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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 lets her own history with marriage get in the way. Phil tries to prove he’s not getting older by dating a much younger woman.
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 after sleeping with a woman who thinks that he is a war hero.
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 she's just met who's new in town. Nicki and Stuart's dad shows up and ruins everything.
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 sneaks into a sorority Eden is pledging to find out why she was rejected years ago. Haskell turns the guys' apartment into a pretend AirBnB to attract a woman.
Holly, over the moon, introduces the gang to her new boyfriend, Congressman Charles Hayward, but they soon begin to question his motives.
Holly’s engagement to Congressman Charles Hayward is put in jeopardy when a scandalous photo of her lands in the newspaper. Haskell has an idea for a great new app, but needs an investor.
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.
Stuart recruits Phil for his a cappella group and Phil leads a rebellion. Haskell leaves Holly out of his will and she seeks revenge.
Stuart’s sister Nicki comes back from her European vacation with a female lover. Holly, inspired by Nicki, decides to try dating women.
Phil and Stuart have a fight with Haskell and he moves out. Holly, desperate to keep them all together, sends Phil and Stuart to bring him home.
Phil’s stint on a movie set leads to romance with the female star. Holly struggles with having to fire someone for the first time.
Phil makes a big mistake on his first date with a movie star so Holly has to infiltrate the red carpet to bail him out. Stuart and Haskell compete over who can get the most Twitter followers.
Holly and Nicki plan a girls’ night out, but wind up competing for the same guy. Phil realizes dating a movie star is much more difficult than he imagined.
