Dear Playboy Advisor: My Partner Makes More Money Than Me, and It Bothers Me

IMAGO / Zoonar


I’m a woman in my early 20s, in a relationship with a man in his mid-40s. I’m not concerned about the age difference, but the financial difference is dramatic. I live paycheck to paycheck; he makes seven figures a year. Whenever he takes me out, I can’t afford to go 50-50. As a feminist, I feel infantilized having an older man pay for everything. How can I feel like I’m contributing equally?

Contribution is about value; it’s not only about dollars. You may not be able to afford a fancy meal, but you can invite him over and cook, no matter how small your space, or you can say, “There’s a nice taco truck down the street.” Evenings like those can be just as exotic and fun as dinner at a Michelin-starred restaurant. It’s about the gesture with which you say, “I too can contribute to our relationship. I love to give you things, even if it’s not half the check.”

Egalitarianism isn’t always symmetry; complementarity and fairness are the goals here. So whatever you do, don’t let the discrepancy between your bank accounts keep you from taking any initiative because you think that what you have to offer isn’t equal in amount. It’s equal in meaning. (For his part, don’t forget that he knows who he picked.)

You mention you’re a feminist. What I make of that is that somebody may have told you that an older man shouldn’t be paying your way. That’s a ready-made idea. Why can’t a feminist be taken care of by a man—or a woman, for that matter? It doesn’t mean you don’t have your own means. And you’re in your early 20s; this is a developmental situation translated into an ideological one. (When you’re 46 we’ll discuss it again.) I wish for you to find myriad ways to express your identity, your feminist ideas and your feelings for this man.

If they could do some simmering, kissing, stroking, turning on and then leaving, staying turned on and falling asleep in a state of arousal, they would love it.

What advice would you give to straight men who want to be better in bed?

Good sex is far less about mechanics and performance and far more about erotic intelligence. That’s why the number one thing is this: Slow down. Don’t go instantly looking for the spot—the genitals, the butt, the clit. Know that foreplay is not five minutes before the “real thing”—penetration, orgasm (often only yours) and then sleep. For many women, the real thing includes everything before and after, and what’s between her ears matters as much as what’s between her legs. Understand the erotic power of words and that when the lips around the mouth open, so will those other lips you’re so interested in. (Know also that a great kisser is irresistible.)

This might surprise you, but don’t go specifically chasing her orgasm. Your ability as a lover is not measured by her ability to peak. Erotic highs are as much about pleasure and excitement as they are about coming—and nothing is more of an orgasm killer than pressure. She’ll fake it just to cut the pressure short, and you will never know. So focus on pleasing her. What she enjoys is your attention on her, your desire for her, your lavishing and ravishing her and making her feel irresistible. It’s in these moments that women feel they can let go and enjoy themselves.

Here is something else I want you to know: Desire isn’t just this spontaneous thing that sweeps over you in an irresistible wave. There are many ways for women to engage in sex. Sometimes she’s aroused, other times she has desire but isn’t yet turned on, and then there are the times when she’s willing, not because she’s hot or in the mood but simply because she’s open to see what will happen. For women, sexual desire can be responsive like that. And sometimes they anticipate pressure from you even when it’s not there, so if they touch you and you get turned on, they worry they’ll have to go all the way—before they’ve decided if they want to. If they could do some simmering, kissing, stroking, turning on and then leaving, staying turned on and falling asleep in a state of arousal, they would love it. And if you really want to be a better lover, keep that in mind.

I’ve seen many people fantasize about things they would never dare do in reality.

It’s hard for me to witness my partner’s many fantasies about other people. What am I supposed to make of this?

There are really two questions here: one about the nature of fantasy and another about what your partner’s fantasies mean to you and about you. These have very different answers.

To address the first question: If you really want to know what people are longing for in sex, look at their fantasies. Fantasies express some of our deepest emotional needs in the language of sex. But they’re not simple; they’re like dreams that have to be decoded. If you can find the curiosity to engage in a conversation with your partner about his fantasies, you may find yourself having one of the most fascinating chats two people can have.

And then there’s the question of you and your feelings. Does it seem as if your partner is being secretive in his erotic imaginings, or does your discomfort result from a lack of confidence on your part? Some people interpret their partner’s fantasies as a statement that something is lacking, but you could very well be included in the plot. And while the modern romantic ideal suggests that we should be able to fulfill all our partners’ erotic needs, that’s not necessarily the case. Either way, fantasies about others don’t mean you’re not loved or desired. Our erotic mind is a place where we often find the freedom to let our imagination roam. There can be something playful and deeply satisfying for both partners in exploring that.

So what can you do to feel more comfortable with your partner’s fantasies? First, be honest with yourself: Do you ever have fantasies about anybody or anything else? Then, here’s how I would broach it: You can tell him that the very thought of him imagining himself with other women makes you question the security of the relationship. Try to acknowledge your fear without turning it into an accusation that there’s something wrong with what he does. Use that as a starting point to figure out what belongs to you versus what belongs to him.

From there you can ask him to describe his fantasies and how long he’s been having them. Ask for an invitation to the antechamber of his erotic mind. That place of imaginings is more sacred, more sensitive than any of the orifices we penetrate. Try to stay curious, even if it scares you. One person’s delight can be another’s distaste—that’s in the nature of our erotic blueprints.

