Scarlett.
A conversation with a "chronic oversharer" and “Marin County MILF” who enjoys getting spanked and San Francisco sex parties. And yes, her mum knows all about it.
Earlier this week, I had a 90-minute-long conversation with Scarlett*, a 48-year-old tech executive with whom I was connected by a mutual friend, Elliot. Elliot thought I should talk to Scarlett because, like me, she went a little bananas after signing up for a hookup app following her divorce from a man she wasn’t fucking. He also thought I should chat with her because she’s open, and honest, and funny, and has a load of provocative stories to share. He was right on all counts.
What follows is a condensed and edited version of our conversation.
*Not her real name.
NAOMI: Let’s dive in. I hear that you considered writing about your experiences at one point.
SCARLETT: The reason Elliot gave me the moniker “Marin MILF” is because I kept saying I had a really strong urge to tell people about my experience, and I couldn't quite figure it out because, as you would imagine, I'm terrified of my son somehow finding about it. And so I never quite got it off the ground, but I did start to take some notes and at least write down people's names and things so that it would be easier if I ever came back to it.
NAOMI: There’s so much to talk about.
SCARLETT: I'm a chronic oversharer, and I love to chat about it. But my girlfriends are just like, “I really don't want to know.” I'll try and tell them about stuff. And they're just like, “No, no thanks. I've had enough detail.”
NAOMI: So what was the impetus for you getting on sex and dating apps?
SCARLETT: It was July of 2022 and I had gone on a family vacation to Italy with the kids and my ex and my mom, and I found out that that my husband was having an affair. We'd already been talking about getting divorced, so it was not that sort of shocker, but I found out he was deeply involved with someone else. So we separated and my mom, being very lovely, was like, “What do you most want in the whole world right now? I'll help you.” And so I was like, “Can you take the kids?” And I went to stay with my best friend who lives in England. She is very open-minded about sex and she was like, “Scarlett, I think it would do you a world of good to get on a dating app just to see that men still fancy you and that you're still attractive.” I had put on a lot of weight at the end of my marriage, mainly driven by unhappiness. So I'd lost some confidence. And so my friend was like, “I've read this article in the New Yorker about this dating app and I think it's right up your alley.” And it was Feeld.
NAOMI: Were you at all scandalized?
SCARLETT: I’d had non-vanilla sex before. My first husband and I had a foursome and a fivesome. So I obviously had a predilection for group sex and whatever, but my long-term husband and I were together for 20 something years and married for 17 and he was not into any of that. In fact, he made me throw out all my sex toys when we got together; he felt like it was unromantic to have toys involved.
I once convinced him to come to a sex club with me and he really hated it. We left after 10 minutes. Once he booked a prostitute to have sex with both of us but then I got really stoned and freaked out and didn’t let her in, which I still feel bad about to this day. She was banging on the door being like, “I've come a long way, give me the cab fare.” And I was like, “I can't open the door!”