Senior grey-haired woman wearing casual clothes and glasses winking looking at the camera with sexy expression, cheerful and happy face.

Is it possible to be in mourning for a fantasy that will never be fulfilled? I’m a 44-year-old cis het man, and since hitting puberty I’ve fantasized about sleeping with an older woman — like, a much older woman. The fantasy was always about the mature older woman and, well, that younger and more virile version of me at 18. But it never happened. I got married right out of college, got divorced young and quickly married again. 

Now that I am solidly middle aged and in a monogamous (and very happy) relationship, not only has the prospect of realizing this kink most likely ended, but I am finding it increasingly difficult to even fantasize about it anymore. I’m just too old to have this sort of situation be a realistic scenario. I’m not finding an older woman to sleep with anytime soon, and I’m not magically turning back into a 20-something anytime soon. Knowing that I’ve aged out of my ultimate fantasy without ever acting on it makes it almost sad to think about. 

I’m not asking you that dumb and obvious question (“Is this normal?”), as I’ve been reading you long enough to know the answer to that. I guess what I’m asking is for advice on how I can deal with the sadness I’m feeling about this.

— Often Life Disappoints

Seeing as you’re mourning a fantasy that will never be fulfilled — you’re never gonna be a young stud seduced and/or seduced by a mature older woman — the answer to your first question (“Is it possible to be in mourning for a fantasy that will never be fulfilled?”) is obviously yes, OLD, as demonstrated by your own feelings of grief. 

As for what to do about the sadness you’re feeling, well, you did something very useful with your sadness today by writing to me. While it may be too late for you to do something about your fantasy, your letter will hopefully inspire others — young and old alike — to act on their fantasies before it’s too late, e.g., before they’re too married and/or too monogamous and/or too old. And here’s a fantasy-fulfillment pro tip for them: creating opportunities > seizing opportunities.

And you’re not actually too old to realize this fantasy, OLD! While you can’t play the young and virile stud for a 50-year-old woman — you need that age gap to gape — you can play the younger and still virile stud for a woman in her mid-60s. 

To do it the right way, i.e., to do it without being a cheating piece of shit, OLD, you’re gonna need your wife’s permission. If your wife is one of those insecure, irrational people who expects all of her partner’s sexual thoughts and fantasies to revolve around her, then she’s unlikely to react positively to your request for a hall pass. But if your wife doesn’t expect all of your sexual fantasies to revolve around her — if your wife doesn’t have a problem with you looking at porn; if she doesn’t get angry when she notices you noticing the host barista — getting a little tipsy and/or high together and having a conversation about your sexual fantasies and hers (AND HERS AND HERS AND HERS) might get you that hall pass.

P.S. Go into that conversation prepared not just to ask for a hall pass, OLD, but to offer one.

P.P.S. And if your wife’s been fantasizing about fucking some young stud … Yahtzee! 

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