Big-hearted cowboy Josh Wooster decides to play matchmaker when his former high school sweetheart returns to town. Enlisting the aid of long-time friend Rachel, he tries to set up his old girlfriend with the new guy in town. But Cupid has his own ideas where love is concerned, and Josh doesn't see the arrow aimed at his heart until it's too late to sidestep it.

Rachel Addison would do anything for Josh, whom she's had a crush on forever. Watching Josh fall for his former girlfriend all over again would be too much to bear, however. It's time to rope him in or cut him lose. Which will Josh prefer?