Fifty Dates After Fifty

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Carolyn Lee Arnold went on fifty first dates after fifty to find her partner. Listen to this episode to find out what happened!

Carolyn Lee Arnold is a writer, hiker, relationship workshop assistant, and former educational researcher. Fifty First Dates After Fifty is about an experiment she set up for dating men. Before that, she spent 18 years identifying as a lesbian feminist. Still a feminist, she lives in the San Francisco Bay Area.

In this episode of Last First Date Radio:

  • Why Carolyn wrote a book about her fifty dates after fifty
  • How setting a goal of 50 dates made dating more enjoyable
  • The workshops Carolyn attended that helped her learn more about love, intimacy, and sexuality
  • How dating married or unavailable men helped her on her journey to love
  • The lessons she learned from her dating research project
  • How she found the man she’s with now
  • What you can learn from this book to help you enjoy the dating process

Fifty Dates After Fifty

Why did you write this book?

I wrote it after I had gone on my fifty first dates project. It buffered me from many of the pitfalls of dating, like putting all your eggs in one basket, or not even starting dating because we get so picky about dating. I thought of it as a research project. I had fun dating in my late fifties, unlike many of the women I know. I wanted to share my great experience.

How did setting a goal of 50 dates make dating more enjoyable?

I was trying to get over my previous boyfriend, but we ended up having different life goals, even though we still loved each other. I had to have a lot of different types of men to move past this relationship. I thought I needed to go on a lot of dates to find love. Fifty is a significant sample. 

When you started this dating project, you had done ten years of relationship workshops on love, intimacy, and sexuality. What skills from those workshops did you bring into dating?

The Human Awareness Institute helped me develop the skills I needed for relationships. They taught us to love ourselves and appreciate others. 

I wasn’t very confident when I started dating men after being a Lesbian. The workshops helped me, and then I volunteered to understand the principles: clear communication, self care, non sexual touch, and appreciation.

You consciously chose to have lovers and to date married men during this dating project who were not going to be your partner. Why did you do that and how did it help your dating?

It had to do with my mindset. I respected people’s relationships. I did want to date a variety of men. Every date didn’t have to be a potential partner. It was about the experience. Some of the men were married, and I knew the couples, and we respected the relationships. I protected myself by not going into the longing place of imagining the person would be perfect for me. Did I have fun, did he bring out the best in me? I took bits and pieces to create the image of who I wanted to date.

Since this was a research project, what did you learn about what type of partner and relationship you wanted, and how did you know when you found him?

The goal of fifty kept the momentum going. It made it lighter and helped me find my partner. The experience of dating many different types helped me discover who would be best suited for me. I found many partial partners, not complete partners.

I met my partner pretty early on, and I didn’t think he’d be good. He wasn’t available at the time, and I wasn’t interested. When I found out his marriage was ending, I looked at him more closely. I didn’t know he’d work out. We had an all day date. We went bike riding, a memorial service, and an Oscar party, which helped us get to know many sides of each other. It was cumulative. 

What advice do you have for anyone who wants to go on their last first date?

Vision what your life would be like with a partner. Get specific, even if you’re scared to do it. Have a support group for dating, whether it’s with a coach or with friends. Enjoy your life all along the dating process. Love yourself first, but not in a vacuum. Be around people who reflect the best in you. It’s a numbers game, and you need to date a lot and prepare for the long game.

Connect with Carolyn at and at the bottom of the page, when you sign up for her newsletter, you’ll get a free guide to ten dating tips. If you preorder by October 15th, send Carolyn a screenshot to and you’ll get the first few chapters for free to start reading while you’re waiting for the book to be published in November. 

Instagram @carolyn.lee.arnold 


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