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Great Lesbian Date Movies: Heartbreakers

Updated on July 18, 2007

WRITTEN BY: Jaclyn Popola

In the land of Hugh Grant and Sandra Bullock, "tearjerkers" or "heartbreakers" are defined as films, usually of the romantic genre, which prompt one to cry their eyes out over the tragedy of love gone wrong -- before, of course, both parties reunite just in time for a happy ending. For the purposes of this hub, however, I'm going to be talking about REAL tearjerkers, the movies that make you cry because you're so depressed you can't do anything but weep. I'm not trying to be melancholy or morbid though. On the contrary, films of this nature teach extremely valuable lessons. They teach us to appreciate what we have in the exact moment we have it. The endings may be sad, but movies of this type make you realize just how quickly love can go, and remind you to never take anything for granted. Live the moment now, children, ‘cause you can't live it once you're dead.


Radha Mitchell plays "Syd", an editor at a haughty-taughty art magazine who meets Lucy (played by Ally Sheedy) who is---gasp!---a once renowned but now out of work photographer. What are the odds? Anyway, their relationship unfolds fairly effortlessly, except for the fact that Syd has a boyfriend who she's pretty serious with, and Lucy has a girlfriend and a heroin habit that's pretty serious with her. On Syd's encouragement, Lucy gets back into taking pictures and the two head upstate for a weekend retreat on "business" so Lucy can find some inspiration. A few days prior to this, Syd does a line of heroin with her, and you begin to think that will be the plot of the story (she gets sucked into the hell of addiction to be closer to Lucy). Instead, on their drive upstate, Lucy literally throws her addiction out the window for Syd when she tosses her stash after Syd says, "I don't want to be with you like that." It's hard to explain why this movie earns it's tearjerker status without giving away the ending, so let's just say it's heartbreaking because Lucy, at the urging of her now-ex-girlfriend, Greta, ends up taking one more hit of heroin when she returns from her and Syd's weekend of lovemaking.

  • Lucy's mother: What did you do to yourself? C'mon, tell me! What kind of problem?
  • Lucy: I don't know. It's not really a problem. It's more of an issue.
  • Lucy's mother: You just said a problem. Is it a problem? Now it's an issue. Is it a problem or an issue?
  • Lucy: Both. I have a love issue, and a drug problem. Or maybe I have a love problem, and a drug issue. I don't know.


If Angelina Jolie wasn't a sex symbol before this film debuted in 1998, she certainly became one after it's release. Based on the true story of a famous fashion model from the late 1970s, Angelina plays wild Gia Marie Carangi in this biography that follows her life from age 17 until her death from AIDS in 1986. I wish I could say that she spent her short time on earth living life to the fullest and inspiring millions. Unfortunately, her young life was peppered with heartache, and although she quickly became a very successful model, the spotlight introduced her to narcotics that would never release their grasp on her life. Earns it's Tearjerker Status Because: Gia dies of AIDS, which she contracted from sharing used hypodermic needles.

  • Gia Carangi: Life and death, energy and peace. If I stop today it was still worth it. Even the terrible mistakes that I made and would have unmade if I could. The pains that have burned me and scarred my soul, it was worth it, for having been allowed to walk where I've walked, which was to hell on earth, heaven on earth, back again, into, under, far in between, through it, in it, and above.

Angelina Jolie as "Gia"
Angelina Jolie as "Gia"
The real Gia Marie Carangi
The real Gia Marie Carangi


Another true story, based on the life of Aileen Wuornos (played by Charlize Theron), a serial killer from Daytona Beach, Florida. Before succumbing to her fate as a murderess, she meets Selby (Christina Ricci), a lonely lesbian who has no friends, which works out perfectly for Wuornos, a lonely prostitute who has no friends. Wuornos promises Selby the world, but when she kills a john after getting raped she can't seem to stop murdering and then robbing her clients. Earned it's Tearjerker Status Because: Selby ends up selling her out and phone tapping her for the police, and Aileen ends up being executed.

  • Selby: I just wanna live, Lee. I just want a normal happy life. I don't know why you did this.

  • Aileen: Because I love you. Because I love you and I never wanted to lose you and that's all. I love you from my heart, my soul, my mind. And I never let you down. All right? Because it was me. It was only me. And I'll tell them that, ok. It's over for me now. And I'm never gonna see you again.

Charlize Theron underwent a monster transformation to prepare for the role of Aileen Wuornos
Charlize Theron underwent a monster transformation to prepare for the role of Aileen Wuornos


Rising young star Erin Kelly plays the role of the title character, "Annabelle", a senator's daughter and misunderstood, rebellious 17-year old who is sensitive yet strong. When it comes to seducing her English teacher, Simone (Diane Gaidry), Annabelle's self-confidence and stamina are unparalleled. But in their private Catholic boarding school setting, a lesbian love affair, especially between a teacher and a student, is strictly forbidden. This doesn't stop Annabelle from pursuing the object of her affection, however, and after a frustratingly long amount of time, Simone can no longer resist her attraction. Earned it's Tearjerker Status Because: Just when teacher and student consummate their long-awaited love affair, they are found out...and that's where the movie ends.

