Is There Real Potential With This Ex?

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Dear Meredith,

I first came across Love Letters through your podcast in March. I was living outside of the U.S. for work when, due to the pandemic, I had to pack up and travel back home to the Boston area in about 48 hours.

I’m in my early 30s, divorced (from a serial cheater), and I haven’t had any truly significant relationships since my divorce was finalized five years ago. But I haven’t been celibate either. I’ve dabbled in dating, including using dating apps (which I despise), but I’ve never really clicked with anyone, probably due to a combo of not being emotionally ready, not putting much effort into the process, being quite busy with my professional life, and just the luck of the draw.

Also, I still fantasize about a previous love – the relationship I was involved in before the relationship that resulted in my marriage/divorce (to be clear, this fantasy is not a COVID-related “should I contact my ex” thing, although maybe that is in the mix a little too).

We met as co-workers and then connected in a way I’ve never felt before or since. The thing is that we didn’t actually spend all that much time together. We met in June, in August he went on a long trip (I joined him for about two weeks), we kept in touch by letters mostly, then we were together for about two months before I left the country that February to work abroad for a few years. We tried to stay together, but I ended things between us about six months into the distance. I was about 10 years younger than him, and it seemed unrealistic to try to maintain this relationship then. We stayed friends and are still in touch, with communication waxing and waning. We’ve seen each other in person a handful of times over the last 10 years, but never anything romantic. Recently we’ve started communicating by phone more frequently. I think he might be open to a rekindling, but I care too much about him to go down that avenue when I’m not clear about my own wants/needs. And yet the fantasy remains for me of our relationship. I don’t know if the fantasy is about actually being with him, or if it’s about that sense of wonder, of open horizons that I felt with him in my early 20s.

Am I clinging to an immature dream because it is more comforting/romantic than trying to find an actual partner in the here and now? Or is there still a connection to be explored with this man and I should ignore the voices telling me that is unrealistic/what my romantic life should look like? Is it just easier right now with COVID to fantasize about someone currently living several hours away than actually putting effort into finding a partner where I live? I guess I wonder if the fantasy is all it needs to be – or if I want to explore it in reality.

– Wishfully wistful


I don’t see a major downside to this communication. If the worst-case scenario is that you realize, over many conversations, that this has been about nostalgia and COVID-19 boredom, you’ll have answered a long-standing question. But if you decide it’s more – that a decade later, you have a ton in common and want to reconnect – that’s even better. Assuming you can get to each other (eventually) with tests, precautions, etc., how great that you found each other again.

It’s not as though you’d otherwise be dating with ease. It’s also not one-sided. So many of our “Why can’t I stop thinking about my ex?” letters are from people whose past loves have no interest in this kind of communication. Your ex is game for these calls. He’s engaged.

I would recommend that if this connection becomes part of your routine – if it grows to be a significant, intimate part of your day/week – you stop to ask him what he thinks of the potential here. He might not have definitive answers about what comes next, but he can tell you whether he’s hopeful for more.

Try not to guess the end of this story before you have all the information. Accept that you have little control right now. You’re having an experience. Let it play out.

– Meredith

Readers? Is this wishful thinking or something with potential? Does it matter what it is at the moment?

Love Letters

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