Al Connelly (Freddie Prinz Jr.) and Imogen (Julia Stiles) are a young couple whose passionate romance takes them for a ride down the all-too-powerful path of first love.

Set against the chaotic and hilarious backdrop of college lifestyle in New York City, their story brings to light the ever-present conflict between true love and the temptation to wander astray from commitment. When mischievous friends enter the scene, Al and Imogen are confronted with obstacles that add to the highlights and pitfalls of their love affair. Ultimately, their journey allows them to face the future, with some unexpected results.