This is the tenth installment of Higher Gossip, an advice column on sex and love. Read previous installments here.

Q: I got divorced during the pandemic, after an eighteen-year marriage. For the past couple of years I’ve had a fun time having lots of romantic adventures. I’m 55, and the average age of people I date is around thirty, with a few years leeway on either side. This is okay for short-term romances—I’ve had connections that are in many cases deep and meaningful.

But I’m starting look for something more like a long-term partner, and I’m confused. I feel like it’s going to be hard to build a long-term life partnership across these sorts of age gaps. I’m a bit ashamed about this: on the one hand, I want to allow myself to be attracted to whoever I’m attracted to, and being attracted to young pretty women seems like the most natural thing in the world. I don’t think that what’s at work here is some sort of power dynamic thing. I think I’m just sexually attracted to women who are conventionally hot, and that tends to mean “not 55.” But it somehow feels, I dunno, out of keeping with my largely feminist values to be so unattracted to women closer to my age.

A: Your question, which I appreciate for its rare frankness, has two important elements: on the one hand, is it anti-feminist to be attracted to young, pretty women, and to consider women who are 55 not conventionally attractive? And on the other hand—whether or not it’s anti-feminist—what are you going to do about trying to find a partner who actually suits you, if you aren’t attracted to the ones you imagine are suitable?

Let’s start with the problem of feminism. There are lots of women who would read your question and call you a jackass and a misogynist for not being attracted to women your own age. Presumably you know that, and that’s why you feel guilty about it. Of course, you’re trapped; except for those rare people who are immune to vanity or have a particular penchant for older women, we are all mere foot soldiers long since drafted into a youth-focused sexual culture. We are all attracted to young, pretty women, and we needn’t be ashamed about it. Undermining your own appreciation for beauty seems like a very dull and futile way to get on in the world. The underlying question is: Should you be ashamed of dating young pretty women, when you yourself are no longer young and pretty? Unless you’re dating underage girls, which it sounds like you aren’t, I don’t think so. Adult women, even those 25 years younger than you are (as I am myself), have eyes in their heads and perfectly reasonable judgment about their personal lives. There are plenty of reasons why the women you date are attracted to the fact that you’re older. Whether or not I believe that it isn’t a power dynamic thing is irrelevant; if it is, and you both like it, so what?

The more pressing problem in your taxonomy of your attractions is: What is it like to not be attracted to women your own age? I imagine it’s troubling. There are the feminist reasons to be troubled—you worry there’s something wrong with you, that you’re a misogynist and a jackass and that you must only care about women based their looks, which, by the way, I don’t think is true—but there’s also a different sort of lack. Wistful, discomfiting. Or maybe I’m speaking for myself. I’m also a person who is attracted to women. I, too, look at older women and consider whether I’m attracted to them. Often I am; I think there’s a sort of flavor to lesbian culture which has encouraged me to relish the look of power and experience in a woman. The sexual culture you live in as a 55-year-old heterosexual, needless to say, has not encouraged you to relish that look of power and experience. Some men are attracted to it anyway. Not everything is accounted for by decades upon decades of film and advertising. But we do frequently, and fairly, feel robbed of some vastness of attraction or curiosity by our reductive sexual training. We wish we had more of a natural appreciation for what we know is lovely—the look of wisdom, or the look of taste honed over decades, or the look of a body maturing. We wish we were shown these things in the context of sex more frequently. We wish the burden of cultivating satisfying and non-superficial attractions, like so many other burdens, was not placed solely on us. I actually wrote a novel about (to my mind) how exhausting and futile it can feel to try to align our attractions to our values. I feel you.

Let’s talk, for a moment, about finding a love that will suit you, because I think the two parts of this problem will soon converge. In April I had a question from someone with a similar dilemma to yours. The writer felt disheartened because they had started to suspect that all the women of “their type” that they pursued or liked on dating apps must, in fact, be wrong for them, since dating these sorts of women had always gone wrong in the past. I found their question—Can we ever trust ourselves to know what we want in a lover?—very moving. In that column, I outlined what I think are the two practical logics a person might follow in the face of this mystery: On the one hand, you might decide that you’re the primary enemy of your own happiness, that your own instincts are leading you superficially toward people with whom you can’t build a good life, and therefore that (in your case) you should start taking chances on women your own age to whom you’re not especially attracted, since it might turn out that actually one of these women is perfect for you. On the other, you might decide that your instincts are more trustworthy than your rational theories, and that you would do best to pursue women to whom you’re attracted, not worrying about the details, and come what may. It seems as though you’ve taken the second road so far, and though pleasurable, it hasn’t led you quite where you want to go now.

