Trouble With... Books in Order

The Trouble With... books follow Holly as her family keeps changing around her. In The Trouble with Cats, she is dealing with her mother's remarriage, a new house, a new school, and four cats that seem determined to make every day harder. By the next books, Holly is in a new San Francisco neighborhood, making friends, meeting babies, and eventually helping plan a birthday party for her twin little brothers. The problems are ordinary on paper, but Freeman understands how enormous they can feel when you are the child living through them.

These are family stories first, with comedy running alongside the stress.

Holly is a good guide because she is practical, observant, and not endlessly cheerful. She gets annoyed. She worries. She tries to be helpful and sometimes makes things messier. That keeps the books grounded. The cats are funny, the babies are sticky, and the twins are chaos machines, but the series never loses sight of the deeper question underneath all the title trouble: how do you make room in your life for a family that is still rearranging itself?

The later books widen Holly's world in smart ways. In The Trouble with Babies, she meets Xavier and Annie while learning a new neighborhood and adjusting to another family surprise. In The Trouble with Twins, those same friendships help carry a science-themed birthday plan through the usual disasters of small children, tired adults, and last-minute improvising. Freeman also gives young readers a broad picture of family life. Stepparents, siblings, neighbors, and different kinds of households are all treated as normal parts of the world Holly moves through.

The emotional stakes stay gentle, but they are never trivial.

These books sit in that sweet spot between easy readers and longer middle grade novels. The chapters are short, the humor is easy to follow, and the conflicts come from real life rather than villains or magic. That makes the series especially good for younger readers who want recognizable problems, strong characters, and satisfying endings. If you start with The Trouble with Cats, you get to watch Holly grow into her changing life one problem at a time, which is really the whole point of the series.