As he tells you his stories, remember: Sexual fantasies are not necessarily literal narratives of secret intentions. I’ve seen many people fantasize about things they would never dare do in reality. Understanding the meaning of your partner’s turn-ons is often what makes them less frightening. I could very well imagine you developing a safe space to experience the pleasure of fantasy together—in a way that would invigorate a loving relationship.

My wife wants sex more often than I do. I can’t keep up. Sex has become an obligation, and when I say no over and over, I feel as though I’m failing her as a man. My whole life I’ve been horny, but now I don’t even want to masturbate. What is going on with my sex drive, and what do I do about it?

We have this notion that men should want sex anytime, anywhere, any way—that male sexuality is driven by hormones and no matter what’s happening in their lives they’re always up for it. Women who don’t have desire don’t question their identity as women, and yet men who struggle with desire often worry that they’re not “real” men.

Let’s debunk this myth. For all of us, sexuality is both psychological and biological.

What’s going on in your life can kill your libido. If you’re anxious, if you’ve experienced loss, if you’re depressed or worried about your job—well, are you surprised you may not be so interested in sex? (Some men, but not all, do indeed turn to sex to alleviate their anxieties.) So what circumstances might be affecting your sexuality?

And what’s going on in your relationship with your wife? Has she too bought into the idea that you should come ready for the job, with a penis like steel, prepared to go at it for two hours? Do you feel pressured, by your wife or your notions of manhood, to perform? Or is your challenge about getting turned on? About feeling worthy? About feeling uninspired? Your situation may not be sexual; it could be relational. For most of history, women have resorted to the power of refusal. Perhaps this is what’s happening with you: “If I have to, I don’t want to and you can’t make me.” Consider that your anxieties around sex could be less about your penis and more about power.

My partner sexts lots of other women but never sleeps with them. Is this a form of infidelity?

These days you can cheat while lying right next to your partner in bed, so it’s more urgent than ever that we have these conversations in which we draw the lines of our relationships: what is in, what is out, what is fantasy and what is betrayal. It’s both a negotiation and a conversation that most straight couples don’t have until the shit hits the fan. When there’s a crisis of infidelity, suddenly couples start to talk about boundaries and transgression, privacy and secrecy—when, in fact, it should be a mandatory conversation that unfolds as a relationship develops.

So ask him, “What does sexting mean for you? What does it do for you? Do you like it or do you need it?” When you bring it up with him, pay attention to whether his reaction is respectful and empathetic or defensive. Does he label you “insecure” when it may very well be his own insecurity that keeps sending him back to his phone, hunting for ego strokes?

What’s at stake here is this: Either his flirting will divert erotic energy away from you, leaving you hungry for the attention that he so generously gives to others, or he’s a man who works up his appetite someplace else but comes home to dine on you. Figure that out and you’ll get a sense of whether it’s an innocent pleasure—a reassurance of his sexiness and mojo—or a more nefarious undercurrent that’s destabilizing your relationship.

I want to have more sexual experiences, but I get attached after hooking up with someone, even when it’s just a few times. Is there a way I can get more comfortable with one-night stands?

In the past, people were embarrassed if they had sex. Today, people are embarrassed if they don’t have sex. The judgment has changed, but the tyranny is still there.

Allow me to ask you: Why do you want to have more sexual experiences? Is it because you want to or because you think you should? Even more important: Is hooking up your thing? If it isn’t, simply don’t do it, regardless of the social pressure.

It sounds as though you feel that when you open up sexually, you also open up your heart. So what? That’s actually a nice thing. Sex involves the penetration of boundaries and the exchange of fluids, to say the least; of course one feels a connection. There’s nothing glamorous about trying to make sex meaningless, even if it’s recreational.

That said, if you want to be more playful and uncommitted, you’ll need to be able to ask your partners, “Is this just a one-night stand, or are you open to something else coming out of this?” If they’re just passing by, then you make your decision. If you don’t like it, don’t agonize over the reason—and don’t try to force yourself into something that leaves you feeling empty afterward. We often spend years trying to be who we think we should be before we finally accept who we are.

Continuing to text your ex is not going to help you either.

Last week I started catching up with my ex over text. We broke up more than a year ago, but there was a lack of closure, and a lot of feelings resurfaced. When my current boyfriend of six months was going down on me, I got lost in my thoughts about my ex, and right after I came, I burst into tears. My boyfriend misread it as a monumental moment of intimacy between us, and then he started tearing up because he thought it was so beautiful. I didn’t have the heart to tell him the truth. Was I wrong to go along with it?

No, you weren’t wrong. He has nothing to do with this. If at some point you realize you’re not really in love with him, then you tell him that. Meanwhile, you have a man who had a beautiful response and was moved by how vulnerable you were, and that’s a good thing. I hope you can value that too.

As you may have noticed, I place a lot of emphasis on communication, but I also think wholesale sharing and all-out transparency can be insensitive. Before you tell him about your ex, ask yourself what it would be like for him to live with your confession. Given that he took your tears as a sign of intimacy and vulnerability, he would probably feel humiliated if you told him you were actually crying because you were thinking about your ex. I see no point in telling him. Decide what you want to do—talk to somebody else if you think it will help you gain clarity—but know that your new guy can’t help you deal with the leftovers of your ex.

Continuing to text your ex is not going to help you either. It’s a form of rumination, an unhealthy lingering, that your new boyfriend is probably not going to be able to compete with, and so it’s probably wise to put a halt to it. More than your misinterpreted tears, I’m concerned about the way you’ve recruited your new man for a part he hasn’t auditioned for. Respect both men, and yourself, by dealing with your inner conflict and unfinished business without their help.

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