  • Simone: (as they're about to kiss) I can't do this...
  • Annabelle: We're not doing anything wrong.


This movie is twisted the way "Memento" and "Eternal Sunshine of the Spotless Mind" are -- you'll probably have to watch it several times before you fully understand it, and even then you'll search online for different interpretations of the plot. "Mulholland Drive" is a sexy, sultry, surreal and slightly psychotic story about a woman named Rita (Laura Elena Herring) who suffers from amnesia after a car crash and ends up wandering into the home of Betty (Naomi Watts). The two women try to uncover Rita's true identity as they navigate their way through a web of mystery that involves a nightclub called "Silencio", a small blue box, and a cowboy. Earns it's Tearjerker Status Because: It's all just an illusion.

  • Betty Elms: [after kissing Rita] Have you ever done this before?

  • Rita: I don't know. Have you?

  • Betty Elms: I want to with you.


Want to see these movies for yourself? DON'T YOU DARE BUY THEM RETAIL. Why spend $19.99 on one movie when you can get all five shown here for the same price? I swear by, an eBay affiliate that's better than eBay and Amazon combined. Find great deals on videos and DVDs at Just click this link and type the name of the movie into the search box. You can get "High Art" for $1.75 and Monster for a whopping $0.75. I kid you not.






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    • profile image

      amin bvbcvt 6 years ago

      My personal favorite movie based on a true story was Defiance.

      I voted for Enemy at the Gates, because I'm always very partial to snipers and I did like it quite a bit. But I didn't like the setting and the scenes. They weren't dirty or chaotic enough, a little bit too much of a fake feel. And I hate sex scenes.

      Catch Me if You Can was very good, and Black Hawk Down was nice. One reason I didn't like Black Hawk Down was that it didn't portray or explain everything as fully as it could. It left out quite a number of pieces and inserted a few others.

      Simply because I'm not a sucker for mobster movies, I'm not really aware of many of your picks.

      Good review though.

      @ d,

      Braveheart horribly destroyed the real life events. The fighting in it was good, but almost nothing was done right.

    • profile image

      Dean 7 years ago

      Marta Baletbó-Coll made a film called "Sévigné". She not only wrote it but she directed and starred in it, if you can imagine!

      Done originally in Catalán which is, I believe, a dialect of Spanish, you can also see it with an english language track or with english subtitles. Either way, the love story told is so full of real chemistry and passion it grips you and you don't even want to blink while watching because you don't want to miss a moment of it.

      I first saw it on youtube and coincidentally started up a conversation with Marta herself there and she was generous enough to send me a copy of it and two other of her films on dvd free of charge. I HIGHLY recommend seeing this film. It will change the way you think about romance and love in the movies, for the better.


      Dean Andreoli

      Portland, Maine

    • Cheeky Girl profile image

      Cassandra Mantis 7 years ago from UK and Nerujenia

      I have most of these. Now I will soon have ALL of these! : )

    • profile image

      Stephanie 8 years ago

      Wow!! Nice collection of Videos.You can also get the DVD of I can't think straight from Enlightenment is the link:

    • Alana Obe profile image

      Alana Obe 8 years ago from My mind...

      Great movie picks! I adore High Art, it's in my top 5 all time movies, although tragic, along with Monster, they deplect such great love affairs between women. Great Hub!

    • petexanh profile image

      Peter 9 years ago

      I'm going to check out a few of these myself. I loved Monster. Don't know if I would call it a great date movie though. Didn't come out feeling warm and fuzzy and wanting to be in a relationship ;).

    • Sadie_H profile image

      Sadie_H 9 years ago

      I love this kind of movie--I saw "High Art" on Netflix and was curious about it. Now I'm going to add it to my list! Thanks!

    • profile image

      samer 9 years ago


    • lavenderstreak profile image

      lavenderstreak 9 years ago from Seattle

      How about Desert Hearts? I love the movie. It's based on Jane Rule's Desert of the Heart, a book I read in the 70s. I think the movie came out in the mid to late 80s.

    • puter_dr profile image

      puter_dr 10 years ago from Midwest USA

      Good picks. I have seen Gia and Monster. Have to get the others on order from Netflix.

      If you want movie recommendations, you may have seen there already, but my lesbian friends love Rent, Hedwig and the angry inch, Rocky Horror Picture Show, Frida, Bound, Boys Don't Cry, Better than Chocolate, Lost and Delirious

    • becauseilive profile image

      becauseilive 10 years ago from N.J.

      If I HAD to choose, I'd say move "High Art" right to the top of your queue -- followed by "Gia" and then "Loving Annabelle". I'm so glad someone enjoyed this! And now I'm interested to know what other movies you have in your Netflix queue, cause I am in desperate need of new recommendations.

    • livelonger profile image

      Jason Menayan 10 years ago from San Francisco

      I LOVED Mulholland Drive and Monster. Will add the others to my Netflix queue...