An aimless young man who is scalping tickets, gambling and drinking, agrees to coach a Little League team from the Cabrini Green housing project in Chicago as a condition of getting a loan from a friend.

After a high-profile firing, everything is at stake for 40-year-old Jenna: her career, her ticking biological clock, and her bank account. Her fashion career comeback hits a snag when she falls for a charming, much younger coworker — who happens to be her boss’s son. As sparks fly, Jenna must decide if she’ll risk it all on a secret romance with the one person who could destroy her comeback.