Ned Fleming is a rather conservative businessman who owns Fleming Co., a once successful printing business. Leaving his struggling business behind, he and his wife Barb, along with their 15-year-old son Scotty, travel from Grand Rapids, Michigan to visit their oldest daughter Stephanie, who is studying at Stanford University. While there, they are introduced to Stephanie's self-made billionaire boyfriend, Laird Mayhew, who is a famous internet entrepreneur.
Laird's vulgar, gregarious, and blunt personality is slightly arousing for Barb and Scott, but causes Ned to downright despise him. Stephanie insists that he is a nice person, and that he makes her happy. But when Laird reveals to Ned he plans to propose to Stephanie in only five days, the race to prove himself worthy of her love so Ned can give them his blessing begins, with business problems arising throughout.
Laird goes out of his way to win over Barb and Scott, while Ned schemes to make sure Laird goes down in flames.