Holly accidently convinces Stuart to quit his dental practice and buy a restaurant. Haskell, sick of paying alimony, tries to persuade his ex wife Margo to marry her fiancé.
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.
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.
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.
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 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.
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.
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.
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’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 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.
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.