I should say first of all that, actually, I probably don’t qualify as a “sad person”, not anymore. In fact, at 36, I’m the happiest I’ve ever been. I’ve been married to my #1 person for almost nine years now, and we have a really fun, healthy, almost suspiciously good relationship, and four kids together. And no drama to speak of. This is the first healthy relationship that I’ve ever had, and the only one that’s lasted longer than six months! It’s great.

However, as a melancholic and an intuitive introverted personality type and someone with AVPD, I’m just kind of a sad person by nature. Maybe that’s why I love tragic love stories so much — way more than the kind with a “happily ever after.” A love story is just so much more delicious, more tantalizing, more moving, when it’s unfulfilled somehow — when there’s something to long for. When they can’t be together, when circumstances (tragic or otherwise) keep them apart.

My husband thinks it’s funny how, when we’re watching a movie or show with a romantic plot thread, I’ll always be like: “wow, those characters have such chemistry! I hope one of them dies. 😍”

Why are we like this? Obviously, I don’t actually like it in real life, if someone I know loses a partner or a relationship ends tragically. I think in fiction there’s something cathartic about it — I mean, there’s a reason humans seek out sad stories, scary stories, dark and grisly stories. It’s a safe way of experiencing intense emotion.

And we all know the forbidden fruit effect. Something is all the more alluring when you can’t have it. It’s similar to the way I feel about dessert. The longing for a thing is often more satisfying than the thing itself. So that’s probably got something to do with it as well.

It’s in this spirit that I’ve compiled the following list of my top ten favorite sad love songs for sad people. I’m including some suggestions for places where you can listen to these while crying, to really maximize the effect.

16. “We Both Go Down Together” by The Decemberists. But is it tragic because they’re in love and willing to die together, or is the singer actually abusive and insane and the girl is his victim? I know it’s been hotly contested. I prefer the first interpretation. Suggested crying location: the Cliffs of Dover, obviously, but if you don’t have the Cliffs of Dover at home, your nearest precipice will do.

15. “Back Of My Mind” by Two Feet. This one’s more about longing than tragedy I guess, but it’s still definitely a sad song for sad people. Suggested cry spot: in a dimly-lit bar late at night.

14. “The Highwayman” adapted and performed by Loreena McKennitt. We all know the poem by Alfred Noyes. It’s one of my favs. The quintessential tragic romance, basically. Suggested cry spot: outside, at night, when the weather is misty and no warmer than 60°F.

13. “I Will Follow You into the Dark” by Death Cab for Cutie. Remember this one? It’s too sad even for me. Suggested cry spot: public transport.

12. “My Last Breath” by Evanescence. No one has ever made death sound as sexy as Amy Lee makes it sound in this song. This whole album rocks and I will die on this hill. Suggested cry spot: at your desk (you are wearing headphones).

11. “Existentialism on Prom Night” by Straylight Run. Remember this one, too? I actually bought the CD because of how much I liked this song, but the rest were not as good. Still just as freaking sad as it was back in the days of buying CDs. Suggested cry spot: on your bed, supine, looking up at the ceiling. Your bed should be unmade and your room messy.

10. “9 Crimes” by Damien Rice. This song is about infidelity, which is, in all seriousness now, extremely sad — but, I’m obsessed with it. Suggested cry location: in a busy restaurant at lunchtime, or alternatively: standing by the side of the road (in broad daylight).

9. “High Flying Seagull” by Dougie MacLean. Just a pretty little love song about a sad guy and his girl. Suggested cry spot: the beach (when it’s overcast). If you can’t get to the rocky coast of Scotland, your nearest beach will suffice.

8. “Lay Your Head Down” by Peter Bradley Adams. This one haunts me. It’s just a brutal work of art. Suggested cry spot: the floor.

7. “Thief” by Our Lady Peace. I think I remember reading somewhere that this was written about a friend, not a partner, but it’s still a love song and could very well be about anyone you love who’s suffering and there’s nothing you can do to help them. Suggested cry spot: waiting room.

6. “Sahara Love” by Above & Beyond feat. Zoë Johnston (Seven Lions Remix). Tfw you have so much more to say to someone but you can’t. You MUST cry to this in the car, at night, driving fast, like maybe over a bridge, with the stars and/or city lights streaming past you making you feel like you’re in outer space.

5. “Where Are You” by Déanta. An anthem of unrequited love. When I was a junior in high school, the lines “I have built for you a tower of love and admiration/ I see you so high, I cannot reach myself” hit me like a ton of bricks. Suggested cry spot: gazing out a window toward the horizon. There should be trees.

4. “Wake Up, Open The Door And Escape To The Sea” by blaqkaudio. Oof. The feels hit so hard that I can excuse the absent Oxford comma. Suggested cry spot: in the snow, but it’s not actively snowing, it’s like yesterday’s snow or the day before.

3. “Endlessly, She Said” by AFI. Yup, Davey again. His lyrics are my favorite, because they’re so full of metaphor and poetic allusion that it becomes very personal, subject to your own interpretation. The desperation and loneliness in this song, it gets me every time. Suggested crying locale: on the roof of a parking garage at night.

2. “Eclipsed” by Evans Blue. This song was introduced to me by a fellow Sad Girl in ca. 2006-07 (hope she’s doing okay now). I’m still not sure exactly what it’s supposed to be about, but I know what it’s about in my heart. Suggested cry spot: in a burning building.

And finally, what is quite possibly the most heartbreaking love song ever:

1. “Between the Bars” by Elliott Smith. This song! Whether you’ve never heard it before, or you’ve heard it a million times: brace yourself. As a teenager, I always assumed this was a love song about a person, but now, I hear it as a song about alcoholism (like from the pov of the addiction, singing to the addict). Which is still a love song — I mean, that’s the most intense and toxic love relationship that there is. But, you know what, it could also be about a person; these lyrics are so brilliant. Crying location: wherever you happen to be when you hit play, but ideally somewhere deserted, in the very early morning, while the rest of the world is asleep.

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Let me know if you try crying to any of these in any of the suggested locations. Hope you enjoy. Happy Valentine’s Day.