Sarah Handyside’s Heartbreak Playlist

This post was written by Sarah Handyside, author of Instructions for Heartbreak. 

Following my last big breakup I quite literally googled ‘songs to cheer myself up’. It was a half-unhinged, half-human response to a barrage of emotion I had no idea what to do with. This search for a neatly packaged solution is nonsense, of course – but the right music will still go a long way to helping heal your broken heart – as the characters in my novel, Instructions for Heartbreak know…All Too Well? (Sorry).

But having reflected on it more, I actually think there are two kinds of heartbreak song. Yes, you need the kind that will whiplash you out of your misery – but you also need the kind that will lean into it. The kind that you’ll dance your brains out to, waving a treble vodka tonic, but also the kind that you’ll listen to alone in your bedroom, burning the mementos they left you.

Here’s my pick of each – and for more excellent options, do check out what my Heartbreak Seven guests have to say on the matter.

Shout Out To My Ex by Little Mix

Like the Spice Girls before them, Little Mix are truly a girls’ girl group. You know they’re having fun up there. You know that a night out with them would end up with tequila slammers and dancing on tables. You know they’ve got your back. Shout Out To My Ex is this vibe personified. Grab your girls, get on the dancefloor and scream out lines like ‘ain’t sure I loved you anyway’ as you skate around your own post-breakup mind games. Do I really believe that, or am I just trying to believe that?

Without You by Harry Nilsson

Yes, it risks veering into cliché territory. But you need at least one bona fide power ballad, one indulgence of every piece of rock-bottom emotion, and if it’s not going to be All By Myself (the Jamie O’Neal version from the opening of Bridget Jones, obviously) then it has to be – has to be! – this. And – with thanks to an adored friend for pointing this out – adding to its power is the fact that the verse mimics the melody of the Rachmaninov concerto used in Brief Encounter, stirring further subconscious agonies of lost loves and missed connections.

You Oughta Know by Alanis Morissette

An angry girl anthem, made for snarling in your car as you drive away from the burning wreckage of your relationship – which they messed up, obviously.

I Can Do It With A Broken Heart by Taylor Swift

I mean, the doyenne of heartbroken millennial women could appear in this list fifty times. Honourable mentions to So Long, London (that church bells-esque intro! I’m pissed off you let me give you all that youth for free!), All Too Well (the scarf! maybe this thing was a masterpiece ’til you tore it all up!) and My Boy Only Breaks His Favourite Toys (that metaphor truly pushed to its limits! I’ll tell you that he runs because he loves me!) But I Can Do It With A Broken Heart is for both wallowing in your misery and reminding yourself of your own strength. A banger.

If You See Her, Say Hello by Bob Dylan

Blood On The Tracks is the perfect breakup album, covering the full gamut from introspective misery to no-looking-back fury. (Someone on X claimed that the record made them want to get divorced aged thirteen). If you’re in an angry place, stick at Idiot Wind – but if you’re feeling tearful, this quiet, tender song is a perfect reflection on the dissonance that someone once so close is now a (partial) stranger.

With, of course, a hint of bitterness – this is Bob after all.

Like A Friend by Pulp                                                                                 

A track that straddles the two types of heartbreak song, and one that’s perhaps more strictly about unrequited love than the end of a relationship – though no less devastating for that. That singalong second half was made for waving a beer around whilst shrieking ‘you are the drink I never should have drunk…’

Dancing On My Own by Robyn

A happy-sad masterpiece. I really, really hope you’re not actually in the corner watching him kiss her – but if you are – or if you’re just picturing it – than this is the medicine you need.

Is That All There Is? by Peggy Lee

Perhaps a sad-happy masterpiece? When your metaphorical house has caught fire, when your life is a metaphorical circus, this song is a reminder of all the catastrophes that have gone before and all the calamities you have walked through. ‘We were so very much in love, then one day he went away and I thought I’d die, but I didn’t.’ It’s simple, it’s perfect. All we can really do is keep dancing, break out the booze and have a ball.

Both Sides Now by Joni Mitchell (2000 version)

Another that comes dangerously close to cliché, now that we’re all picturing lovely Emma Thompson in her tasteful slip, weeping over horrid Alan Rickman. But Joni Mitchell’s melody is as beautiful as her word play, and this version, with its lush, swelling orchestra, will make your heart explode.

I Don’t Want To Get Over You by The Magnetic Fields

Just about any track from 69 Love Songs belongs here but this, like the very best, is simultaneously acerbic and irreverent, heartbreaking and hilarious.

I Will Survive by Gloria Gaynor

No explanation needed.

Martha by Tom Waits

Because in it is the hope that while time can heal all wounds, it doesn’t diminish our desire and need for love, and it hints at the possibility that reconciliation and rekindling may be possible after half a century apart. And really, isn’t that the very hope that all romantics cling to?

Sarah Handyside’s Instructions for Heartbreak is available to buy now.