Katie is feeling tired, old, and unattractive - all compounded by the approach of her 40th birthday. But then Doris's husband Richard informs Angela that he intends to divorce her (so that Angela, a lawyer, now cannot represent Doris, a trick he learned from Big Little Lies). Katie and Angela try to break the news gently to Doris, who decides that if she's going to be single again, she intends to celebrate. So the Second Breakfast Club goes for a night on the town and Greg allows Katie to pretend to be single to prove she's still attractive. Greg has an ulterior motive, though - he intends to re-create a beloved family photo he gave to Katie for her 30th birthday, and figures they may not have another chance to take the picture. But Taylor and Oliver both have plans to see a movie with Trip and Cooper, and neither wants to stay, forcing Greg to find creative ways to ground them to make sure they participate.
Tropes:
- A Day in the Limelight: Doris gets her own storyline in this episode, regarding her divorce from Richard. Angela also appears throughout, though mostly in support of Doris.
- Disproportionate Retribution: As part of his scheme, Greg grounds Taylor for making a perfectly innocuous joke. This spooks Oliver, who immediately becomes wise to Greg's plan, into acting like a perfect angel until it's time to leave for the movie... only for Greg to plant "marijuana" (actually Italian seasoning) on Oliver's pocketless jacket. Oliver immediately points this out and refuses to go along with it until Cooper convinces him that he really should.
- Milestone Birthday Angst: Katie's self-esteem takes a hit around the time of her 40th birthday.
- Shout-Out: To Big Little Lies, where a character played by Meryl Streep pulls the same trick that Richard does here. Called-out In-Universe.
- Significant Reference Date: Taylor and Oliver want to go out to see "the new Terminator movie". Terminator: Dark Fate was released on November 1, 2019, the same day the episode first aired.
