Dear Anna,

I’ve been dating my girlfriend for a little over a year, and for the most part things are great. We’re both pretty sentimental people, but in different ways. I save things — not in a hoarder way, but I’ve kept shoeboxes of old letters, birthday cards and printed photos from past relationships going back to college. I don’t look at them often; maybe once or twice a year I’ll flip through them out of nostalgia, the same way someone might reread an old journal or yearbook. It doesn’t make me miss the people or want anything back. If anything, it reminds me how much I’ve grown and how different my life is now.

My girlfriend recently found one of the boxes while we were reorganizing the closet, and she did not take it well. She asked why I “need” to keep any of this, especially since some of it includes love letters and romantic photos. I told her the truth — that I’m not pining, I’m not comparing, I’m not holding a torch for anyone. It just feels wrong to throw away pieces of my own life. These relationships shaped me, even when they ended badly.

But she insists that keeping this stuff — and especially looking at it — is disrespectful to her. She said it makes her feel like she’s competing with ghosts. I don’t want her to feel insecure, and I’m not trying to hide anything. But I also don’t want to erase my own history to soothe a fear I’m not sure I fully understand. Is it wrong to hold on to memories of past relationships when you’re committed to someone new? Should I get rid of the boxes to make her feel more secure, or should she work through the discomfort on her end? I want to be considerate, but I also don’t want to pretend the life I lived before her never happened. Am I being insensitive, or is she being unfair? — Not Trying to Date My Past

Dear NTDMP,

Let’s start with this: You’re not doing anything strange. Almost everyone keeps artifacts from the life they lived before their current partner — a letter, a playlist, a rock, a yearbook scribble, a photo tucked into a forgotten folder on a hard drive in the garage. Sometimes we don’t even realize we still have these things. When my father died and I was cleaning out his home, I found a birthday card from my orthodontist that I had kept for some reason since I was 12. Why?

Our histories accumulate in drawers and boxes and iClouds the same way our memories accumulate in our bodies. It’s normal to want a record of who you were. It’s normal to revisit it. That doesn’t automatically mean you’re longing for anything (or anyone) you left behind.

But! It’s also normal for your girlfriend to feel a pang when she sees tangible evidence of your old loves. These items aren’t just paper and ink and pixels to her — they’re symbols. Proof that you once felt deeply for other people. Proof that she wasn’t the first, and possibly not the most intense. Many people are fine with their partner’s past in the abstract, but the physical artifacts can feel like emotional clutter encroaching on the present.

So you’re both being human. No villains here.

The real issue is symbolic meaning. For you, these boxes are a museum exhibit. For her, they’re an altar.

That’s why your instinct isn’t to hide them or toss them; you already know they’re inert. But for her, the existence of these objects — and especially the fact that you look at them, regardless of how infrequently — feels alive. Like an open portal to something she can’t see into.

The goal, then, is not to decide whose feelings are “correct,” but whose interpretation needs updating.

Start by explaining in a calm moment (not while either of you is staring at the box): “These things don’t represent desire. They represent memory. They help me remember who I was — not who I want to be with.” You don’t have to use flowery language; just anchor it in emotional reality.

Then ask her two important questions:

“What part of this feels threatening to you?”

Because there are layers here, and she may not even know which one is snagging her heart. It might be comparison — the worry that those letters capture a version of you who felt a kind of intensity she fears she can’t match. It might be disposability — the fear that she could become just another box in your closet someday. Or it might be imagination, the worst culprit of all: When she sees old love notes, she’s not thinking about dusty pages; she’s picturing living, breathing exes with history and inside jokes and moments she was never part of.

Even if you know those relationships are fully dormant, the artifacts are proof they once mattered — and she may not yet know how to hold that truth without shrinking from it.

This is why your tone matters more than your logic.

You’re not trying to win an argument; you’re trying to make room for her feelings without letting them run your life. So when you ask the question, do it gently. Let her talk without immediately reassuring her out of her discomfort. Sometimes people soften the moment they feel allowed to speak the scary thing out loud.

And the second question: “What would help you feel secure, without requiring me to erase my past?” This invites collaboration instead of defensiveness.

You can also offer a boundary that doesn’t require tossing your mementos: “If looking at the boxes bothers you, I’m happy to store them somewhere out of sight. I’m not attached to having them accessible — just to not pretending those years never existed.”

She may surprise you by softening once she feels understood, not overridden.

But here’s the crucial thing: Memory isn’t the enemy of commitment. In fact, people who can reflect on their past tend to be better at choosing present partners with intention. You didn’t hide the box. You didn’t lie about it. You didn’t turn nostalgia into a secret ritual. Those are the behaviors that signal danger — and you’re doing none of them.

If your girlfriend ultimately needs you to destroy these artifacts to feel loved, that’s not about the photos. That’s about a deeper fear that no amount of shredding will fix.

Your past is a map, not a rival. Stay compassionate, stay honest and stay rooted in the present you’re actually building with her.

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