Catia Roday has learned the hard way that love always disappoints, so when she finds herself falling for Josh, the handsome, charming, seemingly-perfect guy she just met on vacation - only to find out they hail from neighboring towns - she has one question: What's the catch?
Unwilling to let love make a fool of her again, Cat tries to ignore the chemistry between her and Josh, but it isn't easy when their vacation plans keep overlapping. With the universe constantly throwing them together, and her friends practically staging an intervention to tell her she's making a mistake, Cat decides to prove her point once and for all. On the way home, Cat makes a bet. She'll take her budding vacation romance back to the real world, and when she proves Josh is too good to be true, she wins!
What ensues is a series of tests and games with Josh one step ahead of her the whole time, until Cat realizes she might have just bet against the one man who can revive her faith in love. Worse yet, it turns out Josh isn't the gambling type.