7 Things I Learned from Dating and Writing

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Carolyn Arnold

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7 Things I Learned from Dating and Writing

Carolyn Lee Arnold’s new book, Fifty Dates After Fifty, has been called a “frolicking, racy memoir.” As a fifty-something woman, Carolyn learned that you must kiss a lot of frogs to find a prince—so the key is to enjoy the frogs along the way. And it turns out that first dates are a lot like first drafts. Many thanks, Carolyn, for your vibrant wisdom on both fronts!

Dating and writing have a lot in common:  Attitude is everything, persistence is key, and loving yourself is required.  Dating and writing can feel easy and exciting (attitude!) or like a lot of hard grueling work (persistence!). Both are true, so the more self-love the better.

In my late 50s, I challenged myself to go on 50 first dates to find a committed male partner. It took me 2.5 years and 50 dates to find him, and we’ve been happily together for 11 years. During those years, I wrote and published a book about my dating journey, called Fifty First Dates After Fifty: A Memoir. Here is what I learned about dating and writing.


These are the attitudes that kept me going on my dating and writing journeys, even when the going got tough:

  • For both journeys, I was inspired by my goals: 1) to find a partner and 2) to inspire older women to enjoy dating. When I got discouraged and wondered why I was going on yet another date, or why I felt the need to finish and publish my book, I would remind myself of my purpose, and that kept me going.
  • Just as important as having a goal that pulled me forward was enjoying each step of the process. This meant feeling the joy in each date, whether or not the man was ‘partner material.’ I tried to expand my ‘type’ of man by going out with those I would not usually date, so I also brought curiosity to each date to find out what I liked about them (See Carolyn’s blog post: “Why 50 First Dates?”). In writing, I found joy in getting my stories down on paper in a way that delighted me, separate from any feedback from others. I also enjoyed reading my stories out loud to others to see what delighted them. If I had not enjoyed the process, I could not have kept dating or writing.
  • Optimism and confidence. Although I had setbacks when I felt discouraged and unsure, I still believed that I would find a partner and that sharing my stories was worthwhile.  My confidence grew as I put more time into dating and writing.  I didn’t envision the type of partner I wanted until halfway through my dating project, and I didn’t imagine that I’d write a book until I’d been writing down my dating stories for over a year.
  • Persistence is an attitude, but it is also action: Going to a party alone on Valentine’s Day because I needed to meet new men.  Leaving a party of friends to go to a singles night at a retreat center.  Spending Sundays writing even when my friends invited me on enticing adventures. As one of my teachers said, “What are you going to say ‘no’ to, in order to get the book written?”  I said no to a lot of activities so I could make time to write.  And I said yes to classes, retreats, and writing groups that would help me get my book written.
  • Loving myself. Self-love is an inside job, but it can be grown and strengthened from the outside. Going to personal growth workshops that taught me how to be more loving to myself and others gave me tools to love myself fiercely through the ups and downs of dating and writing. (See Carolyn’s blog post, “Ten Ways Relationship Workshops Helped Me Date”) I learned to appreciate the goodness in myself and others, refrain from judging, and nurture myself along the way. With those tools, I was able to comfort myself after bad dating experiences, or when teachers or friends didn’t like my writing. Part of loving myself was seeking out positive, supportive friends and writing colleagues.
  • Not taking things personally. This is a crucial skill that I learned in personal growth workshops. Everyone is living their own life, with their own experiences and perspectives. Only they can say what they need in dating or what they like in writing, and it might be different from what I need and like. Their choices have more to do with them than with me. So I understood that if they rejected me in dating, it had to do with their life path, and was not a judgement about me. My memoir includes several examples of how I handled those rejections.
  • If a teacher or classmate did not like my stories it was often a reflection of their needs, not a judgement on my writing. For instance, an early teacher asked about one of my dating stories: “Didn’t you see that the guy was a jerk?” At the next class she read from one of her dating stories about the way she had responded to a jerk. It was not how I would have responded. One of my main purposes in writing was to show it was possible to appreciate each man for what he offered, not what he lacked. Although she was there to help me improve my writing, her experiences got in the way. I found other teachers who could help me hone my story from my perspective.

Did I ever feel stuck?

In dating, I did get discouraged about whether I’d ever find a partner, but I never felt stuck, because my goal of fifty dates pulled me forward. There was always the next date to find or go on.

