Valentine’s Day Mix Tape 101: 43 Love Songs, 49 Anti-Love Songs & Some Videos!

In the process of creating the Valentine’s mix tape, a few Autostraddlers confessed that this year their Valentine’s Day will probs be less about love song dedications and more about sitting out the front of their ex-lovers house, seranading them with the Kaiser Chief’s “Every Day I Love You Less And Less” via their sub woofer. Which is why we’ve also created a special B Side of anti-love songs for those of you who have a different sort of mix tape in mind.

Valentine’s Day Mix Tape B Sides: The Anti-Love Tracks

Lucinda Williams – “Ventura”
Best with a broken heart & too many empty bottles of whiskey.

PJ Harvey – “Long Snake Moan”
Everything is fucked, let’s have angry sex.

Ryan Adams – “Come Pick Me Up”
Fuck, this breakup just got messy.

Neko Case – “Twist the Knife”
I’m spurned but hell, I’m honest.

Neko Case – “This Tornado Loves You”
It’s Understandable You Filed That Restraining Order.

A Perfect Circle – “3 Libras”
A girl gave me this song on a mix tape once and it did not feel good. It’s a kick in the gut.

Jeff Buckley – “The Last Goodbye”
Just flat out heart-wrenching.

Jay-Z – “99 Problems”
“If you’re having girl problems I feel bad for you son, but I got 99 problems and a bitch ain’t one.” Just shake it off.

Hunter Valentine – “Jimmy Dean”
“I don’t want to make love, I want to fuck with abandon. I don’t want no sweet valentine, I want a shot of jack to forget this time.” The way this girl sings is so hot that you’ll forget about whoever you’re moping over.

Bright Eyes – “It’s Cool, We Can Still Be Friends”
This song should come with a warning: May make you want to fucking kill yourself.

Chris Pureka – “Momentary Thief “
“I’ll tell you what/I’ll save you the trouble of running away/yeah I’m already at the door/and I stole this moment for me.”

Fiona Apple – “Paper Bag” & “Get Gone” but really all of “When the Pawn.”
“‘You got your game, made your shot, and you got away / With a lot, but I’m not turned-on/ So put away that meat you’re selling /Cuz I do know what’s good for me-
/ And I’ve done what I could for you/ But you’re not benefiting… it’s time the truth is out that he don’t give a shit about me.”

Liz Phair – “Fuck and Run”
This was good to sing in the 90’s when you didn’t want to have feelings. Then in the ’00s maybe you realized that there were feelings in this song, like that she actually wanted a boyfriend to win her over. So then it has many layers, like a cake.

Dar Williams – “As Cool as I Am”
It’s happy but it’s about moving on: “So you’re leaving/you can find out how much better things can get/and if it helps/I’d say I feel a little worse than I did when we met/so when you find someone else/you can try again/it might work next time.”

Hilary Duff – “So Yesterday”
If you sing it over and over and over again it starts to feel true!

Shiny Toy Guns – “Don’t Cry Out
It’s such a simple phrase, I should’ve thought of it myself — “I don’t get you, I can’t forget what you’ve forgotten” — but I didn’t, they did, and they sang it; and it was wholly, completely, entirely literally true.

Ani DiFranco – Dilate
“I just want you to live up to / the image of you I create / I see you and I’m so unsatisfied / I see you and I dilate.”

Rilo Kiley – “A Man / Me / Then Jim”
It’s partially about suicide, which is a lot. But it’s also beautiful. And one time Jenny Lewis looked right at me while she sang the best part, and I almost passed out in the front row.

The Mountain Goats – Woke Up New
It’s about waking up the first day after a breakup. Surprisingly hopeful, given the subject.

The Postal Service – “Nothing Better”

Jimmy Eat World – “Hear You Me”
To help you get over someone you lost.

Thao + The Get Down Stay Down – “Easy”
Sad people dance, too!

Jessica Lea Mayfield – “We’ve Never Lied”
Stinging and honest. I’m sad just thinking about it. Damn.

