After one too many cocktails in the wake of a break-up, romance writer Gracie Landing emails her old high-school crush, Colin Yarmouth, receiving a surprising response.
The two forge an unlikely friendship as Colin's tales of his own break-up become an unexpected source of material for Gracie's current work-in-progress, a project with the potential for a hefty advance that could launch her out of near-poverty.
With the deadline looming and her checking account dwindling, Gracie hastily uses Colin's stories without considering whether there could be any personal overlap with other "characters" in his life.
In the mayhem that ensues, she risks her entire career, along with the chance at her own happily-ever-after.
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