Ainslie Logan is the worst waitress in the world. A displaced, former trophy wife from the south, she's barely supporting herself and her three children working as a waitress in a popular sports bar north of Boston. Dave Mason is a high school principal who spends a lot of time in that local watering hole.
Due to Ainslie's lack of skill, Dave’s more than once ended up wearing his meal instead of eating it. She’s not his favorite person; she thinks he's a stuck-up jerk with an attitude. When her kids come to his attention during some bullying problems, he changes his opinion pretty quickly when he sees what a great mom she is.
Dave has been waiting for the one woman he can fall in love with and that woman is Ainslie. Ainslie is cautious, due to her rat fink, stinker ,jailbird of an ex-husband. She also has her children to consider, who are having problems adjusting. So while she’s very attracted to Dave, she fights falling in love with him.
When Dave pulls out all the stops to woo and win over Ainslie (and her kids) in a way that would make Cinderella swoon, she learns that yes, she can love again.