The Holiday (2006)
Two women troubled with guy-problems (Cameron Diaz and Kate Winslet) swap homes in each other's countries, where they each meet a local guy (Jude Law and Jack Black) and fall in love. This movie has the charm of England, the stylishness of LA, and a sweet, nostalgic twist to make it anything but a typical romantic comedy. It’s full of heart and humor, and the interesting locales throughout will likely spark talk of what you should do for your next date.
Return to Me (2000)
Probably the best romantic movie ever made. A guy (David Duchovny) falls in love with a girl (Minnie Driver) who has just received his wife’s heart in a transplant operation. This premise could have been weird or corny, instead, Bonnie Hunt and Don Lake gave depth to every character in the film, from Grace’s uncle (Carol O’Connor) to her best friend’s husband (Jim Belushi). You care about these people, and they become as endearing as old friends by the end of this very sweet and romantic film.
Cousins (1989)
Larry Kozinski (Ted Danson) and Maria Hardy (Isabella Rossellini) are both married to other people, but when they attend the wedding of Maria’s mother to Larry’s uncle, they find themselves in the embarrassing situation of realizing their respective spouses (Sean Young and William Petersen) have just had a tryst right on the grounds where the wedding is held. Larry and Maria end up striking a friendship, and plot innocent yet effective tricks to get back at their partners. Before long Larry and Maria find themselves in love. This film reminds us that love always trumps sex.
There’s Something About Mary (1998)
It’s packed with tasteless jokes, is completely goofy, and has Brett Favre in his screen debut. What more could you ask of a film? This is a light comedy that will have you and your date laughing for hours even after you’ve seen it. Ben Stiller plays a guy hung up on his prom date, Mary (Cameron Diaz) and travels across country to find her. Stiller is the butt of every joke, but reminds us all that it’s the geek that gets the girl in the end.
The Laws of Attraction (2004)
Two New York City divorce lawyers (Julianne Moore and Pierce Brosnan) find love while defending opposing spouses in a divorce. The plot takes us from New York to Ireland and back again before these two meet, marry, and only then, fall in love. There is a key scene while the two characters are in Ireland that allow us to see how Brosnan has fallen in love with Moore for the very things she struggles with in her own personality (her fierceness often wrapped up in complete insecurity as one example). Francis Fisher as Moore’s mother adds the perfect touch to this delightfully unexpected lesson in compatibility.
