People have called me impulsive and reckless before, yet my spur of the moment decision to "date" Claire Hart might be the best chance I've ever taken. When I find out my landlord is selling my house, I'm desperate to buy it. But as a second grade teacher, I'm not exactly rolling in the dough. I find my solution in a local radio station giving away $10,000 dollars. The catch? Only couples can enter. Undeterred, I convince the school librarian to play my girlfriend, although she doesn't think anyone would believe we'd ever date in real life. Especially since she was recently dumped for supposedly being boring and grumpy. One kiss is all it takes for me to know there is nothing boring or grumpy about her, and suddenly this little game we're playing is about more than just money. I am nothing if not competitive, and Claire is one challenge I'm not willing to lose.