I’m going to take a leap and say that I don’t think it’s worth much to go out with women your own age who you don’t currently find attractive. I don’t think one finds a great love that way, and I don’t think women appreciate being taken out by men who aren’t attracted to them. I do think it’s possible that you might form a sustainable relationship with a much younger woman. Despite all the predictable problems—stages of life, health discrepancies as you age, social discomfort around your age gap—people do it all the time.

It feels as if your marriage is an important touchstone here, though you’ve told me little about it. Perhaps the tensions that led to the end of your marriage are influencing the type of relationship you want to have now; I wonder if they might be informing the age question too. Since you don’t mention any age gap between you and your ex-wife, I assume you were relatively close in age. You grew older with her over nearly two decades of life, an experience in which I imagine your attraction to her must have played some important part. Did you remain attracted to her? Did you notice changes that attracted you more, or less, as she aged?

My impression is that, after spending eighteen years with one person, the freedom of divorce has naturally made you interested in those women who are most different from your ex-wife, women who are entirely fresh and strange in all kinds of ways. That makes sense to me. I think, in certain respects, it’s liberating and wise. But, at the risk of sounding like I’m saying “you can control who you’re attracted to,” we do have a sort of directorial power over our attention. We are often attracted to older people as we ourselves age—and as the people we love age with us—because the qualities we naturally pay attention to have shifted. This process has been interrupted for you by the grief and inspiration of divorce; yet it sounds like you’re growing tired of novelty, and you’d like to return to your own fold. You clearly still have an appreciation of the qualities, held in common with you, which a woman closer to your age would bring to a relationship. There must be many women in your acquaintance close to your own age—I don’t mean available ones in whom you might be interested, but simply women in their forties and fifties who exist around you—that you admire: their sense of style, their intelligence, whatever it is. Perhaps I’m naïve to say this, but I do think that by paying attention to what is relevant and interesting to you—in this case, women in your stage of life—you might find that your estimation of what is attractive is pried, bit by bit, out of the tyrannical hands of youth.

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Q: I fantasize about a coworker. A dream I had about him flipped an unsuspected switch. For the last year I’ve been plagued by (or indulged in) daydreams of him. In real life, he’s happily married, I’m happily married, and chances are we’ll work together for years to come. On the upside, a crush heightens sensation; insignificant interactions burgeon with meaning. Maybe the trigger is the dispiriting thought that no one except medical professionals will ever discover my naked body again, nor I discover anyone else’s.

I’ve always thought of fantasy as preparatory to reality: one should realize it, actualize it, get something out of it. What good is fantasy, if it’s a bad idea to make that dream a reality? Why can’t I fantasize about some more appropriate target?

A: I recently re-encountered an early episode of Sex and the City in which Miranda, after finding spanking porn in a man’s apartment after only a few dates with him, tries to flirt with him by offering him a good spanking; the relationship ends, as those on Sex and the City so often do, with him never calling her again. (At this stage in phone history, there’s something romantic about this once-devastating phrase, isn’t there?) Like most morality plays on Sex and the City, this plotline seems intended merely to remind us that the available men in New York are trash. But it could instead serve as evidence of the fact—which we find it so difficult to accept—that there is a very hazy, nonlinear relationship between what we like to think about doing and what we actually want to do, in the flesh, in our own beds (not to mention as a lesson on the perils of snooping).

There is a commonplace that underlies your question and bears repeating: we want what we can’t have. The more familiar things become, the less strictly erotic we find them. Let’s say you begin an affair with your coworker in which the very fantasies that have haunted and thrilled you are played out, with all the heights of pleasure you associate with them. Whether you exhaust the limits of the affair, in months or years, or whether the two of you leave your happy marriages and start a new one, the erotic fantasy will end. This is not to say that you might not have a happy life, even a better life, with your coworker, though from your question I don’t think you imagine you would. This is just to say that once your coworker has become yours, the thought of him will no longer hold the same forbidden thrill. Desire that is easily, regularly gratified barely even registers as desire.

We know this well; yet some part of you does not actually believe it, because you still ask: Why can’t I fantasize about some more appropriate target? This is like asking, Why can’t I be free of desire?

