Carolyn and Her 50 First Dates Project, or, How to Fall in Love with Yourself While You Look for a Partner

by | Nov 29, 2012 | Advice, Dating, Sex | 5 comments

Dating is not for the faint of heart. Inevitably, dating means putting your heart out there on the line for people you are just getting to know. Along the way, we may get rejected. Or we may reject. The whole experience can make you want to retreat and watch Netflix for the rest of your life. What does it take to stay upbeat, treat dating as a way to expand your life, and even fall—and stay—in love with yourself while you look for love?

I’m doing a series of profiles and interviews of Quirky Characters. For Quirky Character Number 2, I want to introduce you to Carolyn. Carolyn, 61, is a social scientist. We met in a memoir-writing class taught by Laura Fraser earlier this year and since then I’ve been giving Carolyn feedback about an exciting writing project–so exciting I want to share it with you here.

Carolyn is writing a memoir about her Fifty First Dates Project. When she was in her late 50s, Carolyn decided to go on 50 dates to find her next partner. I’ve loved getting to know Carolyn giving her feedback on her writing; I’ve gotten to absorb her philosophy and it’s helped me to be wiser and more positive in my own approach to dating. So I want to share her with you.

Here’s our interview on what it takes to stay in love with yourself while you look for love.


What made you decide to go on 50 First Dates to find your next partner?

I was in a relationship with a wonderful man for eight years during my fifties, and I thought he was perfect for me but there were also limitations and were we growing apart. He lived in Hawaii, and I lived in the Bay Area, California; we had a long-distance relationship and he did not want to commit to a long-term relationship. I wanted someone who lived closer and to have a deeper relationship.

I thought, How am I going to get over him and find someone else when he still seems like the perfect partner for me? I decided I would need to go out with a lot of men, and I decided 50, not just as a way to find a partner but also to break open my idea of the perfect man. We all have a type, sometimes we can’t think beyond that type. My goal was to experience lots of different types of men, in terms of personality, lifestyle, life plan, jobs, ways of living.

Where did you get the idea of fifty?
There was a movie 50 First Dates that I saw on an airplane without sound. The number just stuck in my mind. I’m a statistician; fifty is a significant number for results. In real estate you look at 100 houses before buying. I thought 50 would be a good start.

Didn’t you get tired of going out on dates?
I actually found it energizing to have a goal. I have found in dating that if the man doesn’t like me or I don’t like them I get discouraged, so instead this project gave me this perspective that I didn’t have to take any one of the dates too seriously. I had more of a curiosity about what was it like to be with each person. I got to observe myself more. I had a momentum and optimism that carried me forward.

Originally Peter was going to go travel in Europe for eight months. My goal was to find out if there was someone better than Peter. If I don’t find someone better then I would just get back together with him. Originally I thought 50 dates in 8 months. I didn’t do the math. In the end I did 50 first dates in about two and a half years.

What did you learn about yourself?
I’m not sure that I learned anything about myself but I affirmed what I already knew about my ability to make things happen and to love myself. I was in my late 50s and I knew how much we get discouraged dating. I found ways to love myself when I have seen myself and other women crumpling in dating.

I learned this method for approaching life: going for something I want but not getting too attached to having it right away but enjoying the process along the way. And to love myself during the process even when it got discouraging or sad. There were times when I missed Peter and I thought, I want him back. I felt that half of the journey. But I also kept continuing on with my spirits up. I would get discouraged and lonely and I would get more energy from going forward; there was always the next date; maybe this would be different.

When I look back on the dates, I see that a lot of men did not want to be with me. I was surprised and at times hurt. I gathered my friends who helped support me and helped me cry it out. But at the time I didn’t feel like I was getting rejected that much. Because I had the goal I just kept moving on and there was something in that moving on that buoyed me.

You are a proponent in your own life of having lovers while looking for a partner.
It’s a personal choice. I made a choice in my 40s. I realized I am a very sensual person. I love touch. I love being sexual. I love sleeping with someone. I made that decision that I want to be sensual and sexual in my life even if I don’t have a life partner. Since my 40s I made it a point to have a lover even if they are not perfect; of course it has to be someone I love and feel close to even if it is not the relationship.

