Troublemaker Books in Order

The Troublemaker books lean into one of Cassie Mae's favorite ideas: love gets messy the minute someone decides to fix their life with a terrible plan. These are contemporary romances with bright banter, strong chemistry, and characters who look like opposites on paper but make a strange kind of sense together. The stories are connected by recurring people and a shared everyday-life feel, so the series reads best in order even though each couple gets its own ending.

I Knew You Were Trouble sets the tone. The heroine wants the whole falling-in-love package, but the guy she wants looks all wrong for the part. Her answer is not to step back. Naturally. She takes lessons in being bad from tattooed, motorcycle-riding Pete, and the book gets its spark from watching a good girl try to force herself into a role that does not fit. It has a playful, modern Grease flavor, but it stays grounded in work, class differences, and the simple fact that attraction rarely follows a sensible plan.

Bad ideas are the engine here.

Double Trouble widens the world by focusing on Maddie and Tanner. Maddie is chasing a skateboarding sponsorship and has no patience for distraction. Tanner is the kind of guy who hangs back, misses his chance, and then quietly shows up anyway. Their story adds a nice layer to the series because it brings in adult worries about rent, work, and ambition without losing the sweetness and humor that make the line feel like Cassie Mae.

What links the books is not high drama or a giant mystery arc. It is community. Siblings, coworkers, friends, and familiar faces keep popping in, so the romances feel like part of the same neighborhood. There is also a strong undercurrent of ordinary people trying to build stable lives while still making room for love, which gives the books a little more weight than the goofy setups first suggest.

If you like rom-coms where people flirt, argue, overcommit, and then accidentally get honest, Troublemaker is a good fit. Expect charm, chaos, and characters who keep insisting they know what they are doing right up until the moment they clearly do not.