Third Eye Blind – “How’s It Gonna Be”
“How’s it gonna be / when you don’t know me anymore.” #wallow

No Doubt – “Ex Girlfriend” or “Don’t Speak”
Pick one. Are you indignant and sassy? “Ex Girlfriend” is for you. Are you a little sad for real? Feel it in your bones? “Don’t Speak” is your jam.

Rolling Stones – “Angie”
Baby let’s just cry. Get it all out. They can’t say we never tried.

The Muffs – “Red Eyed Troll”
This was my favorite high school breakup / angsty song! Lots of screaming.

Beyoncé – “Irreplaceable”
You don’t wanna treat me right? YOUR LOSS, SUCKA!

Atmosphere – “Fuck You Lucy”
I like songs that say ‘fuck’ a lot when I’m bitter. Sometimes you just wanna shout “FUCK YOU” to love.

Mariah Carey – “Shake It Off”
Bad break-up? You’re better off anyway. Mariah Carey always makes things better for me.

The Ataris – “The Last Song I Will Ever Write About A Girl”
While my adolescent skater punk days are (mostly) behind me, shouting “GIRLS ARE FUCKING EVIL” is still necessary sometimes.

The Mountain Goats – “No Children”
Vehemently hating your spouse has never sounded so upbeat and catchy! Seriously, the lyrics to this are genius.

The Clash – “Train In Vain (Stand By Me”)
Shake it out and dance up a frenzy to this classic by The Clash. A catchy and upbeat chorus is juxtaposed with lyrics of loneliness and abandonment.

The Decemberists- “The Engine Driver”
For the poet in all of us, Colin Meloy offers this tune featuring some of his most beautifully crafted lyrics. If you’re trying to get over her and can’t, discover emotional solidarity here: “And I’ve written pages upon pages / Trying to rid you from my bones.”

Blessid Union of Souls – “Light In Your Eyes
I heard this song for the first time since, like, 1999 a few weeks ago and was reminded about everything that was great about the last ’90s. Oh yeah, and it’s about breaking up and stuff.

Rihanna – “Hard”
Speaking from experience, the best time to listen to this song is when you’re angry and dressed up in heels [or kicks or however you roll] because then you can stomp around and think thoughts like “fuck the man! and also you!” when you see the person you’re mad at. It is very empowering.

Ingrid Michaelson – “Sort Of”
Guys, “my love’s too big for you” is such a not fun feeling but Ingrid’s so cute about it. No sane person would ever break her heart, you know?

Belle and Sebastian – “I Don’t Love Anyone”
Gram Parsons and Emmylou Harris – “Love Hurts”
Bob Dylan – “It Ain’t Me, Babe”
Band of Horses – “No One’s Gonna Love You”
Elliott Smith – “Somebody That I Used To Know”

The Cinematic Orchestra – “To Build A Home”
Hands down one of the most beautifully orchestrated, heart-wrenching, excruciatingly loving, beautifully sang song that I’ve ever heard. Listen to it. It’s close to perfect.

Glen Hansard & Marketa Irglova – “When Your Mind’s Made Up”
Everyone has felt abandoned by the one they love. This is the perfect song to drive and cry about it to.

Rachael Yamagata – “Even So”
Written by a woman who broke her own heart by cheating on the only man she loved and who loved her in return. Get ready to feel.

Tegan and Sara – “Call It Off”
“Call, break my own heart”…

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Founding member. Former writer. Still loves Autostraddle with her whole heart.

Crystal has written 320 articles for us.


  1. Yeah, I’m going to be listening to side B this valentines.
    Heres my two cense:

    Alanis Morissette- You ‘Oughta Know
    Ani DiFranco- Untouchable Face (Fuck You)
    Florence + The Machine- Kiss With A Fist
    Bright Eyes- A Perfect Sonnet
    Cat Power- Aretha, Sing One For Me
    Ingrid Michelson- Breakable

  2. I love this! I am going to listen to every song.

    In love:
    Ashanti- Don;t Let Them
    Mariah Carey- Joyride
    Maxwell- Fortunate
    An Horse- Listen- The prettiest lyrics ever!
    Lenny Williams- Because I love you- The realest song ever sung to a woman
    The Delphonics-Hey Love
    Ojays- We Cry Togther- Which is the most beautiful, saddest, realest song that will take any situation from vertical to horizontal by the first chorus.

