What Was He Up To?

Coupled but it’s complicated? Single and stressed? Have a question about your love life or lack thereof? Submit your own question here. You can also email [email protected].


A few years ago I received a surprise letter from a high school boyfriend with whom I’d lost contact after college. He wanted to reconnect with “the wonderfulness of a special friend.” A flurry of emails ensued; he’d been divorced and has been with a “wonderful woman” for the past several years. I’d been widowed. Warm and friendly birthday and Christmas cards followed, and then he suggested we meet to celebrate our decades-long “forever friendship.” I arranged for lunch and for the tab to be pre-credited to my card; it’s my town, I told him, and thus my treat.

Our in-person conversation, while pleasant, was somewhat strained and pedestrian, perhaps because the preliminaries had been covered via email. But also … could it have been that there wasn’t a clear way forward given what he told me about his relationship status? Late in the lunch, he once again, albeit briefly, referenced his “girlfriend.” In other words, I’ve wondered why he reached out to me in such a personal and inviting way to begin with. I certainly wouldn’t have done so if I were coupled. Nor can I imagine my late husband putting pen to paper to deliberately contact an old romantic interest.

I’ve had lunch and dinner with any number of men over the decades, but these were always business meetings that, if and when they blossomed into friendships, would evolve to immediately include our significant others. Similarly, a friend of mine recently got a call from a romantic interest from decades past, but this man was divorced and available. He had reason to believe she was as well. They are now married.

This is different, and I would be interested in what you make of it. Does it seem odd, given that he is involved with someone, that he would contact me, pursue the email exchanges, and suggest that we meet socially without her? Could I have somehow been at fault? I do confess to being somewhat flattered and intrigued by the reappearance of someone I knew and liked back when the world was young and fresh. If he were available, I would have taken the conversation in a very specific direction. But because he isn’t, should I have responded in a different way, or not at all? Finally, and most importantly, where next? In parting, he said for us to be sure to do it again in another five decades. Oddly, he didn’t thank me for the lunch, either verbally or via email. His birthday is coming up. Do I send a card? I don’t want to be obvious about cutting off an old friend who is essentially a very nice guy. But as with our conversation at the lunch, I’m not quite sure where, if anywhere, to take this.

– Old friends


Skip the birthday card. You didn’t enjoy yourself at the lunch, and you know you’re not looking to see him again. He didn’t thank you for your time or the meal (rude), and the “let’s see each other in fifty years” joke (if it was a joke) didn’t land after the awkwardness of the outing. This man is a “forever part of your history,” not a “forever friend.”

Why did he reach out with a “flurry of emails” if he’s in a relationship? Well, maybe he’s having trouble with his current partner and wanted to see what else was out there. Perhaps he showed up to the lunch and remembered that he can’t get into a time machine and become a high school kid again.

Email and texts leave room for fantasy. An in-person meal forces you to consider what you’re actually trying to do.

I would guess, for the record, that he’s feeling his age, wanted to connect with someone from his past, liked your attention, and then, in person, things felt more strained – and inappropriate. He might have gone home and thought, “Wow, what have I been doing?”

Instead of figuring out what he’s been up to, focus on yourself. You ask a good question: what were you up to when you got deep into this correspondence? I’m not saying the end result is your fault, but I do wonder if this was all practice for whatever romantic relationship might come next.

If this taught you that you’d like to reach out to some single people, go for it. Learn the lesson and seek out those who are available.

– Meredith

Readers – have you reached out to someone from your past like this? What were your expectations and motivations? If someone reached out to you with a flurry of emails, what would you assume? Share your own experiences, please. Also, if he starts up contact again, what should the LW do?

Love Letters

What’s your love and relationship problem?

Ask Meredith at Love Letters. Yes, it’s anonymous.

About Love Letters