An awkward accountant hires a dating coach who also happens to be his old teenage crush. He gets a date with a pretty woman he has had his sights on for some time, but realizes they are incompatible. Meanwhile, his dating lessons with his crush/coach reawaken old feelings. Not realizing the feelings are mutual, he finds himself unable to act on them due to his fear of being rejected by the one he truly loves.

Mary is a young dancer who meets Joey at a high school masked ball. They dance together and fall in love. While Mary rushes out of the ball, she drops her iPod. Joey, not knowing who Mary really, uses the iPod to find her.