Dempsey Solomon

Dempsey Solomon is a friend and crush of Layne's. When he was an considered a "loser", he was called "Humpty Dempsey" by Massie because he was overweight. Over the summer, he and his parents went to Africa to help rebuild houses, during which he lost weight and got a tan. Massie crushes on him in book 9, despite the rules of her own "boyfast". Claire uses him to "jealousy-flirt" so she can get Cam Fisher back, again despite the boyfast. He was the role model for the LBR guys in the overflow trailers when Massie was giving them make-overs. At the end, Massie ends up liking him so much that she ends her own "boyfast". In P.S I Loathe You, both Layne (Kristen's Secret Best Friend) and Massie ask Kristen to find out who he likes, as they are neighbors. Dempsey reveals that he likes Kristen, and in Boys R Us, they begin to date. He ends up joining the soccer team and befriends his team members. In These Boots Are Made For Stalking they (sort of) break up, though in 'A Tale Of Two Pretties', Dempsey visits Kristen at Christmas, in which she is very glad to see him, implying they still like each other.