As Julia and Sean's daughter Annie faces puberty, they must both face the harsh realization of maturity and deal with their own issues about getting older. When Gina tells Christian he can no longer be involved in Wilbur's life, Christian is forced to reach out to an old flame in order to build a case to gain sole custody of Wilbur.
Mrs. Grubman returns wanting to get her knees done. The doctors refuse and Christian resorts to his own threats against her causing her to break down emotionally and confess that she needs it to be strong for her daughter who has breast cancer. The doctors agree to do it.
Julia discovers that Annie is maturing. She talks about it with Suzanne and learns that Suzanne is now eating healthier and is more healthy.
James visits Christian and offers to help him get custody of Wilbur because he read Gina's diary and because he doesn't want to tell his wife and kids that they have to raise another one. He also tells him that Gina is calling character witnesses i.e. Kimber.
Christian has dinner with her and after refusing her advances, learns that she is snorting drugs and has ruined her nose. He offers to fix it for free if she will not testify against him.
The doctors operate on Grubman and she arrests soon after being anesthetize because she had been taking anti-depressants. They learn that she suffered great neurological damage.
Annie, after hearing what Matt had to say about maturing, uses her mom's tampon and becomes seriously ill. Sean figures out what it may be and Annie says she doesn't want to get older. Julia decides not to change their diet.
Christian and James are at a church getting Wilbur baptized. There Christian learns that James has decided to keep the baby, devastating Christian. In the end, we learn that Kimber has become a porn star.
- Famke Janssen (Ava) was credited as a "Special Guest Star", but she didn't appear in the episode
- It is revealed that Gina had 292 sexual partners in the last three years.
- "Satie's Blues" by Margaret Leng-Tan (Annie's 'Princess Menses' tea party/Kimber getting ready/meeting Christian for lunch)
- "Baby" by Koop ft Cecilia Stalin (Christian & Kimber at lunch)
- "Cosmopolitans" by Erin McKeown (Kimber at lunch with Christian/doing coke in bathroom)
- "Humble Girl" by Anjali (Kimber returns from the bathroom & her nose starts bleeding at the table with Christian)
- "Mother's Little Helper" by Rolling Stones (Mrs. Grubman's knee surgery/flat lines)
- "Moonlight Sonata" by Dakesh York (Kimber's nasal reconstructive surgery)
- Christian: (to Mrs. Grubman) Do you lie awake at night dreaming up ways to torture your body?
- Matt: Look, I'm sorry, guys, but I should not have to eat dog food just because you're worried about little princess' pubes [Annie] over there.
- Mrs. Grubman: (to Christian) I need you to do something for me, Dr. Troy. Fix my face.
- Christian: This time, I can´t. You´ve had neurological damage, and I can´t lift that, and I can´t repair it. I´m sorry.
- Mrs. Grubman: So that´s it. Then I lost the race.
- Christian: Who were you running against?
- Mrs. Grubman: Time.
- Julia: (to Annie) Why were you trying out one of Mommy´s tampons?
- Annie: Matt said I was going to leave a stain. I don´t want to get old and bleed.