The claim I found most provocative in your letter is that when it comes to fantasy you believe “one should realize it, actualize it, get something out of it.” You assume here that we don’t get anything out of our thoughts, that we only get something out of what happens to us physically. Not only do I think you’re wrong, I don’t think even you believe that the sole purpose of fantasy is to bring a scene into reality. After all, you admit readily that your crush on your coworker heightens your sensations, makes banal interactions “burgeon with meaning.” You relish the way your fantasies are working on you—the fact that your thoughts are sensational in themselves. You’re half-aware of this. Something fantastically exciting is in fact already happening to you, and yet you fixate on what isn’t happening. But it’s important to keep in mind just how enormously generative having a fantasy, merely a fantasy, can be, even if it is not realized. I’m sure you’ve heard that factoid that we get more out of anticipating an upcoming vacation than we do from actually traveling. I think we often get more out of lingering on a fantasy for hours, days, months, than we do from putting it into practice.

You don’t want to be free of longing, not really. What you want, instead, is to experience fantasy without shame. “Inappropriate” and “shameful” are, I think, almost always synonyms. And why is it that you’re ashamed? In a sense—though there are plenty of details you aren’t telling me—yours is the most universal, the most sympathetic fantasy of release from occasional marital monotony. At home, to your spouse, you represent your entire accumulated life as witnessed by a single biased person; at work, to your coworker, you’re an independent, complex, lighter version of yourself, untethered and competent, a version from which still seem to flow all sorts of possibilities. What could be more erotic? I’d venture to guess that every happily married person fantasizes about people they would call “inappropriate targets,” and almost all of them in settings in which they feel close to how they felt when they were younger and unmarried, when life was simultaneously mystifying and uncomplicated. I suppose what makes this fantasy inappropriate or shameful isn’t that your coworker is terribly ugly, badly behaved or even your subordinate, but simply the assumption that monogamy applies not only to the flesh but to the mind. Personally, I was raised on the advice of Dan Savage, who advocated to those indulging in inappropriate crushes and flirtations that they enjoy those thoughts and then bring that sexual energy back into the marital bedroom—which I continue to find the wisest take on monogamy I’ve ever encountered.

A person we desire is not only a person but a vessel. We feel selfish admitting this, but we would do well to be frank about it. Your coworker is both a person in his own right and a symbol of some version of yourself or your life that is otherwise missing, and which his perception of you gratifies. In February I wrote about an affair I’d had, while I was with my college boyfriend, with a woman named Noa. During this affair, I didn’t really consider leaving my boyfriend, because I told myself the same things I’m telling you—that I would fantasize all my life about whatever was “inappropriate” or out of reach, and I would be stupid to cause trouble on the basis of little more than an ego-indulging fantasy. I felt as if it took me many miserable trials, and reading some psychoanalysis, to recognize that a fantasy is an indispensable piece of information about what is missing or wrong in one’s life. This might sound like an endorsement of your belief that fantasy is preparatory to reality, but that isn’t what I mean. What I mean is that there is a relationship—but an indirect one—between your fantasy and your reality. My fantasy about Noa was not working to inform me of some reckless penchant for novel sexual experience, as I imagined it was. What I actually wished for had nothing to do with sex, despite the fact that sex symbolized it; I wanted to feel much safer and be treated much more sweetly that I ever had been. From the framing of your question, and your assurance that your marriage is happy, I’ve assumed that your coworker fantasy is of the more standard midlife kind—a wish for the opposite of safety and sweetness, for erotic novelty. But of course I don’t know. I stayed with my college boyfriend while I was fantasizing about Noa, because I, too, would have described our relationship as happy. Perhaps a more specific criteria with which to evaluate your marriage, rather than happiness, is what it provides you and what it lacks.

To return to that episode of Sex and the City, the most obvious overstep Miranda makes isn’t assuming that her boyfriend wants to be spanked, but that it’s too early in their relationship to invade such a private area of this man’s psychology (and his apartment). I’ve argued that the relationship between fantasy and what we want to do in reality is oblique; but even more importantly, and more obviously, fantasy is extraordinarily intimate, no matter what it signifies. I know little about your marriage, but if it is in fact happy, I hope you and your spouse are intimate enough with one another to talk about your fantasy. Nothing is quite so shame-relieving as this. Perhaps you’re afraid of provoking jealousy, but then again, jealousy can be a wonderful engine in a relationship.

If all this interrogation about what your crush actually signifies is beside the point, and you’re confident it comes down fundamentally to your fear that your body won’t ever be encountered again for the first time, I hope it isn’t too trivial of me to recommend one of my favorite games to play in a long-term relationship. I call this game “first kiss.” It’s exactly what it sounds like: pretend it’s your and your spouse’s first kiss. No, it’s not like the first time. Still—it’s pretty fun.

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