In writing, I got stuck when I’d gotten as far as I could with my current teacher or writing group and needed more feedback to improve my manuscript. I wrote the first draft of my dating adventures by taking class after class in creative non-fiction for several years, where I got feedback on between five and ten pages at a time. I also had a writing partner for a summer and exchanged a chapter a week. But at some point, I needed feedback on larger parts of the manuscript. I needed to expand my pool of editors, writing teachers, classes, and communities.

I found one of my most pivotal editors in a booth at a local book festival. She became the first person to read my entire manuscript, and the advice she gave helped shape the book. When I finished the next version, I found a small class for writers like me with an unfinished manuscript – we shared the core 125 pages of our books and got feedback from the teacher and each other. When I had a complete first draft, I attended the book launch of a friend, which led me to her writing teacher, which led me to that teacher’s five-day writing retreat, where I met her teaching partner, who became my favorite writing teacher. Taking her classes improved my writing enough to give my dating book to my final editor, and guided me to produce the first draft of my next memoir.  Those classes put me in the center of a writing community that has become my own. It paid to keep looking for the feedback and support I needed.

Recommendations for dating and writing

Do you want to date, or write, or both? Here are my top recommendations for women over fifty:

  • Start now and create a way to keep doing it!

Finding a partner is a numbers game – you have to go on a lot of dates to find the person who is right for you, so the sooner you start, the more people you will meet, and the better you will become at dating. Dating is a skill that takes practice. What will make you keep dating? For me, it was setting a goal, like a number of dates or a time period.

Writing a book happens by building it scene by scene, so don’t think about the whole book—just start writing the scenes that are alive in you now. Writing is also a skill that takes practice. Find a structure that keeps you writing, like a daily time period, or a number of words or scenes a week, or classes with deadlines.

  • Build in support.

For dating, be sure you have supportive friends, groups, and/or a larger community who will love and support you during your dating journey, with the positive attitudes you need to keep dating through the ups and downs. (See Carolyn’s blog post “Six Types of Dating Support”)

For writing, take beginning classes with supportive, encouraging teachers who know how to nurture your writing skills and aspirations. In these classes, find other writers who want to form groups or dyads for support and feedback.

  • Learn the standard practices in your genre (memoir, fiction).

Read read read! Read books in your genre and read books about the craft of your genre. Study memoirs or short stories for their craft. Find ways to practice the best techniques by yourself or with a teacher. You need to know what has gone before and how your story or writing fits in. There is no need invent writing techniques or story structures. There are plenty of basics to learn before you branch out.

  • Take classes and form writing groups or partnerships.

Classes have built-in deadlines and feedback that keep you improving and moving forward. Deadlines were what kept me writing late at night on a worknight, or giving up Sunday excursions to write. In these classes, identify supportive classmates who want to form writing groups or dyads.

  • Get feedback from a variety of people.

Get your writing in front of a variety of teachers and readers to get feedback, especially from those in your target audience. Not everyone will love your stories or writing, but some will. Take classes that are progressively more challenging so you get feedback appropriate to your level of writing from more than one teacher and reader.

  • Read your writing out loud.

Read 1- to 3-minute snippets to friends or in supportive groups or at open mics. You will see what works in the writing, and have the thrill of in-person accolades along the way. Be sure to be self-loving if they don’t respond as enthusiastically as you hoped.

Starting a dating journey and learning to write may be your biggest challenges ever. They will also be the most rewarding, for you will meet people and learn attitudes and skills that will change your life, whether or not you find a partner or write a book. A success guru once said, “Become a millionaire not for the money, but for whom you will become along the way.” Start dating or writing for the person you will become as you practice optimism, persistence, self-love, dating and writing skills, and the enjoyment of every step along the way.



Carolyn Lee Arnold is the author of Fifty First Dates after Fifty: A Memoir, the story of how she turned dating into a sexy, enjoyable quest to find her unique partner. Her book has received awards for its portrayal of Sexuality and Relationships, and for being Inspirational and Motivational. Her dating project drew upon her thirty years as a social science researcher and ten years as a relationship workshop assistant. A native Californian from Los Angeles, Carolyn found her true home in the San Francisco Bay Area, where she prepared for dating and life by attending spiritual ceremonies, working as a crisis counselor, leading women’s backpacking trips, and earning graduate degrees in women’s studies and educational research. She blogs about the things she learned about dating and life, and lives in the Bay Area with her partner, one of her fifty dates. To see her book, blog, dating tips and dating resources, visit carolynleearnold.com. Buy her book here. And sign up for her blog to receive the detailed version of Carolyn’s ten dating tips!

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