Todd is at the pinnacle of his game; a great job, great friends and more women than he knows what to do with. He owns a lounge that frequents some of the finest women and talent mid-town Chicago has to offer. Unsatisfied with his level of romantic achievements, he goes on a quest to date three women at one time. He believes the laughable exhaustion of just keeping his story straight is his only penance to pay until he finds out that all three women share a common bond and the aftermath is more than he bargained for.

As four friends prepare for life after high school, different challenges bring about turning points in each of their lives. The dramas unfold and resolve at their local rollerskating rink, Cascade.