That Boy (Damon + Ainsley) Books in Order

The Damon and Ainsley books take the That Boy world into its next-generation era. These stories still have the family warmth and football-threaded atmosphere of the original series, but the tone skews a little older, with summer attraction, college pressure, and the kind of choices that can change several futures at once.

Damon knows what he wants early.

Ainsley is harder to convince. That is part of the fun. Their story begins with a crush that has been quietly building for years, then tips into something much more serious once time, age, and circumstances shift. A summer setting helps, because Dodd is very good at making lake trips, vacations, and family overlap feel like both a comfort zone and a trap. Everyone is close enough to matter. No one gets much privacy.

What separates this branch from the original That Boy books is the stage of life. Damon is chasing football dreams. Ainsley is trying to protect her own future while figuring out whether love can fit inside it. Their books are less about choosing between two boys and more about timing, responsibility, and whether a relationship can survive when real life arrives faster than expected.

Even so, the appeal is familiar. These are romances built on history, chemistry, teasing, and the sense that family connections make every feeling bigger. If you liked the cozy pull of the That Boy universe and want the newer couple with higher stakes and a more mature edge, Damon and Ainsley are the natural next read.