    Breaking up:
    Anthony Hamilton- I’m a Mess
    John Mayer- Slow Dancing in a Burning Room
    Laryn Hill- Ex Factor
    Fiest-Let It Die

  3. I’m so happy about all the Mountain Goats love here! Also, I am seriously considering having my Valentine’s Day just be listening to the Black Album (or maybe just 99 problems) on repeat. LADIES IS PIMPS TOO

  4. Awesome list… I think the Dar Williams lyrics are “and so I’m leaving,” not “and so you’re leaving.” The song’s about a guy who makes lots of backhanded comments to push at her insecurities, but she won’t take it!

    • I actually wrote that in from memory, I didn’t even look up the lyrics. I imagine i’ve been yelling the words over the actual recording so loudly for so long that I don’t even hear what she’s singing anymore!

  5. I thought of another break-up song that yells ‘FUCK’ – Rootless Tree by Damien Rice. “FUCK YOU AND ALL WE’VE BEEN THROUGH!”

    I adore the anti-love songs Crystal picked, but 3 Libras and Last Goodbye make me all sad, whereas I prefer fervid resentment.

    • i was listening to this today only i was thinking “eff you snow, i don’t like walking home through you.” only i do cause i’m still in love with snow kinda like how you’re still in love with people even when you hate them. HI i’m drunk.

  6. I’m going to make a ‘Love’ song mix using Isa and Emily’s songs and an ‘Anti-Love’ mix using Riese and Laneia’s. On Sunday you’ll find me listening to my own ‘Yay, girls rock & don’t even NEED valentines so suck on that, society! mix.

    • ah yes, that masterpiece of allegorical artistic triumph. really encapsulated all my feelings about heart, love, endurance, and how things go on despite inclement weather or illiteracy or shattered bloody hymens. how could i forget. bless you, paper. bless you.

      • See? And everyone thought you were one of the haters. Now we see that, deep down, T-Swizzle’s words just cut you too deeply. Your own experiences were too similar to hers. And as you imagined yourself back in high school, saw yourself throwing pebbles at Romeo–oh wait. I’m fucking this up, aren’t I?

    • Oh, and just about everything by Lamb, but especially Gabriel, Gorecki, Heaven, One, God Bless, Cotton Wool and Sweet.

    • i like this! but if we made a “i’m trying to get you to break up with me” mix, i’d put “your body is a wonderland” on it.

  7. no Nick Cave? IMO he wrote some of the best love songs ever.

    some of mine:
    Nick Cave – Straight to you, Are you the one that I’ve been waiting for, Lie down here and be my girl, There she goes,my beautiful world
    The Walkabouts – Till I reach you, All for this
    Uh Huh Her – Wait another day
    The Cure – Lovesong, Just like heaven
    Juliette & the Licks – By the heat of your light
    Neko Case – This tornado loves you
    Neil Young – Pardon my heart
    PJ Harvey – You said something
    The Posies – Anything and everything
    R.E.M. – At my most beautiful
    Placebo – I’ll be yours
    Mazzy Star – Fade into you

    as for anti-love/break up songs, anything from Fleetwood Mac’s Rumours, Marianne Faithfull’s Why’d ya do it, about half of the stuff Morrissey wrote, whether solo or with The Smiths and R.E.M.’s The one I love

    • MAZZY STAR!! i loved them so. and then my friend lauren stole my cd and said she didn’t, in like 1995. so sad.

    • God that is my favorite REM Song!!! I love how it out-dates itself: “I read bad poetry into your machine” hahaha who has an answering machine anymore? :)

      I’d like to second so many songs from above for the A side like Queen and Lauryn Hill. I think I’m going to take it old school and add Ella and Louis Armstrong’s duet “Cheek to Cheek” so good. There are so many more I could add, BUT it’d end up being several pages so I’m going to not do that haha.

