Mary Anne inadvertently causes strife in the BSC when a coworker of her father's, Mrs. Delvecchio, specifically requests her as a sitter. Mary Anne tries to tell her father that she feels like a baby, but it goes awry — her father tells the BSC girls' parents, resulting in them ostracizing her. However, she befriends transfer student Dawn Schafer. At the Delvecchios', Mary Anne realizes that the child, Bailey, is a trans girl.
Dawn and her mother take Mary Anne to a cookout hosted by the Watsons' witchy neighbor, Esme, but she runs off when asked to speak. Dawn is understanding, to Mary Anne's relief.
Bailey gets a fever while Mary Anne is babysitting. She firmly asks the medical staff to stop misgendering Bailey. Her dad and the Delvecchios arrive. Richard agrees to start letting her start dressing differently. At the next BSC meeting the girls welcome Mary Anne back into the fold. The Spiers invite the Schafers over Thanksgiving, only for Dawn and Mary Anne to learn their parents are exes.
Tropes:
- Adapted Out: The character of Jenny Preziosso, a prim-and-proper but slightly tempermental little girl, is replaced by Bailey Dellvecchio, a transgender girl with the same "fancy" tendencies but a more even disposition.
- Adaptation Deviation: There are three basic changes from the book.
- In the book, Mary Anne calls her charge's parents, their neighbors, the girl's doctor, and Dawn (who comes over) before dialing 911. Here she's only shown calling the Dellvecchios before calling an ambulance, though it's later revealed that she did call her dad as well.
- In the book, Mary Anne is so stressed out by the days events that she forgets to mention to her father what happened; he only finds out when the girl's parents call to thank Mary Anne for her quick thinking and responsible behavior. Here, he witnesses her stand up to a pair of adults who are (unintentionally) misgendering a trans girl, and is impressed by how much she reminds him of her mother.
- In the book, Mary Anne and Dawn find out their parents knew (and dated!) each other in high school while looking through old yearbooks. Here, they have no idea until Dawn and her mom come to the Spiers' house for Thanksgiving.
- Apologizes a Lot: Mary Anne has a tendency to do this. She dislikes it, but is unable to stop until she decides to stick up for herself more.
- Apple of Discord: The other members of the BSC are not happy that Mrs. Dellvecchio wants only Mary Anne as a sitter, since it goes against the club rules. They're equally unhappy witih Mary Anne when she accepts the job.
- Black Comedy: When asked if she's new (because she's sitting alone in the cafeteria), Mary Anne darkly jokes to Dawn that all of her friends are dead, then reassures her that they're just absent (they were actually ignoring her at the time).Dawn: You're funny! Dark, but funny.
- Breaking the Fellowship: Mary Anne complains to her dad about all the things she doesn't like about herself, and he calls the other girls parents about their daughters "bullying", which ends up getting them all grounded and temporarily ostracizes Mary Anne from the group.
- Curly Hair Is Ugly: Played with; Mary Anne doesn't consider her hair ugly per se, but she thinks wearing it in twin braids makes her look like a child. When she asks her dad if she can style it differently, he readily agrees, saying the only reason he'd always done her hair in braids was that it was the only method of working with Black hair her mother taught him before she died.
- The Dreaded Pretend Tea-Party: Averted; Mary Anne is more than happy to take part in Bailey's "royal" tea party.
- Expository Hairstyle Change: Mary Anne stops braiding her hair at the end of the episode, and is wearing it more or less "natural", just pulled back.
- Foreshadowing: When Mary Anne complains about the way (she thinks) Kristy and the other members of the BSC see her, Richard makes it clear he doesn't agree with Elizabeth's parenting style, despite their being neighbors for years.
- From Bad to Worse: The tension between Mary Anne and the rest of the BSC isn't helped when, the day after their fight, Mrs. Dellvecchio calls and again requests Mary Anne to sit for Bailey.
- Layman's Terms: Dawn (whose being from California is used as a way to make her more knowledgeable about some things) helps Mary Anne understand Bailey being transgender by comparing it to someone who's always known they're right-handed being forced to use their left hand all the time.
- Needlework Is for Old People: To drive home that Mary Anne sees herself as "the world's youngest senior citizen", she's learning how to knit from Mimi, who's almost exactly seventy years older than her.
- New Transfer Student: Dawn, whose first day just so happens to be the day Mary Anne is eating lunch by herself due to the tension in the BSC.
- "Not So Different" Remark: Played with; Mary Anne knows she's very similar to her dad (quiet, reserved, shy), but doesn't think she has much in common with her mother. By the episode's end, Richard makes it clear that how she stood up for Bailey's rights is exactly like something Alma would have done, and tells her he's very proud of her.
- Old Flame: It turns out that Mary Anne's dad and Dawn's mom dated (very seriously, according to Aunt Esme) in high school, and when they meet again, it's clear they're still interested in each other.
- Pink Means Feminine: Mary Anne's room is painted pink, her bookbag is pink, and many of her clothes are pink. She's grown tired of this, feeling that it makes her seem like a baby.
- Poor Communication Kills: Mary Anne pours out her insecurities about herself to her father, but he thinks the other members of the BSC were saying those things and calls their parents to complain, leading to them all being grounded.
- Pregnant Badass: Mimi relates a story of Mary Anne's mother Alma running a water polo team out of a public pool when they were too disruptive.Mimi: Never again will a bunch of high school boys be so afraid of a pregnant woman and an old lady...Your mother always spoke her mind. Especially on behalf of those who can't stand up for themselves.
- Prone to Tears: Despite her serious nature, Mary Anne is actually very emotional. But she doesn't have the best coping mechanism, so she ends up doing this a lot.
- Reasonable Authority Figure: Played for laughs; Mary Anne's dad agrees to her changing her hair and clothes, but jokingly draws the line at getting rid of her wheeled bookbag, saying it's neccessary to prevent back problems.
- Right for the Wrong Reasons: The rest of the BSC points out Mary Anne's Extreme Doormat tendencies to her, but in a way that ends up reducing her to tears and inadvertently getting them in trouble for supposedly bullying her.
- She Is All Grown Up: By the end of the episode, Richard realizes that Mary Anne isn't a child anymore and agrees to some changes (hair, clothing) that let her feel more mature. When he sees her in her new outfit, he's clearly impressed by the difference in her attitude.
- So Proud of You: Richard tells Mary Anne this toward the end of the episode.
- Trans Tribulations: Halfway through her time babysitting Bailey, Mary Anne realizes she's a trans girl. When they later have to go to the hospital, it turns out Mrs. Dellvecchio hadn't updated Bailey's medical records yet, causing a nurse and a doctor to refer to Bailey as "he", something that obviously distresses her.
