Unwilling to let love make a fool of her again, Cat tries desperately 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 huge mistake, she decides to prove her point once and for all. On the way home, she 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! (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 the friendly wager has her betting against the one man who may be able to revive her faith in love. Worse yet, it turns out Josh might not be the gambling type.