Dating Dilemmas Books in Order

Chris Cannon's Dating Dilemmas books are sweet, funny companion romances about the moment when a crush stops being theoretical and starts wrecking a perfectly normal routine. The series is smaller and more self-contained than her dragon books, but it uses the same strengths: quick banter, likable awkwardness, and characters who have to sort out what they really want instead of what sounds good in their head. These are high school love stories with bookish energy and social pressure always lurking nearby.

The Dating Debate centers on Nina Barnes, who would be happy if Valentine's Day simply disappeared. She likes books, clear thinking, and not getting swept up in everyone else's couple drama. Then her mother moves them next door to West Smith, who is handsome, funny, and much more appealing than Nina wants to admit. The problem is that Nina values honesty, and West is carrying a major secret about his home life. Their chemistry is immediate, but the story keeps asking whether attraction is enough when one person is still hiding the truth.

99% Faking It follows Lisa, a crafty, book-loving nerd who is used to being the dependable friend instead of the girl at the center of the romance. Her plan is wonderfully ridiculous and very teen: fake-date her crush Matt so he can attract someone else, while she maybe benefits from the same borrowed attention. Of course the fake setup changes the way Matt sees her, which would be great if Lisa did not already feel the sting of being noticed only after someone else might want her. That turns the story into more than a light fake-dating comedy. It becomes a question of self-worth, timing, and whether Lisa is willing to accept less than being chosen first.

The setting across these books stays grounded in everyday teen life. There are neighbors, school friendships, shopping trips, awkward conversations, and a lot of moments where a supposedly smart plan turns into emotional chaos. Cannon also leans into fandom and reader humor, so the books have a friendly, slightly nerdy charm. They are romances, but they are also stories about how people explain themselves, hide parts of themselves, and sometimes talk themselves into the wrong thing.

That mix is the point.

Dating Dilemmas does not run on giant twists or sweeping melodrama. It runs on tension that feels familiar, liking the wrong person, misreading signals, worrying about secrets, and wondering whether love will make life easier or just more complicated. If you want sweet young adult romance with strong leads, clean emotional stakes, and a little snark, this series delivers exactly that.