      For B Side I think Tracy Chapman’s “Baby Can I Hold You Tonight”– you think it’s a romantic song but it’s just really not.

  8. I totally agree with:

    Guns N Rose – Patience
    Yeah Yeah Yeahs – Maps
    Bright Eyes – First Day of my Life
    Iron & Wine – Naked as We Came
    Glen Hansard & Marketa Irglova – Falling Slowly

    Ryan Adams – Come Pick Me Up
    Third Eye Blind – How’s It Gonna Be
    Beyonce – Irreplaceable
    The Cinematic Orchestra – To Build A Home

    And I’ll add:

    Paramore – The Only Exception
    Adele – Make You Feel My Love
    Death Cab – Marching Bands of Manhattan
    Grizzly Bear – Two Weeks

    Laura Marling – Old Stone
    La Roux – Cover My Eyes
    Bon Iver – Woods
    Paper Route – Second Chances
    Frightened Rabbit – ‘Poke’, ‘Good Arms Vs Bad Arms’ and ‘Floating in the Forth’ – seriously recommend these guys

  9. i love that there are more anti-valentine’s day songs than there are actual love songs.

    anyways i totally agree with “first day of my life” and if i had to add another love song i would pick “lion’s mane” by iron & wine. also, “yellow” by coldplay. i’m surprised no one mentioned that, that one’s like a token love song.

    for anti-love songs i would also pick “deanne the arsonist” by atreyu if you want to get really mad and smash things. “fuck off, like you’re the only one who has ever cried or been broken by love.”

  10. In love:
    Trouble Sleeping – Corinne Bailey Rae
    Crazy for you – Adele
    Breathless – Corinne Bailey Rae
    Lucky – Jason Mraz
    Today-Joshua Radin (he played it for Ellen and Portia at their wedding. you can’t go wrong with that.)

    Breaking up:
    Love is a Losing Game – Amy Winehouse
    That’s It, I Quit, I’m Moving On – Sam Cooke/AMAZING cover by Adele
    Best for Last – Adele (FAVORITE. FAVORITE. FAVORITE)

    yeah…i really like adele and corinne bailey rae, obvs.

    • in photos corinne bailey rae always looks like she’s in love
      in photos amy winehouse always looks like she’s like, “fuck love”
      so that makes sense

  11. music+lists+feelings=win, i might get that made into a t-shirt

    otherwise,for side A, i just came across one of the loveliest songs i’ve heard in a while, “Billie Holiday” by Warpaint.
    for side B, a couple of tracks by etta james and the soundtrack to an almodovar film would do…

  12. So many amazing songs on both lists.

    Ones I’ll add:
    This might become your favorite song and your favorite band. Check them out, because you can still see them in creepy basements and hit your head on the ceiling because you’re jumping around so hard.
    —Algernon Cadwallader-The Stars
    This band is an acquired taste, but this song to me is about the beginning of a relationship that’s amazing and awesome and you’re holding all your excitement in your ribs to keep from exploding with happiness.
    —Coeur de Pirate-Comme des Enfants
    You can pretend this isn’t about a boy, because it’s in French. It basically about having someone still love you when you’re in a relationship with someone else, but you’re in love with the person you’re with and you’re telling them that.
    —Gregory & the Hawk-Boats and Birds
    —Jenny Owen Youngs-Hot in Herre
    Not exactly a love song, but this song should be in EVERY mix you ever make.
    —Postal Service-From Such Great Heights

    —Allison Weiss-The End
    I kind of think of Allison Weiss as a female Conor Oberst, but maybe a little more upbeat.
    —Kickball-Sauvie Island
    —Chris Garneau-Black & Blue
    I love this man. His music is kind of all REALLY, REALLY sad. He’s also openly gay.
    —Regina Spektor-The Flowers
    —She & Him-Please Please Please Let Me Get What I Want
    This is an amazing cover of this song, and I LOVE the Smiths.

