Fourteen-year-old Win Kelly has just moved to Santa Fe with his single mom and his seven-year-old half-brother Donny. His mom signs the boys up for Los Amigos, a program that pairs fatherless boys with men who can act as a Parental Substitute. Win is paired with Elliott Deerfield, a bachelor who likes opera, gourmet cooking, and good grammar, and who Win's Only Friend Paul Crowser is convinced is a homosexual. At first Win plans to request a different amigo as soon as the six-week trial period ends, but he soon grows to like and respect Elliott.
Elliott & Win contains examples of:
- Ambiguously Gay: Paul is convinced Elliott is gay because of his confirmed bachelor status, his fashion sense, and his interest in art, cooking, and opera. Win never learns for sure if he is, and eventually he decides that Elliott's sexual orientation is none of his business.
- D-Cup Distress: Win's new friend Heather Key has huge breasts, which give her backaches and attract all sorts of bad attention, despite her efforts to hide them in baggy shirts. Boys and girls alike assume she's a tramp, and Paul's sister Vanessa calls her a cow and makes mooing noises at her. She has breast reduction surgery planned, and is counting the days.
- Dedication: To My Friend George
- Disappeared Dad:
- Win's dad was a guy named Michael X. Kelly. After Win was born, Michael became a truck driver who was away from home a lot, causing him and his wife to drift apart. Now he lives in San Diego with his new family. Win hasn't seen him in seven years. He got a letter from his dad four years ago, promising to take him to the zoo and the beach, but nothing ever came of that.
- Donny is the product of their mom's second marriage to Bobby Don Willett, who also has a new wife (his third) and a family.
- Paul's dad lives in Dallas. His mom says that he's a terrible man, although she won't specify what he did, and made him promise to stay out of Paul's life. She is dismayed when Paul's dad invites him to visit him in Dallas, and Paul insists on accepting. He's not really a bad guy, just gay. Paul swears off all contact with him upon finding out.
- After Heather's rape, her mother makes her father move out on the grounds that he's male and an oppressor.
- Famous Ancestor: Heather is distantly descended from Francis Scott Key, which is why her dad's bakery is called the Star-Spangled Cookie.
- Foolish Sibling, Responsible Sibling: Ma's parents see her this way. Her brother is a lawyer and her sister is a "proper suburban matron," while she was a rebel who was sent to boarding school for not behaving, ran away, and hitchhiked to California in The '60s. Ma's only regret is her lack of a college education, but her parents see her as having wasted her life.Win: Did you throw your life away?
Ma: By their standards I did. - Grammar Nazi: Elliott is always correcting Win's grammar. When Win says, "I don't want no more," Elliott serves him a large helping of chicken salad because he used a double negative.
- How Dad Met Mom: Win's parents met on a hippie commune in Oregon, where they smoked lots of pot.
- It's All My Fault: Win blames himself for Heather's brutal gang rape because he took her to the blockhouse at night, which Ma always warned him against, and he didn't fight back against the rapists. Elliott tells him that he made a simple error in judgment and that he couldn't have defended Heather from four men, and suggests that he see a counselor.
- Narrative Profanity Filter: Win listens to Donny swear in his sleep. "He used words Ma would have had a fit over, and I don't mean 'friggin' and 'craperoo.'"
- Only Known by Their Nickname: Win was named after Winston Cigarettes because his dad was trying to quit smoking when he was born. He understandably prefers his nickname.
- Parent with New Paramour: After Ma broke up with her third husband, Joe Favello, she swore off men forever. But in Santa Fe, she falls in love with Donny's amigo, Hal Norris. Before long, the two are planning to get married. Win is sure she's in for another painful divorce.
- Secret Diary: Win has a notebook that was originally labelled "The Private Thoughts of Win Kelly." When Donny couldn't resist snooping, Win renamed it to "Spelling and Grammar Exercises."
- Struggling Single Mother: Win's mom works three jobs and still finds time to go to school. Win has to do a lot of housework for himself.
- Trademark Favorite Food: Donny's main source of nutrition is flufferbanutter sandwiches, made with marshmallow fluff, bananas, and peanut butter.
