Though there are countless films that focus on troubled love, waning love, or downright dysfunctional love, this list of films is comprised of love stories that are pretty much one-sided. The unrequited narrative is not nearly as common in mainstream Hollywood. Audiences are typically force-fed, and therefore expect, the happy, romantic endings. While there’s nothing inherently wrong with this, it’s always nice to have some diversity and balance in mainstream Hollywood films.
5) My Best Friend’s Wedding (1997), dir. by P.J. Hogan
My Best Friend’s Wedding has all the makings of a typical Hollywood rom-com. Julianne (Julia Roberts) finds out her best friend Michael (Dermot Mulroney) is getting married. They had a pact that if they didn’t get engaged by the time they were both thirty years old, they would marry each other. When she learns he found someone—at age thirty—whereas she has not, she sets out to win him over and destroy his engagement to Kim (Cameron Diaz). What is so intriguing about this film is that Julianne does not succeed. She doesn’t “get the guy” at the end. Rather, she realizes Michael does truly love Kim, and finally lets them be. Though her “love” for Michael may have come out of her own insecurities and jealousy at first, she does grow to genuinely fall in love with him, while he remains interested only in friendship.
4) Almost Famous (2000), dir. by Cameron Crowe
Taking place in the ‘70s, young teen William (Patrick Fugit) gets an incredible opportunity to tour with and cover the up-and-coming band Stillwater for Rolling Stone Magazine. He spends most of the tour desperately trying to interview the band members to no avail. Be it fights among the band, drugs, alcohol, or all of the above, they continually brush him off. Meanwhile, he gets closer and closer with the “Band Aids” (a more respected term for groupies) that follow the band on tour. Mostly the beautiful “Penny Lane” (played by Kate Hudson in her prime). Although there is not much of an age difference between Penny and William, Penny’s life experience and seasoned sexuality put her far beyond William. She’s treated terribly by band member Russell (Billy Crudup), but she remains utterly infatuated with him. Meanwhile William falls hopelessly in love with Penny, and seems to want nothing more than to be with her. Between William’s longing looks at Penny and his saving her life after an overdose, the relationship between the two is pretty heartbreaking.
3) Pretty in Pink (1986), dir. by Howard Deutch
I have spent many, many years filled with deep resentment towards the ending of Pretty in Pink. High school outcast Andie (Molly Ringwald) struggles to make ends meet living just with her deadbeat dad. Her childhood sweetheart, Duckie (Jon Cryer) and rich playboy Blane (Andrew McCarthy) simultaneously woo her. The original ending of the film (as written by the incomparable John Hughes) had Andie ending up with Duckie. Test audiences hated it. Molly Ringwald apparently hated it (she felt Duckie was more of a brother figure). In fact, it was this film that ended John Hughes’s and Molly Ringwald’s working relationship. Every time I watch this movie, I pray for Andie to choose Duckie. He’s so lovable, so sweet, so cute…and you have to remember this was far before the ill-fated “Two and a Half Men.” Not to mention that Duckie’s deep, undying love for Andie is just tragic. I defy you to watch the above clip of Duckie lip-syncing to Otis Redding and not fall hopelessly in love with him.
2) Jules et Jim (1962), dir. by François Truffaut
Taking place in Paris before WWI, two friends (one Austrian, one French) fall in love with the same woman. Although each gets their time with Catherine (Jeanne Moreau), it becomes clear that she is never fully committed to, or truly in love with, either Jules (Oskar Werner) or Jim (Henri Serre). She starts by marrying Jules, then post-war, “falls in love” with Jim. Her behavior is often erratic but undeniably charismatic. Each man spends a lengthy time pining over Catherine with no little reciprocation at any given moment. And when she does show affection for either, it’s clear that it’s shallow and fleeting.
1) The Rules of Attraction (2002), dir. by Roger Avary
The entire premise of Rules is unrequited love. Multiple narratives of college students are woven together, and not one person is with the one they want. In fact, every character that desires someone else isn’t in any way interested in those interested in them. Sean Batemen (played by James Van Der Beek), the younger brother of American Psycho’s Patrick Bateman, falls for Lauren (Shannyn Sossamon). Lauren is in love with Victor (Kip Pardue), who is on a sexual escapade across Europe. Paul (Ian Somerhalder) is in love with Sean. And Sean receives countless love notes from a secret admirer he hopes is Lauren. It’s a depraved love triangle, that leaves everyone depressed, alone, and bitter.
Honorable Mentions: Law of Desire (1987), 500 Days of Summer (2009), Audition (1999), Casablanca (1942), Forrest Gump (1994), The Double (2013), Brokeback Mountain (2005).
Author: Catherine Haas
Catherine Haas is a native Philadelphian who received her master’s in film history from Columbia University. She is a freelance film programmer, writer, and an avid pug enthusiast.