Plot Synopsis

Josie Mayfield, a no-nonsense businesswoman working at her father's successful cookware company, thinks her boyfriend Richard is the perfect man -- handsome, successful and driven. The problem is that her parents, Joseph and Claire, do not agree. When she meets up with Gridley, an underachieving, old high school flame (who still has a crush on her), Richard cooks up a plan to make himself look good to her parents: Gridley will be her date at her parents' upcoming anniversary party. When they see her with a "loser," they'll give anything to have him back in the picture. Over the anniversary party weekend, Gridley stays with Josie as a guest in the Mayfield home, horrifying them with his unsophisticated ways. Though things are rough and rocky at first, he soon begins to win them over and they start to appreciate his carefree and spontaneous lifestyle. His presence even helps Josie's insecure younger sister Mindy finally stand up for herself and inspires Josie's grandfather to pleasantly shock everyone by revealing a big secret. As Gridley's visit loosens up the previously stiff and uptight Mayfield family, Josie starts to fall for him and realizes she hasn't been living her life for herself. When Richard shows up at the house, she must decide which direction her life -- romantic and otherwise -- is going to take.