When I started dating some of my early dates became my lovers. They were crucial supports. It was clear they would no be my long-term partner because they were too young or in a primary relationship or they didn’t have the qualities for long-term but they were perfect for staying sensual and sexual during my late 50s. As I hit menopause and my libido was dropping I didn’t want to lose that touch and sexuality.

Sometimes I would meet someone I wanted to be sexual with and I needed to explain that I had lovers that I was not going to give up. Some men had a problem with that. If I had felt more drawn to the person I would have felt more comfortable giving my lovers up. I always told people I was seeing other people. Some men who were more traditional assumed I would stop seeing other lovers if I slept with them.

On what date did you meet your partner?
Date 49. I got more serious in the 40s. I was starting to pick men who were good potentials for partners. At first I was not interested in him, but one night we met at a party in a group and we just both said, Wow, we need to get together. He was cute, smart, heartful, and we had a spark even when our hands touched for the first time.

Date 49 and Carolyn

What advice do you have for people who are dating?
When you are looking for a partner there are a lot of people in the world. Dating is a process of checking people out and who you want to be close to. It’s really good to not focus on one person right away. Dates should be about gathering information and the main info is about yourself, how you are with certain people. By looking at it than information gathering it feels more neutral and fun. What is it like to go on a hike or a dinner with this person? What do I like or not like? Whatever can give an attitude of curiosity and less an investment in a certain outcome helps dating.

This goal thing doesn’t work for everyone. I’m a statistician and I like big numbers. Having a goal helped me have a certain attitude of seeing every date as an experience of getting to know someone else and myself and from a curious point of view rather than a longing point of view.

I see other women dating one or two people and stopping and settling with someone who is not quite the right person. I don’t mean you have to sleep with them, just experiencing them one on one in a social situation.

My other tip is to have a practice to affirm yourself. I was skeptical but affirmations and visioning really work. During the second year I did a formal course to envision my partner and envision the feeling of what it would be like to be with him. I wrote descriptions of what the relationship would feel like and put them up on my bathroom wall and I ended up with someone who was very close to what I envisioned.

Ask yourself, How can I celebrate myself in this whole process? We need to celebrate ourselves while we are in a relationship too. I was enjoying being single. I would say, “This is my life, I go out on dates and my dates and lovers are the relationship I have.” Accepting my life and celebrating it got me more open to my partner when I met him.


  1. jen

    Can we get a follow up post on this one….

    i need to satisfy my cynical side 🙂

    • Carolyn

      Hi Jen!
      Date number 49 and I are coming up on our 4th anniversary! We both continue to be amazed at how perfect for each other we are in our quirkiness as individuals and as a couple. If I had not found him, however, I was getting ready to do 50 more dates, since I enjoyed the process. Best wishes to you!

  2. sasha

    Jen, what do you want to know? 😉 Carolyn met her partner and there are many more details in that story. She’s writing a book about it all.

  3. Molly

    Hi Jen,

    I was inspired by the approach you decided on to find your life partner. After
    2 marriages I find for the most part I have enjoyed this 13 year period of being
    single. But recently I am finding myself ready to try again to ‘connect’. In the past I have given up very quickly on this process. Your experience has given me
    another perspective.

    Thank you for sharing it.


  4. MEL

    At my age (early 60’s) in my conservative area, I very much doubt I could find five unattached men to date much less 50. Dating someone very long distance would not be an option for me unless all I wanted was a nice pen/phone friend.
    While I don’t mind dating different people at the same time, I very much dislike the idea of seeing men who have a current primary attachments (married or otherwise) to other. Been there, done that, it stank.The guy always treated me as if I were a piece on the side and not worthy of anything but sneaky sex.
    At 20 or even 30, dating just for fun was cool. But at my age, I simply haven’t the energy to date around like I did back then. And after all these years, my heart couldn’t take the emotional pounding that a younger person could weather.


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Hi! I’m Sasha

Executive and Life Coach on a mission to help women connect with their bodies to pursue their truest desires in the bedroom and the world.

Author of Quirkyalone: A Manifesto for Uncompromising Romantics (HarperCollins) + To-Do List: From Buying Milk to Finding a Soul Mate, What Our Lists Reveal About Us (Simon & Schuster).

At work on a memoir called Wet, about adventures in healing through sensuality.

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