Derrick Harrington, dubbed as Derrington by The Pretty Committee, is the Briarwood Boys alpha. Derrington is known to play as the goalie for his soccer team, the Tomahawks. He plays Massie Block's love interest throughout the novels, but then becomes Dylan's boyfriend in P.S. I Loathe You. Dylan tries to keep it a secret but he doesn't like it or understand it. She can't make it official untill Massie releases him from her hold, aka splashing water on him (her hold is spraying Chanel No. 19 perfume on him).
Derrington is the goalie for the soccer team. He is known for his famous butt wiggle; he pulls down his shorts and moons the crowd. He calls most people by their last names (He calls Massie "Block"), and has a sense of humor. He is an alpha, and his friends include Cam Fisher, Josh Hotz, Kemp Hurley, and Chris Plovert. In It's Not Easy Being Mean, Derrington has a very messy room, but he cleaned it up just for Massie. Derrington has a kind heart.
Derrington is described to look like a yellow lab. He has shaggy blond hair and large brown eyes. He wears shorts throughout the seventh grade, when he loses a bet, and starts wearing jeans in the eighth grade.
Derrington has a sister named Sammi and a housekeeper named Mini. Derrington has a kind heart.
Derrington has a crush on Massie from Best Friends for Never.
In Revenge of the Wannabes, Massie's and Derrington's relationship is foreshadowed.
In Invasion of the Boy Snatchers, Nina Callas convinces Massie that Derrington likes her (Nina) instead of Massie. This causes Massie to go to the dance alone, and Massie ignores him. When Nina's fraud Spanish soccer spell is revealed, Derrington and Massie make up. Massie gives Derrington her "M" brooch, which Derrington wears on his shorts. He says that he'll wear it all the time. Derrington gives Massie the cutest couple award, to make up for him ignoring her.
In The Pretty Committee Strikes Back, Massie teaches people how to kiss in her kissing clinic called MUCK. This leads Derrington to believe that Massie has been kissing someone else, due to the fact that she's never kissed him before. Derrington throws his "M" brooch onto the ground, and dumps Massie. Then, Massie confronts him and apologizes. She forcefully kisses him, and they make up.
In Dial L for Loser, Derrington goes to the dance with the words "I'm with Massie" painted across his chest because Massie couldn't go.
In It's Not Easy Being Mean, Massie discovers Derrington's filthy room and becomes disgusted. Derrington cleans it up just for Massie, and she likes him again.
In Sealed with a Diss, Derrington says on ESP that he has an "issue" with Massie. At Skye Hamilton's party, Derrington sees Massie and Chris Abeley together. He dumps Massie and throws away the soccer earrings that he got for her. Then, Derrington confronts Massie and tells her that he thinks that she's immature. He leaves the party, thinking that Massie cheated on him, which is not true.
In Bratfest at Tiffany's, Derrington changes his style, and wears jeans for the first time ever. Even though this happens, Massie's become interested in someone new and has sworn off boys.
In P.S. I Loathe You, Derrington and Dylan Marvil start getting along really well and in one detention they had together he tells her he likes red hair, is a fan of the Jonas Brothers, the reason why he wore shorts throughout 7th grade (he had lost a bet), and doesn't like being called Derrington. After she helps him pick out a present for his sister's birthday, they start liking each other. At a soccer game they kiss and start seeing each other behind Massie's back, mostly in detention. Finally, Dylan confronts Massie and asks her to release the hold she has on Derrick (she had sprayed him with Chanel No. 19, which made him hers. To release her hold, Massie needs to pour water on the person she sprayed). Massie gets mad and releases the hold on both Dylan and Derrick by pushing them both into the pool.
In These Boots Are Made For Stalking, due to the upgrade, Dylan breaks it off with him, also because she became disgusted with him after he lost another bet, and now has to wear his clothes backwards for a year.
It's implied in the last book that Derrington may still have feelings for Massie.