Families who loved My Best Friend's Boyfriend by Mary-Kate Olsen often look for books with a similar feel. These 20 recommendations were selected for their similarity in style, theme, and reading level.

A parent would reach for this book when their pre-teen is beginning to navigate the complicated social hierarchies of middle school and the first stirrings of romantic interest. It specifically addresses the 'friendship first' dilemma that occurs when a child feels a crush on someone their best friend is already dating or interested in. The story follows Riley and Chloe Carlson as they balance school, family, and the social minefields of teenage life. While the tone is light and humorous, it provides a safe space to discuss loyalty, the ethics of 'calling dibs' on a crush, and the guilt that comes with secret feelings. It is an ideal choice for parents looking to normalize the confusing emotions of early adolescence without the content becoming too mature or heavy.