Fifty First Dates After Fifty: A Memoir

Prologue

MONOGAMOUS DATING

You’re still sleeping with other guys?

George asked this in a voice shrill enough for the other diners in the cozy Ethiopian restaurant to hear. Several looked over at us—a middle-aged white couple—with expressions ranging from annoyance to amusement.

I had suggested this romantic Berkeley spot for our fifth date because I thought that George, who performed with an African dance troupe, would like Ethiopian food. It was a bad place to have this discussion.

But I told you that on our third date, I whispered in a low voice, trying to discourage eavesdropping by diners who were still looking our way. Before we slept together.

You said you had other lovers then, he said. But why would you keep seeing them?

’Cause they’re my lovers, I said. They support me while I look for a partner.

George leaned back in his chair and shook his head in disgust. Wispy strands of long brown hair had come loose from his ponytail and swayed on either side of his thin face.

How could you do that to me? he asked with sorrowful brown eyes.

Inside, I was sighing. I didn’t want to hurt him. George had his own, traditional dating rules, and I had violated the one that said stop sleeping with all other men after you spend a night with me. It was monogamous dating. And while I eventually wanted a monogamous partner, I was not interested in committing to one man while I was still dating.

I wondered how much time and how many apologies I owed this sweet man before I gently extricated myself from what he thought had become a relationship. My experiment of dating men who were outside of my usual circle was not going well. Could I only relate to men who, like me, had attended personal growth workshops on relationships?

I was fifty-eight years old, and I had a goal of finding my life partner by going on dates with fifty men. George was date number 31. I’d started the project with great optimism, but now that it was more than halfway done, I wondered if I would find a partner of any type by the fiftieth date.

It had been over a year since I’d said good-bye to Peter, and I was determined to go on, no matter how long it took. Date 32 was scheduled for Saturday—a walk around the Berkeley Marina. This guy looked promising . . . a fifty-six-year-old therapist from Marin County.

PART I

LETTING GO

LETTING GO ONE (2008)

Peter, I love you, I honor your journey, I set you free.

I gazed into Peter’s blue eyes, twins to my own blue irises. Even in the low candlelight in my living room, his eyes twinkled over his tan cheeks; his wild white hair still looked like a blond halo to me. Peter and I had been together for seven years—five years longer than the two he had said he was good for and five years longer than my longest relationship. Tears pressed into my eyes as I imagined letting go of this man, who I still believed was the best partner for me.

Carolyn, I love you, I honor your journey, I set you free, Peter said kindly, but free of tears. I believed that he loved me—but not enough to stay with me. He was ready for seven months of traveling in Europe and India, ready to be single again.

How could I let go of someone who had been my perfect match for seven years? Peter was a happy Buddhist beach boy in his late fifties, living a mellow retired life in Hawaii. His upbeat attitude and peaceful home had provided an oasis for me, a new age California girl in her late fifties living a hectic professional life in the Bay Area. Good friends for a year before becoming lovers, we could talk about anything and end up laughing. He would say, Great! and mean it, after anything I said. He bought me gifts—an iPod Nano to have music when I ran, a snorkel and fins for my visits to Hawaii, pillows when mine had lost their fluff, and clitoral cream to help me have better orgasms. How could I let go of someone who bought me clitoral cream? Even though I was making plans to date other men, it was hard to imagine being with anyone other than Peter. I would need more than a letting-go ceremony for that. Luckily, I had a plan.

THE PLAN

I’d come up with the idea a month before Peter left for Europe. My friend Kate and I were sitting on the grass beside the crowded Oakland Grand Lake Farmer’s Market on a sunny September Saturday, catching up while we took a break from buying flowers and organic vegetables. Kate was in my women’s group, and we loved talking about relationships. Younger than me by fourteen years, she was transitioning from a career as a pole-dance teacher to a therapist and was not afraid of asking direct questions.

Are you looking forward to dating when Peter leaves? Kate asked.

Kind of, I said. But I’m going to miss Peter a lot. I sighed. I’ll probably look for someone just like him!

You were getting pretty bored with him, though, remember?

She was right. My latest trips to see him on the Big Island had left me feeling more restless than relaxed.

But my heart still loves him, I whined, and believes we’re the ideal match. I watched a happy young couple float gracefully through the market like a pair of swans.

