Ella, a woman turning 40, lets Tyler, a 26-year-old guy she meets at her stepfather's wake, believe she is only turning 30. Meanwhile, she runs into an ex from high school (played by Major League Baseball pitcher Adam Wainwright of the Cardinals) and her well-meaning mother Naomi pushes for a future with Dr. Gordon. It's a lot for a woman who is content with the single life back in Chicago.