The last time Catia Roday fell in love, it cost her everything. She’s learned a lot since then, though—specifically, men always disappoint. When she meets handsome, sweet, seemingly-perfect Josh Rideout on a far-off beach vacation, only to find out they hail from neighboring towns, she has one question: what’s the catch?
Her friends have practically staged an intervention to tell her she's making a huge mistake, so on the way home, she makes them a bet. She’ll keep seeing Josh after the vacation ends and when he proves he isn’t as perfect as he seems, she wins! And she avoids another heartbreak.
What ensues is a series of tests and games with Josh one step ahead of her the whole time, until Cat realizes she may have just bet against the greatest love of her life. Worse yet, it turns out Josh isn't the gambling type.