  13. I always go the super cheesy / funny route in my mixtape endeavors.

    Backstreet Boys – “The One”
    The Beatles – “Don’t Pass Me By”
    Bon Jovi – “I’ll Be There For You”
    Britney Spears – “(You Drive Me) Crazy”
    Darren Hayes – “I Miss You”
    Death Cab – “I Will Follow You Into The Dark”
    Elvis Presley – “Can’t Help Falling In Love”
    Foo Fighters – “Everlong (Acoustic)”
    Heart – “Alone”
    Ingrid Michaelson – “Die Alone”
    KEF – “Hottie Boombalottie” (Watch the music video of this song. Trust me. )
    OneRepublic – “Come Home”
    The Righteous Brothers – “Unchained Melody”
    Sixpence None The Richer – “Melody Of You”
    Sonny & Cher – “I Got You Babe”
    Spice Girls – “2 Become 1”

    Also, that music video for Melange Lavonne’s Marry Me reminds me of JenRO’s Try It.

  14. soooo many good songs already listed and to list; a few more:

    *Take My Hand – Dido … epic, sweet and lush; will get you laid
    *Touch Me – Rui da Silva … super sexy house tune; will get you laid
    *Cloudbusting – Kate Bush … current gf used this one (successfully) on me; and, I suppose, will get you laid
    *Trouble – Harry Connick, Jr. … simple, sweet and playful
    *Bernadette – Four Tops … golden oldie, shout-it-from-the-rooftops

    *Anything by Alison Krauss, Fleetwood Mac’s “Rumours” (yay ‘Rain’!) or Imogen Heap’s “Hide & Seek” = good for various stages of anti-love wallowing

  15. Bright Eyes is from Omaha, Nebraska, thank you.
    And we are very glad to be known for well.. something.

    Bit of advice: don’t listen to Death Cab for Cutie if you are lonely. They will only make you feel worse inside with their beautiful devil words.

    Also, “make cupcakes” a lot. A lot.

    • you pretty much just said exactly what I was going to say about Bright Eyes. They are pretty much our biggest claim to fame here in Omaha…

  16. I would like to make these lists into giant playlists in my iTunes and then listen to them whenever I am happy/sad. Alex should make album art for them, no?

    Some of my favourite love songs:
    Lover You Should’ve Come Over – Jeff Buckley (although I suppose this could be either a love song or a b side, depending on your mood..)
    June on the West Coast – Bright Eyes
    Can I Stay – Ray Lamontagne

    B Sides:
    Black – Pearl Jam (omg saddest song i will cry every time i hear it)
    Burn – Ray Lamontagne
    Over and Over – Rachael Yamagata
    Now the One You Once Loved is Leaving – Lydia

    I’ll stop cause I could go on for days. But I’d also like to mention to anyone considering trying Laneia’s wonderful cd sleeve template… that I’ve done it many times and it’s fantastic and lovely and so much better than using one of those hot pink slim jewel cases.

  17. So usually when someone asks for suggestions on your top songs/films/cultural manifestation of a certain genre, I will typically gush some freestyle mental effluvia, but this time I thought I’d sit on it a while, until the thoughts had settled and formed a more solid mass. Eugh, I think I just grossed myself out with my own metaphor then.

    Anyway, here are my non-soppy love songs:

    Always on My Mind – Elvis. Just so wonderful in its simplicity.

    Mad About the Boy – Dinah Washington. Yeah, so it’s talking about boys, so what, it’s probably the most elegant and succinct tale of pure, wanton, foolish lust on record.

    Hyperballad – Bjork. Kind of about safety and fragility. Plus the string quartet version is sumptuous.

    Devuelveme la vida – Antonio Orozco and Malu. From what my schoolgirl Spanish is capable of understanding, it’s basically about two people saying sorry that they’ve been twats, but can’t live without each other, so let’s sort this shit out. That’s proper love.

  18. I don’t have time to really comment, but I just wanna say I love that Karmen chose Tegan and Sara’s “Call It Off” for the B side. It’s been on my recent playlist and I’ve been playing it over and over! It’s soooo good!

    And yeah, that’s all I got. Carry on with the love/heartache.

  19. This is off topic but I just want to leave a note. Something on makes my computer screen freeze for about 15 seconds when I initially enter the site. Perhaps the javascript? I’m using firefox, windows vista 64.

