In this film set in Los Angeles, the plot revolves around Emily Tyler (Ashley Olsen), who enjoys surfing, and her twin sister, Tess (Mary-Kate Olsen), a member of a high-diving team, who try various stratagems to get a girlfriend for their widowed dad, Max, a talented artist and sculptor. After all their attempts end in failure, Tess and Emily -– with a little help from their friend, Cody (who has an obvious crush on Tess) –- decide to paint an advertisement on a giant billboard situated high above Sunset Boulevard.
A woman named Brooke Anders answers the ad, and she and Max come to like each other and start dating. At first, Tess and Emily don't like Brooke's son Ryan, but when he helps foil an elaborate scheme by Max's business manager, Nigel, to break up the romantic relationship between Max and Brooke (Nigel thinks Max's work will suffer as a result), the girls eventually accept Ryan.
Some have seen the film as a modern retelling of Shakespeare's The Merchant of Venice, mostly because at the end of the film, every character is satisfied and happy, except, of course, for the villainous minority character.
- Tomboy and Girly Girl - Mary-Kate Olsen plays Tess Tyler, a girl who likes to cook and is the best member of the high diving team. She says it's the next best thing to the ballerina that their mom was. Ashley plays her boy-crazy twin sister, Emily, who enjoys surfing.