Josie Mayfield, a no-nonsense businesswoman working at her father’s prosperous 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 Maxwell, 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: Maxwell 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, Maxwell stays with Josie as a guest in the Mayfield home, horrifying Joseph and Claire with his unsophisticated ways. Though things are rough and rocky at first, Maxwell soon begins to win over Joseph and Clair and they start to appreciate his carefree and spontaneous lifestyle. Maxwell’s presence even helps Josie’s insecure younger sister Mindy finally stand up for herself and inspires Josie’s grandfather (Conway) to pleasantly shock everyone by revealing a big secret. As Maxwell’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, Josie must decide which direction her life – romantic and otherwise – is going to take.