“You always hurt the one you love, the one you shouldn’t hurt at all.” A collection of films that capture the messiness of love, the heartbreak associate with dissolved relationships, and the realistic concept that sometimes love just isn’t enough from your resident cynic, Michelle Soto.

There will be countless lists of films you watch on Valentine’s Day with your loved one, or films you should watch to fill your heart with love, but this isn’t one of those lists. As a known cynic of love and it’s lifespan, I’m here to provide you with a list of 14 films that will shatter your heart, make you feel empty, and maybe open your world to a possibility of falling in love with the sadness in romance. Some are harder to watch than others, some add comedy to tragedy, but majority, if not all, will give you all of the feels. There are plenty of films that didn’t make the cut, but are equally as tragic, so let me know if you’d like an extended version of this list!

  1. Blue Valentine (2010, Derek Cianfrance)
  2. Eternal Sunshine of the Spotless Mind (2004, Michel Gondry)
  3. Comet (2014, Sam Esmail)
  4. 500 Days of Summer (2009, Marc Webb)
  5. Her (2013, Spike Jonze)
  6. Brief Encounter (1945, David Lean)
  7. Like Crazy (2011, Drake Doremus)
  8. Blue Jay (2016, Alex Lehmann)
  9.  The Umbrellas of Cherbourg (1964, Jacques Demy)
  10. Brokeback Mountain (2005, Ang Lee)
  11. Celeste and Jesse Forever (2012, Lee Toland Kreiger)
  12. 6 Years (2015, Hannah Fridell)
  13. Blue Is the Warmest Color (2013, Abdellatif Kechiche)
  14. Splendor in the Grass (1961, Elia Kazan)