"He was ideal for you all those years, but now someone else might be better," said Kate. She perused the crowd, as if the better guy might be in sight. I had confessed in our women’s group that I was starting to want a real partner, not a part-time temporary one—someone who would do what Peter could not: live nearby, do something besides relax, and commit to a long-term relationship. But they would have to be as joyful and loving as Peter—a Peter-plus person.

Maybe I need to go on a lot of dates to find someone, I said, following Kate’s gaze to a gangly man walking by. It might help me get over Peter and see what other types of men are out there.

That’s not a bad idea, Kate said, turning back to me. How many dates do you think it would take?

There was that movie, I said, laughing. "Fifty First Dates."

Didn’t she go on fifty first dates with the same man . . . because she had amnesia?

Yeah, I said, "But I could go on fifty first dates with fifty different men."

That’s a lot of dates! She looked at me with an admiring smile.

I liked the sound of fifty. When I bought my home, I’d looked at over a hundred houses until I found the perfect one. As a statistician, I knew that samples of only fifty were needed for significant results. Fifty dates sounded like plenty to get over Peter and check out different types.

Maybe I could make a research project out of it, I said. My heart beat faster. That was it! I worked as a researcher at a college. I gathered data on the students and determined which groups needed support. By dating a lot of men, I could determine if there was a better man for me than Peter. The whole idea cheered me up. It wasn’t just dating—it was a dating research project!

I think I’m going to do that, I said. I’ll set a goal of going out on fifty first dates.

Sounds like a great plan, said Kate. And you know a ton of men.

Kate and I had both attended workshops put on by the Human Awareness Institute (HAI), a Bay Area nonprofit that offers classes on love, intimacy, and sexuality.¹ In my ten years of participating in and then volunteering to assist with HAI workshops, I had met hundreds of people seeking better relationships. Many of my fellow volunteers were single men, and some had told me, with a twinkle in their eye, Carolyn, if you’re ever available again, let me know. What better group of men to date than those plucked from the HAI pool?

Yeah, I’ll start with men from HAI. But there are other places I can go to meet men, like Sierra Singles hikes, or the meditation nights for singles at Spirit Rock. Also professional singles events and online dating sites. And I don’t have to limit myself to men who’d make ideal partners—I can explore different types of men! I was getting excited.

I can’t wait to hear how this goes, Kate said, smiling in amusement.

But then I felt a pang of doubt. What if I don’t find anyone better than Peter?

I doubt that’ll happen, Kate said, looking more serious. It’s natural to think that the last guy you were with was the best—especially since he was your first long relationship. But you’re breaking up for a reason. After you start dating, I don’t see you being able to go back.

I pondered her words silently as I watched a tall, suntanned man in blue nylon running shorts walk by carrying a mesh bag of oranges. He looked about my age—and definitely a type I wanted to explore.

Kate caught me staring and grinned, and I grinned back.

I hoped she was right.

FLASHBACK

The Human Awareness Institute had prepared me well for this project. I had turned to HAI in my forties, when I became serious about finding a life partner and realized that my dating choices had led only to short-term relationships. After twenty years working through a progression of jobs and graduate school degrees in women’s studies, statistics, and education, I had finally settled into a community college research job that I loved. Now I had time for a personal life, but I was afraid I would never find a lasting partnership if I didn’t change what I was doing. So I was relieved to learn that HAI (pronounced Hi) offered weekend workshops on love, intimacy, and sexuality just two hours north of my house, on the grounds of Harbin Hot Springs, a new age retreat center that I frequented often.

It was natural for me to turn to nontraditional personal growth workshops to learn how to improve my relationships. I had never wanted a traditional life, despite being primed for it by my middle-class upbringing in the Los Angeles suburbs of the early 1960s. My conservative parents, who were transplanted New Englanders, thought they were raising me to be an educated housewife like my mother, and had similar conventional ideas for my younger brother and sister.

When I was fifteen, they sent me to a girls’ boarding school back East, far from the permissive California of the ’60s. Flying back and forth across the country, however, planted seeds of independence. And by the time I started college, the ’60s had reached the East Coast. As a student at a women’s college in Massachusetts in the early 1970s, I tried marijuana, protested the Vietnam War, and abandoned my parents’ conservative views for more liberal ones. I also woke up to feminism. My father had not let my mother work until their youngest was in grade school, and she’d resented it. I vowed to never become economically dependent on a man. My parents’ traditional suburban life looked boring to me—I wanted my life to be a grand adventure.

