Looking Back is a Bad Dating Strategy

Welcome to Girlfriend Material, your weekly rundown of realistic, impactful actions you can take to level up…alongside random rumblings from the back of my brain. You can upgrade to a paid subscription here for exclusive style resources. Here’s a template to get your wife or girlfriend’s sign-off.

I think she finally did it.

Taylor Swift may have really, truly broken my addiction to dwelling on the past.

Last week, the newly-married singer released an “encore” to Life Of A Showgirl. Four extra songs extending the shelf life of her most recent album.

They were …fine.

Nothing’s going in the canon (a Mount Rushmore that includes “Blank Space” and “All Too Well [10 Minute Version]”). One song, though, will stick with me.

On “Cleveland!” (yes, with a “!”), she sings about her and new husband Travis Kelce’s love story.

Except it’s less an ode to the two of them, and more a retort to random internet haters who’ve questioned her dating choices and ::checks notes:: dance moves.

It reminded me of—and stay with me here—Ashlee Simpson’s alleged altercation with Pete Wentz’s old girlfriend in the early aughts:

screenshot of a Today.com synopsis that reads: Ashlee Simpson yelled at Pete Wentz's ex-girlfriend, actress Michelle Trachtenberg, at an LA party in June 2009. At the event, a heavily drinking Simpson confronted Trachtenberg and screamed in her face: "I hope you know, the whole time you were dating Pete, I was f**king him." At the time of the incident, Simpson and Wentz were already married and had a young son together, having wed in May 2008.

(Why these anecdotes lodge themselves in my brain but I can’t remember where I put my passport..who knows?)

Like, okay? Go off, I guess, girl.

Listening to “Cleveland!,” I kept thinking: Why are you still looking backwards, Taylor Swift?! Do you not know you’re Taylor Swift?! You have a very nice life! Go enjoy it!

It’s easy to get addicted to licking our wounds.

Was it the relationship you stayed in too long? The career move you wish you’d made sooner? The fact that someone else got the thing you thought was supposed to be yours by now?

And look, the diagnosis is useful. Hard experiences are worth learning from.

But there’s a point where trying to understand the past becomes a way of staying stuck in it.

I say this as someone who has seriously considered hiring an Etsy witch to excise the bad juju from 2015 when an ambitious intern spammed Reddit with SG links and got us banned from the platform.

Because, in my brain, that’s why we’re still not competing with the GQ’s and Esquire’s of the world.

And maybe it's true?! Maybe it isn't. At this point, it doesn't really matter.

Style Girlfriend is here. I'm here. So what are we going to do next?

You can spend a lot of energy ruminating on the past, or you can ask:

Okay. What do I want now, and how do I go get it?

That doesn't mean pretending the past didn't happen. It means refusing to let it control your present.

This feels especially relevant to dating.

Whether you're 24 and trying to figure out what the hell you're doing, 42 and wondering if you're behind, or 58 and fresh off a divorce, it's very easy to get caught up in a “Woe is me” story of what hasn't worked.

We'd rather help you think about what's next.

It’s why our team put together The Style Girlfriend Dating Guides, created in collaboration with Hims: four actionable guides for dating in your 20s, 30s, 40s, and 50+.

Each one is built around the particular questions, challenges, and opportunities that come with dating at that stage of life—from navigating the apps to feeling confident in your appearance.

Because wherever you are in your dating journey, you don't need to keep looking over your shoulder at where you've been.

You can turn around. Face forward. And go see what's next.