Affairs, Desire, and Choosing Herself: A Conversation with Rebecca Woolf

On longing, risk, and the kind of intimacy worth having.

Dec 23, 2025

Welcome to Lust in Translation, a newsletter exploring what ignites your pleasure, confidence, and desire—by yours truly, sexologist Natassia Miller. If you’re new here, now’s a great time to subscribe.

Rebecca Woolf by photographer Jacob Boll

Long before becoming a sexologist, conversation was my first fieldwork. I was the one at dinner who somehow got everyone talking about sex, desire, and the quiet negotiations happening in their relationships.

I’ve been fascinated by how layered our erotic lives are for as long as I can remember.

When I read All of This, Rebecca Woolf’s memoir about marriage, motherhood, infidelity, and death, I was instantly hooked. Raw stories like hers are usually shared behind closed doors, not published for strangers.

Few people are willing to write from that much truth.

As Esther Perel reminds us, “If we were fantasizing on a bed of roses, we wouldn’t be having such interesting talks about this.” It’s in the mess—the ambivalence, the betrayal, the desire that refuses to die—that we recognize ourselves and feel less alone.

So of course, I had to interview Rebecca Woolf.

Rebecca is one of my favorite writers, first contributing to the Chicken Soup for the Teenage Soul series in the 1990s and later publishing her personal blog Girl’s Gone Child, which chronicled early motherhood, marriage, and family life in Los Angeles. Besides her book All of This, she hosted a limited podcast series called No Shame (I binged it) and writes the braid–one of my favorite Substacks.

Without further ado, our interview.

Natassia: Let’s start at the beginning. You were raised in suburban San Diego in the 80s and 90s. What were the key messages you received about sex and sexuality?

Rebecca: I grew up in Encinitas, which was basically ground zero for surf and skate culture. Kelly Slater, Rob Machado, Tony Hawk—those were the guys being propped up as the cultural leads, and the way you had power as a girl was by orbiting boys. So, my entire adolescence was as a groupie who was there to prop them up or give them emotional or sexual support whenever they needed.

I got a job at a local skate shop and learned how to set up a skateboard, but was not allowed to ride one.

I remember my parents got me a skateboard when I was maybe 10 or 11. I lived on this cul-de-sac full of boys and they took my skateboard, broke it in front of me and said, “You can’t ride this,” and me internalizing, “Okay, I guess my role is to sit on the curb, cheer you on, and be sexually available when you want me.”

I learned that I could rise in the ranks by being the “best pro-ho,” the cool girl who set up their skateboards, slept with them, and didn’t ask for anything.

Natassia: How did your parents talk to you about sex?

Rebecca: My mom was super sex-positive. In my early teens, she offered to get me a vibrator. She knew that I was sexually active pretty early and never made me feel bad about it, never shamed me for anything I wore or anything I did.

The big script then—and I think still, for a lot of mothers and daughters—was, “Wait until you love someone before you have sex with them.” Which is, to me, the worst possible advice, because when you’re a teenage girl you fall in love with literally everybody.

So I’ve flipped the script with my kids. I tell them, “You’re ready to have sex when you’re sexually mature enough to advocate for your desire and for yourself.”

Natassia: I love that. I remember that you also gave your daughters vibrators and gave your son the book Becoming Cliterate.

Rebecca: It’s so funny, too, because I gave it to him thinking he’d be like, “Ugh, Mom” and he was like, “Oh, thanks.” And later he really thanked me for it.

I’ve always had age-appropriate sex positive books in the back pockets of our minivan, so anyone could take a gander. And we talked about it all the time.

My whole thing with consent, which I’ve been talking to my kids about since they were little, is you never put your pleasure after another person’s comfort. Not only in sexual situations, but in general.

Because I write about sex, I have boxes of vibrators in my closet of all shapes and sizes. So I gave all of my daughters vibrators, and initially they said, “Ew, gross, Mom.”

I told them they could use it, or not. They could put it away for later. I just wanted them to have access. Now, my older daughter is the one whose friends come to her asking if I can get them vibrators.

I’m honored to be the auntie who’s there for all the girls. They know that they can call me if they really need anything that has to do with their sexual health.

When I’m driving my daughter and her friends to parties, they know they can ask and have these conversations in confidence. It’s my favorite place to talk about sex with teenagers because you’re not sitting them down and making eye contact with them.

It’s a lot easier to talk casually about sex when you’re driving and everyone’s looking in the same direction and not at each other.

Natassia: My mom was also very open about sex. We had a line of communication where I felt safe asking her questions. She also taught me about consent. So, I am very thankful for that and I think it’s fantastic that you do the same for your kids.

Rebecca: I was actually just having this conversation. There’s this pink tax of raising teenage daughters and how different it is to put my daughter on public transportation than it was for my son.

I have been thinking so much about it, because she no longer takes the bus after this guy tried to assault her and then chase her.

I did not have to deal with this with my son. So now I spend four more hours in the car to get her to school and back, because I can’t put her on public transportation.

I’ve had to have these conversations with my girls, especially living in a city like LA, where I want them to be free, roam around and have a social life. But there’s this frustration about being in a world where it’s not enough to equip them with all the knowledge: understanding consent, advocating for their desires and being strong. Because they have to deal with people who don’t know these things.

I was weighing in on a question of splitting the bill on a date. Someone else said that if you want equality, you should split the bill. And I think absolutely not. You don’t get to split the bill until we close the pay gap and until my daughters can get on the bus and ride safely.

We’re risking our lives to meet you for a drink, the least you can do is pay for it.

Natassia: You’ve shared that some of your early sexual experiences were non-consensual. How did that shape your relationship to sex in your teens and early twenties?

