How to Fall in Love with Yourself While You Look for Love

Dating is difficult. Inevitably, we get rejected. Or we reject. We want to keep our hearts open but they keep getting smushed. What does it take to fall—and stay—in love with yourself while you look for love?

I’m doing a series of profiles and interviews of Quirky Characters on my website and I’m sharing this one on For Quirky Character Number 2, I want to introduce you to Carolyn. Carolyn, 61, is an educational researcher. We met in a memoir-writing class taught by Laura Fraser earlier this year and since we met we have been giving each other feedback on our projects. Carolyn is writing a memoir about her Fifty First Dates Project while I am writing a memoir about searching for happiness through the body in South America. 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.

Carolyn shows us how it's done

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.

Where did you find these men?
I am part of a big community of people who have done personal growth workshops through HAI, Human Awareness Institute. The workshops are about relationships, love, intimacy, and sexuality. About 50,000 people, and a lot of people in the Bay Area, have done them over the years. We keep in touch through parties and gatherings and I help with the workshops, so at least a half of my dates were from that community. Others were the usual way. I stayed with my interests: hiking and spirituality. I went to spiritual places with singles’ nights; the Sierra Club has Sierra Singles. I was open to meeting people wherever, in the grocery store. I met someone at a real estate seminar in Mexico. Different random places. I also did some online dating.

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.

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Posted in Dating, Personal Growth, Quirkytogether, Single Life
3 comments on “How to Fall in Love with Yourself While You Look for Love
  1. laura says:

    Thankyou so much for sharing this story Carolyn. After leaving a my controlling doctor husband after 25 years, two years ago,this story has given me the confidence to try an approach where I will still feel I retain my power. Trust is a huge issue for me and after being told that I was stupid and only good enough to stay home ,raise children and look after my husband; I focused the first two years on harm minimisation for the kids and throwing myself into my bachelor of nursing degree. I am a very sensual, tactic person who chose to try an fix a damaged, aspergers man for most of my life(with only one partner before him !) Part of me is desparate to go out and start on the 50 and part of me is afraid of getting rejected. Your story makes me want to just get out and experiment. Thankyou :)

  2. Carolyn says:


    I’m so glad you are inspired by my story! I wish you the best in your journey of dating and regaining the celebration of your own beauty, value, and sensuality. I’m so glad that this helps you see a way to do that in a self-empowering way.

    If you want an additional way to learn how to love and value yourself, and to learn and practice healthy dating and relating skills, I’d also highly recommend the HAI ( workshops.

    Thanks so much for writing! You inspire me to get keep going on my book so that I can get the story of my 50 dates out there.


  3. christy says:

    Carolyn!!! :) Way to go!!! I love this story of discovery about yourself and how you love life, yourself and your partner! I cannot really begin to explain all of the insight that reading this has caused me to have into my own way of loving as well as who I am in love. I can say that I see more clearly that I love – love – love to understand and delve into subjects that interest me… partners included… and people in general interest me… I truly find others fascinating to learn about! I have recently realized that I am not ready to “settle” for a connection of subdued interest and so that is how I ended up finding this website… someone described me as “obsessive” and after reading your article I know that that is not only not a bad thing… but it is a great thing to be interested in life, myself, and others with a depth that most don’t really engage one another in! I love that about myself ! Thank you so much for writing with such openness about you… I felt it ! Congratulations to you and to number 49! :) Lucky guy to have a woman that knows herself so well!

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What’s a quirkyalone?

A quirkyalone is a person who enjoys being single (or spending time alone) and so prefers to wait for the right person to come along rather than dating indiscriminately. Quirkyalones prefer to be single rather than settle.
Quirkyalones can also be married or in a committed relationship (quirkytogether). You can be a man or a woman, any age.
Quirkyalone is ultimately a philosophy about finding happiness within yourself whether you’re single or in a relationship.

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