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On Thursday our Pleasure Fellow Ana Santos had the pleasure of interviewing Carolyn Lee Arnold, author of Fifty First Dates After Fifty on our Instagram platform. It was an amazing, sex-positive conversation which Carolyn now continues below with a fabulous, honest, eye-opening discussion of her dating project, pleasure, safe sex and the Pleasure Principles. Sit, back, relax and read all about a world of sex we never really get the pleasure of hearing about.

The Pleasure Project is dedicated to ensuring sexual health, sexual rights, and sexual pleasure throughout one’s lifetime, backed by their seven Pleasure Principles that include Love Yourself.  The sex-positive, pleasure-based approach to sexual health that The Pleasure Project promotes is crucial to counteract the negative and misleading messages about sex that are taught in our schools and shown in mass media.   

What a herculean task—to change the world’s attitudes and practices about sex! When so many forces are aligned against that change, it helps to be inspired by a vision of what sexual health, sexual rights, and sexual pleasure could look like for an individual if those changes came about.  For a real-life vision for a mid-life woman, I offer my recently-published book, Fifty First Dates After Fifty: A Memoir. The goals of The Pleasure Project are embodied in my dating story, which is described as an “upbeat memoir about the search for a partner in midlife…[and] a celebration of a woman’s unabashed sexuality.”

Picture from @carolyn.lee.arnold Instagram

I was 58 years old when I challenged myself to find my life partner by going on fifty first dates. Touch and sex had always been vital for me. Since my early 20s, I had been frequently sleeping with and/or enjoying sex with someone, whether or not I had a partner, as I went through a series of short relationships with men, then women, and then men again. So, when I embarked on the ‘dating project’ that is the subject of my book, I planned to continue being sexual, even though I was looking for a committed long-term monogamous partner. I figured that dating was not the time to be monogamous. What helped was that I had been through ten years of workshops on love, intimacy, and sexuality, which reinforced my own instincts to celebrate pleasurable sexuality with consent and good health.


The Pleasure Project’s dedication to sexual rights and sexual health and sexual pleasure forms the basis of a sex-positive life, and those tenets provided the foundation for my sex-positive life. 

SEXUAL RIGHTS.  Enjoying sex was only possible because I knew that I had a right to say no or yes to sex at any time. It was knowing in my bones that I could say no, that led to my most enthusiastic yes’s. I learned through experiential workshops that it was fine to say no, yes, or change my mind about what I was doing at any point in the dating process, from deciding where to go to dinner to deciding whether to have sex, to changing what I wanted to do sexually right in the middle of it. This is a basic Sexual Right. For the first date of my dating project, I shared a naked sauna with the guy. Afterwards, I was happy to sit on the couch in our robes, kissing and stroking his face.  But he wanted to make love and said he could not stop if we kept kissing. So, I said I was sorry I was not ready for that, and got dressed and left.  I assumed he would respect my choice, and he did, because I was so clear. 

SEXUAL HEALTH. Comfort with sex and being able to ask for what one wants naturally leads to being able to ask for and insist on safer sex. In the workshops, we practiced discussing our ‘safe sex’ practices as if we were about to have sex with each person (we weren’t). I got so used to it that it seemed natural to bring it up as a sexy part of foreplay.  In one late-night scene, when my date and I were about to be sexual with another couple, we all went through our sexual histories, tests, and preferences in a long, engaging conversation. By the time we finished, we were too tired to do anything, so we just went to sleep for a few hours.  However, when we woke up, we knew what each person required to feel safe.

SELF LOVE and SEXUAL PLEASURE. It’s much easier to accept sexual pleasure when we love ourselves. But how do we learn to love ourselves?  There are many support resources to help us learn—positive friends, therapists, support groups, and personal growth workshops, both local in-person and online.  It’s also an inside job—each of us needs to practice loving ourselves every day to reinforce that self-love and know that we deserve sexual pleasure.

If we cultivate self-love, believe in our sexual rights, create a safe sexual container, and seek out sacred sexual experiences, we can experience sexual pleasure and a sex-positive life.

The below vignettes from my memoir illustrate the Pleasure Project’s sex-positive vision of sex as self-loving, pleasurable, healthy and sacred, even as we age: 



Early in my dating project, I was still feeling grief at breaking up with my former boyfriend Peter, and not feeling very sexual.  I went to the beach to cry out my sadness.

