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.
Over the anniversary party weekend, the plan goes awry in every way, and Josie must decide which direction her life – romantic and otherwise – is going to take.