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!!

An awkward accountant hires a dating coach who also happens to be his old teenage crush. He gets a date with a pretty woman he has had his sights on for some time, but realizes they are incompatible. Meanwhile, his dating lessons with his crush/coach reawaken old feelings. Not realizing the feelings are mutual, he finds himself unable to act on them due to his fear of being rejected by the one he truly loves.