    Lauren Hill ft D’angelo – Nothing Even Matters
    Amerie – Nothing Like Loving You
    Drake – Bria’s Interlude/ A Night off
    H-Town – Knockin Boots (Of course)
    Justin Timberlake – Take It From Here
    Mariah Carey – The Roof
    Natasha Ramos – Midnight Hour
    Sade – By Your Side (Neptunes Remix)
    Taio Cruz – She’s Like A Star
    The Dream – Rockin That Shit
    Jagged Edge – In The Morning

    Broken Up/ Single & Jaded
    112 – Love You Like I Did
    Bat For Lashes – What’s A Girl To Do
    D’Angelo – Shit, Damn, Muthfucka
    Duffy – Warwick Avenue
    Maroon 5 – Makes Me Wonder
    Maroon 5 ft Rihanna – If I never See Your Face Again
    Natasha Bedingfield – Single
    Mariah Carey ft Bone Thugs-N-Harmony – Breakdown
    No Doubt – Don’t Speak
    P!nk – Just Like A Pill
    Rihanna – Rehab
    Incubus – 11am

    Just a lil something… ;}

  21. In the despair behind the holiday and a partially induced sugar coma from the cookie recipes, I have used songs from the list and made a mix CD but had to add a few more songs to make it perfect melancholy:

    Joshua Radin-“Just One Of Those Days”
    Frank Sinatra-“Time After Time”
    Eric Clapton-“Tears In Heaven”
    Kings Of Leon-“Mahattan”
    Missy Higgins-“Where I Stood”

    • Good picks. I think Missy’s catalogue could make up a perfect Love / Anti-Love mix tape on its own.

      • Ah, I am so in love with Missy Higgins albums-The Sound of White and On a Clear Night. I’ve never been able to identify with a singer/songwriters lyrics as much as I have with hers,to see her perform live would be an absolute dream come true.

  22. What does it say about me that I know more of the B-side songs? hrmmm..

    More A Sides:
    Serena Ryder – Hiding Place
    Jason Mraz – Butterfly
    Maria Mena – You’re the Only One
    Ingrid Michaelson – You & I

    More B Sides:
    Jill Barber – Measures & Scales
    Pink’s entire Funhouse album

  23. A great anti love and love song all rolled into one is
    Dixie Chicks – Earl
    Maryanne and Wanda <3

  24. I’m still in the midst of Chinese New Year, practically stuck at home with endless family reunions and a cat and my older brother that needs looking after while my mom’s in Germany with my dad. What Valentine’s Day??!!

    Awww… but these songs are so sweet!! I especially like Bright Eyes’ The First Day of My Life. The lyrics are easy to relate to and the tune is geeeennntle just the way I like it. And it brings out all sorts of aspects of love, which made me fall in love with the music vid.

  25. There is a light that never goes out-the smiths
    Heroes-David Bowie
    Wals x 2-Elliot smith
    Tiny girl-Iggy pop

  26. Here I am like 4 months late, but FULL OF SIDE B.

    My initial offerings are:

    There’s a Fine, Fine Line – Avenue Q. “There’s a fine, fine line between love / And a waste of time.” Sad, but good for spitting along to resentfully and/or feeling like an idiot to.

    Still Hurting – Songs From a New World. “Jamie arrived at the end of the line / Jamie’s convinced that the problems are mine /Jamie is probably feeling just fine / And I’m still hurting.” Fuck this is good. Also CELLO PART.

    Why yes, I do feel almost all my feelings with musical theatre. The other ones go through country music. That is because these are the feelingest genres. Thanks for asking.

  27. Now you gotta make a movie list to watch on V-day!!! AND IT MUST INCLUDE IMAGINE ME AND YOU!!! GOD I LUV THAT MOVIE!!!!!

  28. All of you get on Lo Ball- ‘Can’t get me down’
    Yes, its a grungy fem 90s garage band song and it is amazing.

    It was also in legally blonde!

    “It’s over, you told me that you don’t wanna know me. I’m alone now, I know that, you’re never gonna get me down”

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