Sex & The Single Mom

I Am Attracted To Nice Men, But I Do Not Want To Have Nice Sex

How to ask for the rough stuff, because sometimes that’s actually what you want.

Originally Published: 
Sex & The Single Mom

I am a mother of two teenagers, a boy and a girl. I am also very sex positive and have been casually dating for several years since my divorce. Here’s my issue: I am attracted to guys who are very nice in the streets; I just wish they were a little less nice in the sheets.

I think this is related to something that no one is talking about publicly, which is how complicated casual sex has become. First let me make it crystal clear that as a woman who has experienced traumatic sexual experiences in her past, I so appreciate that dating has become far more sexually communicative. #MeToo paved the way for healing conversations that are being had not only with folks my age, but kids my children’s ages as well. My teenage daughter understands the importance of consent in a way I never did. My son does, too, although he feels far more trepidation about dating and tells me that he would never casually hook up with anyone out of a fear of social repercussions that might come after.

Here’s the paradox of dating in the 2020s: Regardless of how old you are, men are far more sensitive to consent, female pleasure, and women’s sexuality, but they are also projecting a lot of what they think women want instead of actually listening to us.

Since my marriage, I have been drawn to nice men who treat me with respect and gentle-ness outside of the bedroom. There isn’t a single man I have dated these last three years who hasn’t gone out of their way to ensure I feel comfortable in a sexual experience. My problem is that what I want outside the bedroom, I do not want during sex. And even when I communicate this to them, I am met with reluctance at best and even straight up, “Nope. Absolutely not, I would never disrespect you like that.” As if I don’t know what I want sexually at 47 years old. Could it be that (some!) men are so afraid to do the wrong thing sexually, they are defaulting to generic all-holds-barred “love making?” In other words, very safe, very vanilla, “have a good day” sex?

I like it rough. Not, like, BDSM forum rough, but not gentle either. I do not want to have sweet, gentle sex and yet, I feel as if I am being denied what I want because it almost feels like men don’t believe that I actually want that?

What advice do you have, if any, for how to convince a man that yes I actually really do get turned on by the occasional ____, ____, and ______. Because I do like that!

Let me start by saying that I get this, completely.

As someone who dates primarily men and who, like you, likes _____ and ______, I have been in similar situations where what I want is more than what the person I am with feels comfortable with. And while some of that is a matter of sexual preference, I have had really vulnerable conversations with men who, after incompatible sexual experiences, wanted to talk about them. Which speaks to the power of this moment and our willingness to hear each other out, which can only lead towards better understanding of each other.

I bring this up because I think sometimes, in the heat of the moment, when we ask to be ______ or _____ or ______, it feels very different than having a conversation about those same topics over coffee. Sometimes the bedroom isn’t the place to actually get comfortable with a sexual topic.

I also think it’s important to remember that the men you are sleeping with have been with other women who might have equated ____ and ____ with assault and abuse. Such was the case in my experience, after sleeping with someone who didn’t feel comfortable having the kind of sex I wanted to have. When we talked about it later, he explained to me that he could never do ______ to me and I explained to him that I totally understood that, but also sexually, I had certain needs and wants and, making love (which also gives me the icks) wasn’t one of them, especially not after one or a handful of dates. Intimacy must be earned, after all.

It is a rare thing to click sexually with someone after one night and most people don’t feel comfortable going all in with a relative stranger.

I also appreciate how you connected your own experience as a woman dating in middle age to your children dating as teenagers. It is a wild thing to date when your children are also dating, and you can see that the same landmines and pressures exist regardless of age and experience. Sexual desire and intimate relationships are often fraught, complicated, and heavy with the baggage of past experience, societal expectation, and the struggle to trust each other, specifically in a post #MeToo world.

I too am extremely grateful for the #MeToo movement, which I believe gave both women and men a new and culture-shifting insight into consent, sexual behavior, and sexual power dynamics. What I am not grateful for was the lack of nuance within many of the conversations. That led to distrust between many people and I have talked about this at length with both men and women, girls and boys.

Those of us who are dating are doing so during a time when a lot of sexual trauma has been kicked up and the dust is nowhere near settled. This moment has emboldened many women to come forward and speak honestly about their experiences, as well as their desires. I also believe it has caused men to step backwards into the shadows of theirs. I think there is a lot of collective shame men feel (with good reason) and a lot of healing that needs to take place within our relationships.

Sex for women and girls has always been risky. How could we not struggle with trusting men when so many of our formative sexual experiences were blatantly non-consensual or questionably consensual? And while the vast majority of men haven’t been called out for assault or harassment, I think many men are afraid that they potentially could be. That if, say, a woman, specifically a woman they do not know well asks to be _____ during sex, she may not want to have been _____ after the sex is over.

Your point about your son’s reluctance to date out of fear is something that does not come as a surprise to me at all and I think a lot of parents who are navigating the world of dating recognize the difference between the boys of today and the boys of our time. When I was in high school, girls bore the brunt of rumors and got the most shit for hooking up with boys (ask me how I know!) while boys got high fives in the locker room.

It sounds to me like you are kicking people out of bed before either of you feel comfortable enough to disclose your true desires.

That is not the case for generation Z and as a parent of both a teenage boy and a teenage girl, I recognize the dynamic shift and its nuanced effects on all genders and the new anxieties relationships cause.

I can understand why young people are far less sexual than we were at their age. The stakes are different and sex is fraught with a new set of cultural, sexual, and social landmines. And while hetero sex has always been ripe with social dangers for girls, the boys of my youth had free range. That is not the case anymore — which is a good thing. But it is naïve not to recognize the ramifications of call-out culture and how that affects trust between genders. Especially when it comes to a certain kind of sex.

Which brings me back to the kind of sex you’re looking to get into. It is a rare thing to click sexually with someone after one night and most people don’t feel comfortable going all in with a relative stranger.

I always say that one should never prioritize their pleasure above another person’s comfort and that goes both ways. Surely, if you want certain things sexually that you do not feel like you are receiving, you should find someone who can give you those things. But it’s also important to listen to your partner the same way we — as women — expect men to listen to us.

And while being respected outside the bedroom should always be a pre-requisite, it sounds to me like you are kicking people out of bed before either of you feel comfortable enough to disclose your true desires. Because wanting a nice man in the streets and a not so nice man in the sheets, is not, as you say, too much to ask. But it is going to take some conversations you must be willing to have fully clothed. Maybe even a few weeks (or months) of dating to gain each other’s trust to get there.

And a little grace for everyone involved.

I want to answer any and all questions you have about the exhilarating, terrifying, and wonderful experience of dating and having sex with new people after becoming a parent. Send me your questions at

Rebecca Woolf writes Romper’s Sex & the Single Mom series. She has worked as a writer for more than two decades and is the author of two books, Rockabye: From Wild to Child and All of This: A Memoir of Death and Desire. You can subscribe to her newsletter, The Braid, for more. She lives in Los Angeles with her four children.

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