Rebecca: I’ve always been an extremely sexual person. I learned to get myself off very young, so my sexuality did not come from a partner introducing me to my body; I already knew what felt good.

The problem was that my early partnered sexual experiences were non-consensual. So I swung hard in the other direction. I became the girl who pursued sex, who walked up to men and told them I wanted to sleep with them. It felt like reclaiming power.

My late teens and early twenties were me sleeping with everybody, basically. I went from being the girl who fell in love with everyone to being the girl who felt nothing during sex.

My emotional and sexual selves became totally separate. I got a lot of power from casual sex, but it was performative power. It wasn’t about my pleasure; it was about being “good in bed,” about how turned on they were.

I thought I was the one in control, but in retrospect I see that a lot of that was still about external validation, not internal satisfaction.

Natassia: You married Hal at 23 when you got pregnant, and you’ve written about non-consent showing up in that relationship too. How did your dynamic with him evolve, especially once you became a mother?

Rebecca: When we met, our relationship was super sexually charged.

I was still in that mode of wooing men by taking care of them—having sex with them, cooking for them, listening to them, asking them endless questions, not needing anything back.

I married the kind of guy I’d been fucking for ten years: someone who loved being loved by me, who was very comfortable being taken care of.

Then I had a baby and everything flipped.

I suddenly had an actual child, and I did not want to mother a grown man anymore. I didn’t want to serve men or center their desire. I wanted to be in my own body, in relationships where someone asked me questions, cared about me, wanted to take care of me because I was already taking care of someone else.

That was the beginning of the end of our marriage, even though we stayed together 13 more years.

Natassia: You’ve been incredibly honest about having affairs through most of the marriage. How do you understand that now?

Rebecca: I started cheating on him within the first year. It sounds wild, but those affairs were where I actually learned what I wanted sexually. I did not feel safe in my marriage advocating for my desire because our foundation was my service to him.

With lovers, there were no stakes. I could say what I wanted and not worry about hurting their feelings or making them angry.

I was scared of Hal from the beginning. I was drawn to men who scared me, who were dominant and powerful in that old groupie dynamic. That’s not who you want to be married to when you actually need reciprocity and care.

So I felt very justified in my affairs. I was able to escape a marriage that I did not feel safe in, learn what I wanted sexually and also recognize that monogamy never came naturally to me.

Natassia: What else did you learn from these affairs? What did they bring out in you?

Rebecca: It’s interesting because there was one that lasted the longest. It was mainly long distance because he lived in New York.

We saw each other sporadically, but it was for the most part really about longing because we would write each other these letters. There’s probably thousands of emails over the years because we would send each other emails back and forth and so much of it was writing about fantasies.

He’s a writer too and I realized that I had never had that kind of relationship or connection with someone who was also a writer. So we had this whole language and I think through that relationship I was able to articulate fantasies, desires, things with him that I’d never articulated before.

It was almost like we were prompting each other to dig deeper into this fantasy world with each other, which is the thing about affairs. It’s all fantasy, right? The majority of people you have an affair with, you’re not going to have a relationship with. They only work in the periphery of your life.

So I went searching into this part of my sexual psyche that I’d never had before. And because of that, we got really, really close sharing intimate fantasies.

My husband never would. It just wasn’t him. It wasn’t us. It opened me up to this whole other world which I knew I wanted to pursue. After he died, I did. I pursued it.

I wanted to have sex with women. I wanted to have threesomes. I wanted to have an open relationship where we were both having sex with other people and then talking about it, and then having sex with each other and talking about it.

And then there would be these times where he’d be having sex with me, and I’d be on the phone with some other girl he had sex with describing it to her.

We had this really fun, wild sex life that felt so safe with him. This is the first boyfriend who I wrote about in my book.

It was the same thing for him. He had never had a relationship like that either. He had just come out of a 20-year marriage. He’d only been with a handful of people.

I was able to be in a partnership with someone, not cheat on them, and be totally open about everything I was feeling for him and other people. So, it really was, and it still, by the way, to this day is the only relationship I’ve ever had where I felt like those two parts of myself were able to exist together.

It was super healing for me, especially post marriage. I will forever sing his praises and be so grateful to him for that.

Natassia: How does your sexuality feel now, in your mid-forties, compared to those early years?

Rebecca: I’m 44 and have always had an abnormally high sex drive. People keep saying, “Oh just wait, you’re going to reach a certain age…” [where your sex drive will decline] but I’m not there yet.

I feel way more sexually embodied the older I get. I feel fearless, super open.

In the past, I have mainly gravitated towards men 10 to 20 years older than me. I realized in the last few years that I need to start going in the other direction, because they can’t keep up. It’s not even necessarily an issue about getting hard. It’s a stamina thing.

They don’t want sex as much as I do. It makes me feel needy or desperate to ask for sex, you know what I mean?

I want to be in an equitable relationship with someone who’s at my level and I think, sexually, women in our 40s and men in their late 20s, early 30s are probably more aligned.

I have a lot of friends, a lot of women in their 40s and 50s and 60s, by the way, who are sleeping with men in their 20s and 30s. It’s hot. The power dynamics are interesting. Younger men are far more open to everything.

I realized maybe a couple years back that I’d never been with someone younger than me ever. Not even my own age. And what was it about that power dynamic that was attractive to me and what did that mean actually?

A lot of it came from feeling like I wanted someone to overpower me.

And what I’ve learned about myself in the last few years is that it’s actually fun to play with that power dynamic of being the older woman and having more experience. What does that look like? What does that feel like?

Especially because I write about this, I want to understand not only my own sexuality, but also the spectrum of sexualities.

If you want to dive deeper into Rebecca’s journey, I highly recommend reading All of This and subscribing to her substack the braid.

And if you know someone who’d enjoy this conversation, please pass it along.

Discussion about this post

Ready for more?