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Ask Anna: I still think about my ex years later. Should I contact them?

Anna Pulley, Tribune News Service on

Published in Lifestyles

Dear Anna,

A few years ago, I fell into an intense long-distance relationship with someone I met through a fandom community. We went from friends to lovers, writing smutty fan fic together and talking every day. They already had a long-term partner, and although they had always considered themselves open, I was the first person they had actually pursued outside the relationship. I’d been polyamorous for over a decade, so there was a significant difference in experience.

For the first several months, things felt wonderful. I got along well with their partner, everyone seemed communicative, and we were falling in love. Then a major conflict arose after we had video sex that involved a level of nudity their partner didn’t realize had happened. We also had a different sexual dynamic. They were a stone top who didn’t often get fully undressed for sex with her and was always focused on her pleasure. Our dynamic had become one where they felt submissive to me and very into the concept of me topping them and showing me all. I knew this might create some hurdles but had repeatedly checked that everything was cleared beforehand, so I felt blindsided when it became a problem.

I spent a lot of time trying to support their relationship and repair the situation. I even asked to speak directly with their partner because I wanted her to know I had never intended to cross a boundary, but they refused. Eventually they took space to work on things together while I waited on the sidelines, and the dynamic began to feel increasingly painful and unequal.

We ultimately broke up, but it was one of the most beautiful breakups I’ve ever had. There was genuine love, gratitude and mutual respect. We agreed to take some space and reconnect later.

Then, a few days afterward, they sent me a Google Doc containing a letter from their partner about how she had healed from the situation and how their relationship had grown stronger. Included was the revelation that she had actually wanted to speak with me at the time — something I had repeatedly requested and been denied. The whole thing landed badly. I had already told them I felt like I was prioritizing their relationship over my own needs, and the letter made me feel more like a lesson in their growth than a person they loved.

When our no-contact period ended, I sent a long, thoughtful message explaining why it hurt and saying I’d be open to reconnecting in the future if trust could be rebuilt. They replied only, “Take care,” and then blocked me on social media.

Years later, I still miss them. I don’t regret my message anymore; I think it was mature and fair. But I’ve never understood why someone who seemed to love me so deeply cut things off so completely.

I’m considering reaching out. Part of me genuinely wants to know how they’re doing. Part of me wants closure. I also don’t want to reopen old wounds or cross boundaries, especially given the history with their partner.

Should I contact them? If so, what’s the best approach? — Ready for a Shift

Dear RFAS,

I think the first question here isn’t Should I reach out?

It’s What am I hoping will happen if I do?

And I don’t mean that cynically. I mean it literally.

When people say they want closure, they often mean a dozen different things. Sometimes they want answers. Sometimes they want forgiveness. Sometimes they want confirmation that the relationship mattered. Sometimes they want the person back. Sometimes they want one last emotionally satisfying conversation — to make up for previously crappy or hurtful ones, or to have a clarifying arc that helps the whole story make sense.

So before you draft a message, get very very honest with yourself. If they responded tomorrow, what outcome would feel meaningful? And maybe more importantly: How would it feel if you didn’t get a response that’s meaningful? Or a response at all?

Would you be satisfied with a brief, warm exchange that goes nowhere? A friendship? A rekindling of your joint smutty stories? An explanation for the blocking and the silence? An acknowledgment that they handled the ending poorly? The possibility of rebuilding something? Knowing the answer doesn’t mean you’re demanding it. It just helps you understand what you’re actually reaching for.

Because from where I’m sitting, the thing that stands out is that you’ve already had a lot of closure.

You had the “beautiful breakup” conversation. You expressed your hurt. You told them exactly what impact their actions had on you. You left the door open. They chose not to walk through it.

That doesn’t mean the ending felt good. It doesn’t mean it felt fair. But it does mean that the absence of closure may not actually be the problem.

I wonder if what’s hurting is the absence of understanding.

 

You never got an explanation for the abruptness. You never got a satisfying answer to the question of why someone who seemed to care so deeply could retreat so completely. That’s a very different ache.

The hard truth is that reaching out may not soften it.

They may not respond. They may respond in a neutral or cold way. They may be happy to hear from you. Or less happy. They may have built a life where revisiting the chapter of you no longer feels possible or desirable.

And even if they write back, there’s no guarantee they’ll provide the explanation you’ve been carrying around all these years hoping to find.

That said, I’m not against reaching out. And I’ll be honest: I’m pretty baffled about that letter they sent you post-breakup. Maybe it was intended as reassurance. Maybe it was an awkward attempt at transparency. Maybe it was the closest they could get to giving you the conversation you’d wanted all along.

What makes the Google Doc particularly painful is that it didn't just hurt — it retroactively complicated something you’d found peace in. You had a beautiful breakup! That is so rare and magical! You’d done the hard work of ending things with love and mutual respect, and that was real. The letter didn't just reopen the wound; it reached back and unsettled the one thing that had felt nice in this ending.

Sending someone a document about how much stronger their primary relationship has become after breaking up with you is, at best, a spectacular misread of the moment, and at worst, a message that centered someone else’s healing at the expense of yours. I don’t know what they intended. I do know why it hurt. The message you received wasn’t, “You mattered to us.” It was, “Look what we learned!”

It’s also worth noting that you came into this with a decade of polyamory experience, and they were navigating it for the first time. That gap doesn’t excuse the messiness — the crossed wires, the partner’s unexpected reactions, the clumsy letter—but it may help explain it. New relationships to non-monogamy can produce a kind of tunnel vision, where the primary partnership becomes the only lens through which everything gets processed. That’s not a defense of how they treated you. It’s just one possible answer to the question you’ve been sitting with, which is:

Why did someone who seemed to love me handle things so poorly?

And then there’s the blocking. Being blocked after sending a thoughtful, measured message — after showing up with maturity and vulnerability — is genuinely painful, not just confusing. It’s the kind of ending that doesn’t offer you anything to hold onto, and it makes sense that it’s stayed with you.

But it’s worth remembering that people block for all kinds of reasons that have nothing to do with the person on the other end. Sometimes it’s self-protection — a way of closing a door they’re afraid they’ll want to open. Sometimes a partner requests it, or it’s part of an agreement they’ve made together. Sometimes grief makes people do blunt, unsophisticated things, and blocking is easier than sitting with the complicated feelings that come with staying connected. None of that makes it less painful. But it does mean the block probably says more about where they were than about what you meant to them.

In any case, years have passed. You aren’t contemplating contacting someone who asked never to hear from you again. You’re considering a single, respectful message to someone who once mattered enormously to you.

The key is to send it only if you can genuinely tolerate any outcome. And I mean any.

Including silence.

Including kindness without reconnection.

Including discovering that the version of them you’ve been carrying in your heart no longer exists.

If you do write, keep it simple. Don’t lead with history. Don’t interrogate the breakup. Don’t ask them to explain themselves. Just say you were thinking of them, hope they’re well, and would enjoy hearing how life has treated them if they’re open to it.

Then let them choose.

Because I think the real shift you’re looking for may not come from finally getting closure from them.

It may come from accepting that you’ve already said everything you needed to say — and deciding whether you’d like to open a new conversation rather than finish an old one.


©2026 Tribune Content Agency, LLC.

 

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