Dummy

Steven Schoichet (Adrien Brody) is, possibly, even more socially-retarded than I am, and the only way he manages to overcome his anxiety is by living vicariously through...his ventriloquist dummy. Steven falls head-over-heels in love with Lorena Fanchetti (Vera Farmiga), but finds himself only able to interact with her through his nameless dummy.

Can't Buy Me Love

Ronald Miller (Patrick Dempsey) is a high school nerd who manages to convince Cindy Mancini (Amanda Peterson) to prostitute herself to him for a month, but never once manages to get laid out of the situation. Someone's doing it wrong.

The Holiday

The Holiday features the related (though, fortunately, untangled) romances of Amanda Woods (Cameron Diaz) and Graham Simpkins (Jude Law) as well as Iris Simpkins (Kate Winslet) and Miles Dumont (Jack Black). Both romances are unlikely, due to the strange situation presented, but somehow...believable and satisfying.

While You Were Sleeping

This is the love story of Lucy (Sandra Bullock) and Peter (Peter Gallagher). It's also the love story of Lucy and Jack (Bill Pullman), Peter's brother. Actually, it's the love story of Lucy and Peter's entire family. Oh, and Ashley (Ally Walker) is thrown into the mix as Peter's actual fiancée.

Sixteen Candles

The budding love story of Samantha Baker (Molly Ringwald) and Jake Ryan (Michael Schoeffling) cannot be properly told without mentioning the intertwining romance of Caroline Mulford (Haviland Morris) and Ted (Anthony Michael Hall). Also worth mentioning are the romance between Jake and Caroline, and the numerous passes that Ted makes toward Sam.