Dear Anna,

I’ve been broken up with my ex for almost four months now. I did everything the experts recommend—blocked him on social media, deleted his number, and even asked mutual friends not to mention him. I was doing well until I realized I could still see his Spotify playlists even though I blocked him. Now I find myself checking them obsessively. Every new song he adds feels like it might contain a message for me—whether he misses me, is angry with me, is moving on, etc.

I know this behavior isn’t a great use of my time, but I can’t seem to stop. I’ve memorized his listening patterns and check for updates multiple times daily. Sometimes I even create my own playlists with songs I hope he’ll notice, though I have no idea if he even looks at my account anymore. How do I break this last digital connection when it feels like my only remaining window into his life? Is there any chance he really is communicating through these playlists, or am I just torturing myself?—Discovering Joy Separate from A Dance Soundtrack

Dear DJSADS,

The heart is amazing at finding loopholes, isn’t it? You barricade all the windows to your loneliness and pain, only for that fucker to sneak in through the dog door.  

I get it. I too have tediously analyzed an ex’s music playlists, searching for myself, searching for clues about how she was faring in my absence, but mostly to reassure myself that she was hurting as much as I was. We do this not because we’re masochists but because the human mind craves patterns and meaning, especially when our hearts are still processing loss. And the human heart is the greatest enabler there is.

The digital age has, unfortunately, given us so many strange new forms of lingering, where we can be both completely separated yet secretly connected, secretly watching.

There’s also something painfully intimate yet safe-seeming about watching someone’s music choices unfold from a distance. It’s easy to convince yourself that what you’re doing is harmless. It’s not like you’re texting them or watching their reels on a loop.

But—

You knew there was a but, right?

Think about what checking his playlists actually gives you: momentary connection followed by hours of ruminating, uncertainty, and pain. It’s like pressing on a bruise to remember what caused it.

Because when you do listen to his music, you’re reopening the wound just a tiny bit. You’re prolonging the healing that you need to move on.

Here’s the difficult truth: You’re standing at the edge of an ocean, convincing yourself you can decode the movements of a single wave. But these playlists likely aren’t cryptic communications—they’re simply the soundtrack to his continuing life, one that’s now separate from yours.

And even if he is sending messages to you, ask yourself why you need to receive them? What good could come from it? Messages sent through such an indirect channel are rarely clear or constructive. They exist in a murky realm of plausible deniability—designed to affect you without requiring any actual vulnerability or accountability from him.

Consider what you’re truly seeking in these playlists. Is it closure? Confirmation that he’s suffering too? Evidence that you still matter? These are natural desires after a relationship ends, but they can’t be satisfied by analyzing song lyrics. All they do is keep you tethered to a relationship that no longer exists except in memory and speculation.

The most painful realization might be this: Whether he’s thinking of you or not, whether those songs are about you or completely unrelated, the outcome remains the same. You’re still broken up. You still need to heal. And healing, especially in the early days, requires closing even the smallest windows that let in the draft of what-ifs and maybe-stills.

Your attention is precious—it’s the currency of your life. Every minute spent decoding his musical choices is a minute not invested in your own renewal. It’s time diverted from discovering what your life sounds like without the background noise of this relationship.

Remember that true messages worth receiving come directly, honestly, and with clear intentions. They don’t require endless interpretation or leave you guessing. They don’t maintain ambiguity or keep you suspended in uncertainty.

You deserve communication that serves your healing, not speculation that prolongs your pain. And most importantly, you deserve to be the composer of your own life’s soundtrack—one that plays forward, not on endless repeat.

You’ve done the difficult work of blocking contact elsewhere—actions that took courage and self-respect. This final digital tether is keeping you suspended between moving forward and looking back.

Your healing doesn’t lie in deciphering his music choices but in reclaiming your own soundtrack. Music has real power—it can transport us through time and emotion. Right now, you’re using that power to stay tethered to the past instead of scoring your future.

Try this: Create a playlist that has nothing to do with him. Fill it with songs that speak to where you want to be, not where you’ve been. When the urge to check his account surfaces, play your forward-looking music instead. (Or add new songs to it. Or share it with someone else who might need a boost.)

Create a new account for yourself if you need more distance. (You can always come back to the old one when you’re ready.) The temporary pain of losing this connection will be nothing compared to the freedom waiting on the other side.

A few months from now, you could still be analyzing his playlists for hidden meanings—or you could be living fully in your present, with music that celebrates where you’re going and who you are.

You deserve to be the protagonist of your own story, not a spectator to his. The moment you cut this final cord is the moment your own music can finally play without interference.

Your future is waiting. It has its own soundtrack, and it sounds like wholeness. Listen close.

Anna Pulley is a syndicated Tribune Content Agency columnist answering reader questions about love, sex and dating. Send your questions via email (anonymity guaranteed) to redeyedating@gmail.com, sign up for her infrequent (yet amazing) newsletter, or check out her books!

This column originally appeared on The Chicago Tribune.