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He Might Have Been the One: Hope and Hurt on the Dating Scene

On a quest to find a new man, Carolyn Lee Arnold challenged herself to go on 50 first dates. She expected ups and downs, but never this.

Excerpted from Fifty First Dates after Fifty: A Memoir by Carolyn Lee Arnold published by She Writes Press.


“Would you like to come to my house for dinner?” asked Dale.

If he’d been a random Match.com guy, this invitation would have been much too forward. But we had several friends in common, and this adorable guy with a soft, open face and an early Beatles haircut had lit up the lights in my head. In his late fifties like me, he was a therapist involved with Burning Man, men’s groups, relationship workshops, meditation retreats, even community service projects—all part of the alternative culture I breathed. The invitation for a Monday night dinner in his home felt sincere and safe.

Dale would be date number 28 of 50 dates I had challenged myself to go on in order to find a committed partner.

Earlier in the call, Dale had told me he lived on a hill in the wine country, in a cottage with a hot tub and balcony that overlooked the vineyards.

“I would make a fire,” he said. “It would be quite cozy.”

“That sounds wonderful,” I said, attracted to the intimacy of the setting, and to him.

I had second thoughts about meeting Dale at his home as soon as we hung up. The drive would take over an hour from my house, and it was a work night. How would I drive home after the wine and hot tub we both said we liked? The obvious solution would be for me to sleep over. But that seemed too much, too soon. I was worried that because I didn’t really know him, I could get hurt.

What was I thinking? I wondered. What was he?

Read More: Suddenly Single… Now What? Tales and Advice From the Online Dating Trenches

Dating After 50: My Quest

Dale would be date number 28 of 50 dates I had challenged myself to go on in order to find a committed partner. It had been over a year since I started this quest, and by now I was ready to meet a man who matched me. During that first year, I’d dated a variety of guys who were not necessarily partner material, just to shake off my longing for my previous boyfriend, a loving but non-committal Buddhist beach boy. Now I was more focused on finding a partner and was alert to eligible men. And by now, I thought I knew I how to protect my heart.

The next day I called him back and said that I’d be more comfortable if we met first so we could see if we wanted to spend a whole evening together. I suggested meeting at the Berkeley Marina on Saturday for a walk along the bay.

“OK, I understand,” he said. “I hope I pass the test.”

My heart beat faster in a surge of hope and excitement—here was a man who wanted the same thing.

“I hope you do too!”

When Dale had first written to me, melodic chimes had gone off in the Partner Alert! area of my brain. I hadn’t gotten many responses to my profile, and here was someone my age who had a profession, had probably done a lot of work on himself, and knew some of my favorite people. I was hopeful. It felt like we were meant to meet. The online matchmaker was actually working.

“When was the last time you were in a relationship?” he had asked in that first phone call.

“I broke up with my last boyfriend a year ago,” I said. “We were together seven years, and we’re still good friends. I’ve been dating ever since, looking for my next partner.”

“What are you looking for in a partner?” he said.

I liked that he was conversant and comfortable with relationship topics. I should have expected that from a therapist. Phone conversations with online dates tended to be interviews, but they often circled around the important topics. He was getting right to the point of our ads—we had each declared we were looking for a partner.

“I want to be with someone who matches me on many levels,” I said. “A balance of closeness and independence is really important. How about you?”

“I’ve been in several long-term relationships,” he said. “I lived with my last partner for eight years. That was about five years ago, and we’re still friends too. I love being in relationship, but I’m very careful about who I choose to be close to.”

“So what are you looking for?” I said.

“Someone I can deeply share my life with,” he said, “although I’m also very independent. I’m looking for emotional, spiritual, and physical closeness without necessarily needing to live together or even spend all our extra time together.”

I had said those exact words to other dates. In a dating ad a decade ago I had asked for “a committed but not daily relationship.” My heart beat faster in a surge of hope and excitement—here was a man who wanted the same thing.

