Dear Bess: “My wife would laugh at my date choices – is it crazy that I still hear her voice?”

Dear Bess,

My wife passed away a few years ago from cancer. It was a terrible time, but I’ve slowly found my way back to living – including, tentatively, dating again. I’ve noticed that being a widower rather than divorced seems to work in my favour with women I meet. Is that actually true, or am I imagining it? And here’s the thing I haven’t told anyone – my wife would absolutely laugh at some of the women I’ve been on dates with. I can almost hear exactly what she’d say. Is that a little crazy?

— Tom

Dear Tom,

Not crazy. Not even slightly.

Let me start with your wife, because she sounds wonderful, and because I think she deserves to be at the top of this letter rather than tucked away at the end like a footnote. The fact that you can still hear her voice – that you know instinctively what she’d make of the woman who talked about her crystals for forty-five minutes, or the one who ordered an entrée and then announced she didn’t eat carbs –  that is not a sign that something is wrong with you. That is a sign that you had a real marriage. A deep one. The kind where two people become so fluent in each other that the conversation doesn’t entirely stop just because one of them is no longer in the room.

Carry that voice with you, Tom. It sounds like excellent company.

Now, to your question about being a widower versus divorced – and yes, you are not imagining it.

There is, among women of a certain age and experience, a quiet but real distinction made between the two. A widower signals something specific: that you were chosen, that you stayed, that the marriage ended through grief rather than failure. It suggests, rightly or wrongly, that you know how to love someone over the long haul and that you weren’t the one who walked away when things got hard. Divorce, of course, tells its own complicated stories – many of them entirely sympathetic – but it comes with questions attached. Widowhood tends not to.

None of this means divorced men are at a disadvantage, nor that being a widower is some kind of romantic credential you’ve earned. But you asked if it’s true, and honestly? It probably is. Women who’ve been through difficult divorces or who’ve watched friends navigate them can find something quietly reassuring about a man whose marriage ended the way yours did – not through incompatibility or betrayal, but through terrible bad luck.

What matters more, though, is what you do with it. Being a widower opens a door. What you’re like when you walk through it is still entirely up to you.

One gentle thing worth sitting with: the women you’re dating are also, presumably, full human beings with their own histories, their own losses and their own excellent qualities – even if your wife would have had something pithy to say about a few of them. The inner commentary is fine, Tom. It’s human. Just make sure it doesn’t become a barrier. Nobody new will ever be her, nor should they be. But someone new can still be rather marvellous in their own right.

The fact that you’re dating at all, that you’re re-engaging with life and with other people after real grief, says something good about you. And the fact that your wife is still in the room with you – laughing, rolling her eyes, keeping you honest – says something good about the marriage you had.

She sounds like someone worth listening to. Even now.

Warmly, Bess

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