Colin, who has a gift for trivia and word games, just graduated from high school, only to have his girlfriend Katherine dump him. No surprise. Colin's been dumped a record 19 times now - all by girlfriends named Katherine! In a funk, he let's his best friend Hassan talk him into a good, old-fashion road trip, while Colin works on the ultimate mathematical formula to predict how long his romatic relations will really last. Their adventures quickly lead them to a tiny speck on map, Gunshot, Tennessee, where they meet Lindsey, a local tour guide. Her mom hires Colin and Hassan to help record the personal histories of the local townfolk. And between their many hilarious adventures Lindsey works with Colin to help create his ultimate dating theorum!