The Pre-Date

Saturday was a warm, sunny December day, with clear skies above a sparkling bay. I got to the parking circle early and waited on a bench. Several tall men emerged from cars, and I studied each one hopefully. I wanted so much to be attracted to Dale, since I was drawn to everything else about him. Finally, a tall, somewhat rounded, young-looking guy appeared; he met my eyes and smiled. I realized that he looked young because his face was plump with a dimpled smile. The rest of Dale’s body was large, not exactly fat, but substantial without any tone. It was not what I’d imagined from his picture, and I was not immediately attracted.

However, as we walked the path, we quickly fell into an easy conversation. He shared his feelings—“I’m a little nervous about meeting you.” He told funny stories—“So our whole Burning Man camp ran out of water, and we had to go begging from other camps!” He asked me deep questions—“What parts of you does your job satisfy?”—and really listened. I felt relaxed, interesting to him, and more and more interested in him. As we walked along, breathing in the fresh salty air, we touched each other’s arms—not too much, but enough for me to feel a physical connection.

He suggested that we stop and gaze into each other’s eyes—my favorite way to connect. We sat on a bench, facing sideways toward each other. His eyes were kind and exuded deep calmness and acceptance. Although I was not becoming more physically attracted, my heart was responding. I was feeling really good, and congratulated myself on proposing this “pre-date.” Now I was willing to take the risk of ending up an hour away late on a work night.

The Dark Night

The next evening, Sunday, I was holding my annual winter solstice gathering at home. Each year, I offered this ceremony for my close friends to honor the darkness of the longest night of the year and celebrate the return of the light. Sitting around the fire, we would declare to each other what we wanted to let go of into the darkness, and what we wanted to bring into the light.

I let the waves wash over me—waves of tears, waves of lost hope.

In a gesture of inclusiveness and hope, I had invited Dale to the gathering, but he was busy. I was feeling excited about getting to know him. During the part of the ceremony when we declare what we want to “bring into the light,” I would be declaring that I wanted to bring in a new partner, and thinking that it might be him.

About an hour before my guests arrived, Dale called.

“You must be busy getting ready for the solstice,” he said. “But I wanted to tell you something. Do you have a minute?”

“Sure.” He was right. I was in my usual last-minute rush of food and fire preparations.

“I’d like to cancel our date tomorrow. I’ve been thinking about it, and I just don’t feel we’re a match.”

“Really? Are you sure?” I was thinking, What???! That pre-date was for me not you!

“Yeah,” he said. “I’m sure. I wanted to let you know before your solstice gathering so you could get support from your friends.”

Right, a therapist would think of my support needs, I thought, tumbling into hurt.

“Thanks,” I managed to say. “But I’m disappointed. I was looking forward to getting to know you.” I was thinking, How could he know? I wasn’t sure, but I was willing to risk another date.

So I said it. “How could you know?” The rejection was sinking in.

“I just do,” he said. “I trust myself a lot.”

How could I argue with that? “OK. Thanks for letting me know.”  

“You’re welcome. Best wishes on finding a partner.”

“Thanks,” I said. “You too . . . Happy Solstice.”

Happy? Did I really say that? As I hung up, I wasn’t happy at all. On this solstice eve, I would still be declaring that I wanted a partner, but it wouldn’t be Dale. I let the waves wash over me—waves of tears, waves of lost hope—and went on arranging the celery, the hummus, the wine glasses, the kindling, trying to keep my tears off it all. It was the darkest night.

I had felt something with him. How did I let this happen? I was trying to protect myself by having a pre-date. He wasn’t supposed to reject me.

I then realized I was glad we didn’t have the dinner date and then get rejected. That would have hurt worse. I gathered my courage and vowed to stay open, even though my heart might get bruised along the way like this. My friends would be here soon. I knew that the light would return.

Read More: Love Lost and Found: High School Sweethearts Reunite Years Later

By Carolyn Lee Arnold


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