After college, I moved back to the West Coast, where I settled in Berkeley and spent the next twenty-five years exploring alternative lifestyles. I moved into a vegetarian cooperative house, waitressed, and volunteered at the Berkeley Free Clinic, which offered free health services to demonstrate that health care was for people, not profits. I went to spiritual ceremonies, tried LSD, and started backpacking by myself.

While working in a feminist women’s clinic, where we demonstrated women’s control of our own bodies, I lost interest in men, who seemed stuck in outdated gender roles, and declared myself a lesbian. For eighteen years I thrived on being at the forefront of social change. I moved into an all-women’s house and embraced all the emblems of a lesbian feminist in the 1970s—wearing overalls, cutting my long blond hair short, going to women’s music concerts and festivals with lovers, and leading women’s backpacking trips. We were redefining what it meant to be women.

Identifying as a lesbian enabled me to separate financially and emotionally from men—I earned two master’s degrees and a PhD during this time and loved many women—but I never found the partner I dreamed of. In 1993, when men were emerging from first marriages, therapy, and men’s groups with a feminist awareness, I grew interested in them again.

Dating men in my forties after an eighteen-year hiatus was like being a teenager without the restrictions. My lesbian years had given me a healthy self-confidence, and I knew I didn’t need a man for financial security. I was attracted to their bodies and wanted to try out all kinds of male-female sex. My feminine side came out, and I started wearing dresses and heels again. After experiencing the full range of personalities among lesbians, I could see men as the complex people they were, trying to relate to women as best they could. I was still not interested in getting married—it felt too close to the housewife role—but I did want a long-term equal partner.

But five years later, I was still alone. So turning to an organization like HAI—which had a nontraditional approach to relationships, welcomed people of all sexual preferences, and held their workshops at a new age retreat center that reflected my own alternative lifestyle—seemed completely normal.

THE WORKSHOPS

When I arrived at the spacious, high-ceilinged wood-and-stone conference center for my first HAI weekend retreat in 1998, I could see that the workshops would be the perfect training for me. I was ready to learn how to have a successful relationship, and that is exactly what these workshops taught. HAI’s philosophy about relationships was that loving others started with loving yourself. One-on-one and small-group exercises promised to give me and the sixty other people there, half women and half men, the experience of loving ourselves and appreciating others.

My first workshop started right off with learning to look for the goodness in each person and was led by two facilitators, a man and a woman. Find a partner and form a big circle, said the male facilitator. In this ceremony you’ll get to greet everyone.

As I wondered whom to ask, a tall, thin man moved closer and said, Would you be my partner?

Sure, I said, relieved, and we moved into the circle.

Now face your partner and put your hand on your heart. Angelic, harmonious music played softly over the speakers. The female leader said, Gaze into the eyes of this person, and say with your eyes, ‘I’m glad you’re here.’ I gazed up into the man’s eyes, saw the gladness coming from him, and sent my own gladness back. I felt a surge of joy. After a few seconds, she said, Open your heart, kiss the hand, and step to the left. I followed the gesture they had taught us—I took my hand off my heart, opened it as if for a hug, and then took the man’s hand and kissed the back of it while gazing into his eyes before I moved on, feeling tender toward him. My next partner was a plump woman my height who smiled serenely at me. With this partner, the leader said, look into their eyes and silently send the message, ‘I accept you just as you are.’ We both beamed. I felt a deep peacefulness, like a coming home. We carried out the same heart and hand gesture, a gentle leaving. This ceremony was just what I had been looking for—a way to connect with men and women closely, without having to think of what to say—just experiencing and appreciating each person. We rotated around the circle until we had been with each person there. The facilitators’ caring words helped us focus kindly on each one. There were so many different types—in height, size, age, skin tone, gender—and they each communicated differently with their eyes. Some could not look me in the eye for the whole time, but others had sparkling eyes that looked eager for connection. I wondered if that meant they liked me. I tried to project acceptance to each person.

Later that evening, we got to pick a buddy for the weekend. They said that we would do a few exercises with them, but mainly this would be our support person. When we were asked to select a buddy, I looked around at the sixty people and froze. Do I pick a woman I feel safe with, or a man I’m attracted to? Everyone was being picked, and a short, balding, smiling, Buddha-like guy was looking at me with a goofy grin.

Would you like to be buddies? he said. My name’s Andrew.

I wasn’t attracted to him, but I didn’t see any other options. Sure, I said, feeling skeptical that we could relate to each other.

