Alan Gray is an eighth-grade student at Stoneybrook Middle School. He is known as a pest and class clown. He and Kristy have a long-time rivalry. He's been bothering Kristy since at least fifth grade, when Kristy became the first person to have pranked him back, tempting him into stealing a sandwich full of fake flies.
In #2 Claudia and the Phantom Phone Calls, Alan, along with Trevor Sandbourne, stole the Baby-sitters Club record book and made several calls to houses where Kristy was baby-sitting in an attempt to ask her to a dance. She accepted, although the date seemed to have no lasting impact on their relationship, which is primarily pest and pest-ee. For example, in a representative scene in book #10 (Logan Likes Mary Anne!), Kristy loudly complains when Alan puts M&M's on his eyes and calls himself Little Orphan Annie.
In #55 Jessi's Gold Medal, Kristy and Alan had a footrace, agreeing that the loser would be the winner's slave for a week. Kristy won.
In the Friends Forever series, Alan is presented as a serious candidate for Claudia's affections.