Dawn's Big Date is the 50th book in the original series. The plot concerns Dawn's date with Logan's cousin Lewis, foreshadowed in #37 Dawn and the Older Boy. The subplot centers on problems with a new client, The Hills.
Synopsis (SPOILER WARNING)
The novel begins with Dawn and Mary Anne in the farmhouse, going over the menu for their New Year's Eve Party. Predictably, Dawn wants health food, while Mary Anne wants "those cute little hot dogs wrapped in biscuits." They decide to both make what they want, and decide which is better by who's food goes faster. Jeff is in Stoneybrook, visiting for winter vacation. Mary Anne reminds Dawn that Logan's cousin Lewis is coming to Stoneybrook soon, as his school in Louisville has a different break schedule then Stoneybrook.
The two girls wait for Sharon to get home from picking Jeff up at the Pike's house. Jeff helps Sharon find the coupons she misplaced - stuck on the underside of a plate in the microwave. The girls run to the store, and are a minute late to the BSC meeting. Kristy glares at Dawn, reminding the reader and Dawn that sometimes she is a little jealous of Dawn's relationship with Mary Anne.
At the meeting, the Baby-sitters Club receives a call from a new client - The Hills. They have a nine-year-old girl and a seven-year-old boy. Because this book is Dawn-centric, she gets the first crack at the new kids. She looks forward to the job, but first she has to attend the New Years Eve sleepover party that she is hosting with Mary Anne.
The sleepover party is the next afternoon, Saturday. Mary Anne and Dawn spend the afternoon cooking for their guests. Jeff helps Mary Anne make mini pizzas, Richard stays out of the kitchen, and Sharon arranges plastic-ware in paper cups. At seven p.m., guests start arriving. Mallory arrives first, with her brothers in tow. They run off with Jeff to do boy stuff. Kristy arrives with champagne and caviar for Richard and Sharon. Dawn tells Mallory what caviar is, which leads to a discussion of how adults like gross food. When Jessi arrives, her father joins Richard and Sharon in a toast. Then he drives home.
Stacey shows up at the party with a gift from her father — a tape called Cam Geary Sings, which is a tape of Cam Geary singing. None of the girls think much of his singing voice, except for Mary Anne, in a fit of loyalty to her favorite star. The girls continue with their sleepover, doing the stereotypical pre-teen girl thing — talking about boys. Kristy thinks that Pete Black still likes Stacey, Claudia thinks that Arthur Feingold is cute. Jessi reminds us that Quint has gorgeous eyes, and Mal, for some reason, thinks that Ben Hobart has a nice nose.
The girls give their resolutions. Kristy wants to make the Krushers into winners, clearing forgetting that they just won the "World Series" against Bart's Bashers. Mary Anne pledges to be less shy. Claudia wants to be better in school. Mallory wants to stop worrying about how her braces look, while Jessi resolves to do a ballotte. Stacey reminds everyone that she is diabetic by resolving to stop wishing she could eat food that she can't have. Dawn, being the narrator, tells us that she secretly wants to "get a boyfriend", but tells her friends that she promises to do something different with her hair for the new year.
Later, at the sleepover, all the girls except Dawn, Mallory, and Jessi, call boys to wish them a Happy New Year. Dawn feels like a baby, and yet again reminds us that she thinks guys don't see her as anything more then a good friend.
It snows when Dawn goes to sit for the Hills the next Friday. Sarah Hill answers the door, unaware that her parents had a baby-sitter coming. Harold Hill, the father, dashes out the door, unconcerned about emergency numbers or dinner. She compares Harold to Mr. Clean
Dawn gets to know Norman and Sarah. She finds out from Sarah that Norman is on a diet and he sneaks food. They catch him, and when Sarah starts to be mean to Norman, Dawn distracts her with The Little Mermaid. Later, Sarah goes to play with the next door neighbor, Elizabeth Yates, who calls Norman "Enormous Hill."
Later, Mary Anne gives Dawn a makeover and takes Dawn's picture. Dawn pouts in the picture, like a supermodel. This causes Dawn to rethink her attitude, and she puts on a new "cool" attitude to her friends and family. Mary Anne tells Dawn that Lewis will be arriving on January 30th. Dawn then mails Lewis a pouty picture along with a letter that says she can't wait to see him - something the old Dawn wouldn't have done.
Dawn chews gum for the first time, as part of her "new look". Mallory teaches Dawn how to blow a bubble in bubble gum at the BSC meeting. The rest of the sitters aren't so thrilled about "the new Dawn", and say it's not her. Dawn reacts, wondering why she's not allowed to be trendy. She feels that Mary Anne is the only loyal one.
Mary Anne fills Dawn's head with tips from magazines about dating, and Dawn tries really hard to keep "you directed conversation". It doesn't work, and she's embarrassed when she meets Lewis at the airport. He doesn't seem all that fond of her, because she's not herself.
Dawn, Lewis, Mary Anne, and Logan go to see Gone With the Wind. The date does not go well. Dawn blames Mary Anne, and Mary Anne blames Dawn. They have a fight, and involve the entire club by refusing to speak to each other at a BSC meeting.
Later, Dawn realizes that she isn't being herself, and that part of being an individual is not letting other people influence her so much. She convinces Lewis to go out with her again, realizes that he liked her better when she was herself, and later has a "first date" with him, where they start over.
Stacey, Claudia, and Jessi all sit for the Hills before Mary Anne helps Norman by telling him to stand up for himself. He does, and finally his parents stop pressuring him so much to lose weight, making him happier and less likely to binge eat.