Charity Case Books in Order
Part ofPiper Rayne Books in OrderExplore the Charity Case books by Piper Rayne in order, with quick summaries, series background, and help following these connected Chicago romances.
Last updated: June 29, 2026
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Publication Order
4 books
Afternoon Delight
by Piper Rayne
2018
The one man this heroine cannot stop thinking about is the one who already broke her heart once, her ex-husband. Starting over would be easier if second chances did not feel so tempting.
Clean Slate
by Piper Rayne
2018
Before she moves back to Chicago, one woman has two painful goodbyes to make, one to the boss she is leaving, and one to the little girl she has grown close to. It is a short prequel about endings and fresh starts.
Happy Hour
by Piper Rayne
2018
Trying to rebuild is hard enough without falling for the man tied to your worst memories. For this heroine, that man is her ex-husband's divorce attorney, and he is far harder to hate than he should be.
Manic Monday
by Piper Rayne
2018
Back in Chicago after a divorce, a single mom swears off lawyers for good. Then Reed Warner, the best man from her wedding, keeps finding ways back into her life.
Series background & context
Charity Case is an early Piper Rayne series of connected contemporary romances set in Chicago. The books follow women who are trying to rebuild after messy personal upheaval, and that gives the whole series a slightly sharper emotional edge than some of the authors' more purely playful rom-com work.
These heroines are not starting from a calm place.
The setup begins with Clean Slate, a prequel that introduces a woman preparing to leave one life behind and head back to Chicago. From there, the main books move through a trio of romances built around old wounds, second chances, and the people who show up at exactly the wrong, or right, time. Manic Monday pairs a divorced mom with a charming lawyer who was the best man at her wedding. Afternoon Delight turns toward the man who broke the heroine's heart and became her ex-husband. Happy Hour raises the temperature again by putting a heroine face to face with the one man she hates even more than her ex, his divorce attorney.
What links the series is not just the city, but the sense that the characters are all trying to get their footing back. Careers, co-parenting, family obligations, and lingering anger all sit beside the romance. That gives the books a nice push and pull. The attraction is strong, but it never floats free of real-life complications.
Chicago matters here too. The books have that urban, busy, just-trying-to-keep-up energy, and the connected friend group helps keep the series feeling cohesive. Readers also get some crossover character links that later feed into other Piper Rayne worlds.
If you want romances where love shows up right in the middle of legal drama, divorce fallout, and hard-earned fresh starts, Charity Case is worth a look. It is funny in places, but it also knows that starting over can be messy work.
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