But when Andrew said he was a chiropractor who led fire walks—where people walk over hot coals to overcome their fears—and that he’d come from Santa Cruz with his men’s group, I realized he was from a similar alternative, feminist background. Soon I would learn that most people who came to HAI were seekers of some sort. Although not everyone walked on hot coals, all were looking for new ways to find love, self-acceptance, and life purpose. Ranging in age from twenty to eighty years old, with economic situations from low income to very prosperous, most were, like me, middle-aged and middle income. For everyone, personal growth was a high priority.

In our first paired exercise, Andrew and I sat against backrests on the floor facing each other, talking about our past relationships and why we came to the workshop.

I’ve been wanting a male partner for a long time, I said, feeling my tears begin. I’m forty-seven, and I’ve never had a relationship last for more than two years. Andrew nodded, following the instructions to just listen rather than respond and try to fix me. I sank into my own sadness, and my tears flowed down my cheeks. I felt Andrew’s kindness and compassion in the way he listened so fully to me, nodding with empathy.

When it was his turn, Andrew said, Well, my men’s group thought this would be a good experience. I’ve been divorced for a year, have joint custody of two young kids, and things are good. I’m not necessarily looking for a relationship, but I’m open. I nodded, smiling at him.

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.

Andrew turned out to be the perfect buddy for me. The next morning, I was cursing myself for not getting up early enough to go running before breakfast. Don’t you see what you’re doing to yourself? he said to me. You can’t love yourself when you keep seeing yourself as wrong. Hey, you needed the sleep.

But it’s too late to go running! I wailed.

No, it’s not. Let’s go.

While we ran along the sun-dappled canyon road, surrounded by tall pines covering the steep grassy hillsides and leafy branches waving over us, Andrew taught me to laugh out loud in gratitude for the beauty of the California hills. I felt a glimmer of enjoyment in the moment and loved myself a little bit more. Andrew would be a friend for years to come.

Besides a buddy, we also chose a small group for the weekend to be our support team. My small-group leader was Bruce, a HAI volunteer. I’m fierce at loving myself, he said in our first meeting. And because of that, I finally found my wife—my life partner—and I’m staying in love with her. Even though she loves me, I still tell myself how much I love and appreciate myself every day. I hoped to get to that loving place with myself and a partner.

As our group of four sat in a circle on the floor, Bruce asked us to notice any negative thoughts we had about ourselves and share them. I had plenty of negative thoughts about myself, many of them from my mother. As her firstborn, my teenage rebellion had challenged her, and she had criticized me harshly—for my hairstyle, my clothes, my interest in sexuality, and the liberal attitudes I’d picked up back East. Because I left home at age fifteen, we never got to resolve our differences, and her disapproval continued whenever I visited her. Although she told me often that she loved me and was proud of my achievements, her critical voice had settled into my head. When it was my turn, I started listing my faults, echoing my mother’s words.

I’m so critical, I said. I notice what people, including myself, are doing wrong, and I focus on that. I try not to say anything to others, but I often curse myself out loud for what I do. I could barely look at the other group members, but I felt them looking at me sympathetically, so I went on. Also, I’m selfish, I said. I think I’ve taken this whole taking-care-of-myself thing too far. I put myself first in most situations. I felt a flush of shame at even admitting that. I also worry a lot—about everything. It’s part of focusing on what could go wrong rather than what could go right. I was feeling worse and worse, but I glimpsed some of the group nodding as if they understood. Then I remembered why I was there. I’m afraid that I’m not lovable—that because I’m critical and selfish and worry so much, no one will want to stay with me and be my partner. Lost in my tears, I slowly looked up at the group.

They were smiling at me warmly. Send this person some love and appreciation for what they shared, Bruce said. My little group sent me love with their eyes or bowed with their hands together. I still felt glum, but I sensed their support. Then we went on to the next person. By the time everyone had shared, we were all slumped in our seats.

Now, said Bruce, shake out your body, sit up straight like you are proud, and share what you love about yourself. Oh, good, I thought, this will be easier. My parents had given me positive messages as well. Their investment in my education had made me believe in myself. My mother had encouraged me to love my small breasts and wide hips. My father had always supported me in nontraditional pursuits. He’d bought me a toolkit to fix my bike and VW Bug.

I love my high energy, I started, which I got from my parents. It makes everything possible. I love that I found a career I love that supports me, and I’m proud that I was able to buy my own house. I hoped this didn’t sound like I was bragging. I had never imagined I could buy a house in the Bay Area as a single woman, but I’d