Watching the waves and birds, I got ready to cry and shout to myself in sorrow about Peter. But I found myself longing for a gorgeous dark-haired guy who was meditating farther back on the shore. I’d passed him during my walk along the beach.

Hmmm, I thought, I’m feeling turned on, wanting to touch and be touched. I thought I missed Peter. But what I really want is that stranger to make love to me.

Another wave rolled in. I got up and shouted out loud, “I’m feeling fine here by myself! I’m going to be fine!” I stomped on the sand and opened my arms to embrace the ocean in the late autumn sun. What had started as a yearning in my groin for the stranger became a rush of energy pulsating through my torso and heart and out through my head and limbs. My whole body was vibrating, and my chest felt open and light. I felt solidly on the sand yet also expanded over the waves into the vast sky and sea. Waves kept coming in, adding the energy of the ocean to mine.

During four years of commuting to Hawaii to see Peter, I had shut down my sexual feelings except when I was with him, and even then, menopause had diminished my lust. I had feared that feeling sexual was behind me, but now those feelings, the key to my own vitality, were rushing back.

Peter was gone. I was trying to feel sad but instead felt excited. I laughed out loud. Soon I would start dating and being lovers with other men. I was celebrating my new freedom. Would it lead to a partner? I didn’t know, but my friends, potential lovers, the dates to come, and these feelings in my body would sustain me on this journey.


My lust returned with a few of my early dates, and some of these men became my ongoing lovers. With them, I played out pleasurable fantasies such as this one.

I found a long unlit stretch of road with a wide shoulder up against dark vineyards and parked my car. He pulled up behind me, and we met outside between his car and the fields. I reached up to kiss him. He reached down and pulled out his cock.  My shock turned quickly to longing—my belly trembled; my yoni moistened.

“Hmmm,” I said in a low voice. “If you have a condom for that, I’ll suck it.”

He did and I did, kneeling down on my jeans in the gravel behind his car. Looking up at him under a wide expanse of starlit sky, I sucked his cock in and out of my mouth, the gravel digging into my knees. My submissive position, the location on the side of the road in the dark, my mouth full of this almost stranger’s cock, and the slight pain in my knees were all deeply arousing. I had wanted this—pure sex. The stars twinkled in approval.


While I celebrated the return of my lusty sexuality and had many encounters that consisted of pure delight in each other’s bodies, I also held onto my view that our sexuality is sacred.  I refer to my vulva as my ‘yoni,’ a Sanskrit word that has the connotation of sacred space, and I’d met my man of roadside sex at a tantra workshop, which promoted encounters of the more reverent type.  All of my workshops on love, intimacy, and had begun with ceremonies of eye-gazing with each person in the room, listening to each other pour out our hearts, and reverently stroking each other’s face as a way to be present and honour each person – the basic prerequisite of deep, soulful sex.

“And now,” the male facilitator said gently from the front of the room, “one of you, take your hands and cup your buddy’s face, look into their eyes, and see if you have permission to gently stroke their face.” Peaceful music enhanced the tenderness of the moment. Andrew asked if he could go first, and as I nodded yes, he held my face and smiled into my eyes. As his fingers started stroking my face, my heart melted. His touch was delicate and sure. I realized I’d never been touched so reverently, even in sexual situations, and the facilitators had made it clear that we were not going to be sexual. Again, I felt filled with peace. I had come home. My face relaxed, and more tears flowed.

 When it was time to switch roles, I tentatively brushed my fingers over Andrew’s little round face, and he started looking beautiful to me, this funny-looking man with such a kind heart.

Carolyn with her book (@carolyn.lee.arnold)

How did my sexy dating project end?  I’m living a sex-positive life and loving it! I found the perfect partner–someone who loves touch and sex as much as I do and also wants to stay connected emotionally. My lust has diminished, but our emotional and sacred connection makes us want to connect and pleasure each other. Even if I don’t feel sexual, I can get interested by becoming present with my partner, quieting my mind, and tuning into my body. I give him pleasure by touching him how he likes, and he knows the special types of touch that turn me on, so I start feeling that longing, and we proceed towards my orgasm, which leads to my giving him more pleasure that we both share.