An accountant, who never quite grew out of his awkward teenage years, finds himself with a dating coach - she happens to be his high school crush as well. Thanks to his coach, he gets a pretty woman he has his sights on for some time, but realizes they are incompatible. Meanwhile, his dating lessons with his teenage crush 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.

Nick is a successful young man whose comfortable West Coast life couldn't be better. However, when his girlfriend falls under the influence of lecherous music producer Lenny Swackhammer, Nick impulsively decides to travel to Toronto to intervene. Nick's buddies Tyler and Dime opt to turn the quest into a cross-country road trip that's complete with wacky antics and encounters with beautiful women.