Tom, an artist, has been burned by love too many times. His girlfriends keep leaving him for rich men! In frustration, he and his unemployed friends hatch up a hilarious scheme to meet and marry ultra rich women. Trouble is, they are going broke keeping up appearances and must borrow from a loan shark who threatens bodily harm if the loan is not repaid within a month. This means they must go after wealthy women, and fast!!

Over the holidays, Ned, an overprotective but loving dad and his family visit his daughter at Stanford, where he meets his biggest nightmare: her well-meaning but socially awkward Silicon Valley billionaire boyfriend, Laird. The rivalry develops, and Ned's panic level goes through the roof when he finds himself lost in this glamorous high-tech world and learns that Laird is about to pop the question.