Problems Books in Order

The Problems series shows Brittainy Cherry in a lighter, more playful mode, though she still sneaks real emotion under the banter. These are small-town contemporary romances built around classic setups, fake dating, second chances, forced proximity, and the kind of chemistry that gets stronger the more the characters insist they are not interested.

The books are set in Honey Creek, Illinois, and that backdrop does a lot of the work. People know each other. Family history lingers. Work and personal life keep crashing together. That gives the romances warmth and comic friction, but it also lets Cherry explore how hard it can be to move forward when everyone remembers your past.

The Problem with Dating kicks things off with Yara and Alex Ramírez. She runs a dog business, he is the polished restaurant owner across the way, and a fake relationship arrangement puts two people with very different personalities into close orbit. It is the most openly rom-com entry, but it still has Cherry's interest in heartbreak, self-worth, and what dating looks like after being hurt.

The Problem with Players shifts into sports romance territory. Avery is a coach trying to keep her life in order when her ex, baseball star Nathan Pierce, becomes her assistant coach. Old attraction, old resentment, and a small-town setting make every interaction louder. It is a second-chance book with baseball in the background, but the real hook is two people trying to figure out whether they failed because they were too young, or because they were never built to last.

Then comes The Problem with Falling, which turns up the close-quarters tension.

That third book centers on free-spirited Willow Kingsley and a guarded man who likes his life quiet, simple, and protected. Summer cohabitation forces both of them to confront what they usually avoid. It fits neatly with the rest of the series, bright surface, deeper feelings underneath.

Read these when you want Cherry's emotional pull without quite as much devastation as Elements or the L&S books. The series still deals with fear, insecurity, and family baggage, but it wraps those themes in more humor, more flirtation, and a stronger small-town rom-com feel. Each book stands alone, though reading in order makes the family ties and returning side characters more fun.