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 Josie’s parents, Joseph and Claire, do not agree. When Josie meets up with Gridley, an underachieving, old high school flame (who still has a crush on Josie), Richard dreams up a plan to make himself look good to Josie’s parents: Gridley will be Josie’s date at Joseph and Claire’s upcoming anniversary party. When Joseph and Claire see Josie with a “loser,” they’ll give anything to have Richard back in the picture. At least, that’s the plan.