a voice-activated operating system as a gift, Holly becomes overly attached to it; Haskell comes into money and controls Phil and Stuart with it.
Tired of dating drama, Holly decides to only pursue men she is not interested in; Haskell takes all of his money out of the bank.
Phil leads a rebellion after Stuart recruits him for his a cappella group. Also, Haskell angers Holly when he leaves her out of his will.
Stuart's sister returns from her European vacation with a female lover, which inspires Holly to start dating women.
Haskell moves out after a fight with Phil and Stuart, but Holly forces them to bring him back.
Phil begins dating an actress following a stint on a movie set while Holly has to fire someone for the first time.
Phil makes a mistake on his first date, so Holly must infiltrate the red carpet to help him; Stuart and Haskell compete for Twitter followers.
Holly and Nikki compete for a guy on a girls' night out; Phil realizes that dating a movie star is more difficult.
Holly convinces Stewart to quit his practice and buy a restaurant; Haskell tries to persuade Margo to marry her fiancé.
Stuart and Holly convince Margo to hold her wedding at the restaurant; Haskell tries to stop the wedding of Margo