Dear Sasha: Will I Regret Being Quirkyalone in the Future?

by | Sep 10, 2018 | Dear Sasha, Quirkyalone, Relationships | 11 comments

photo by Natalia Brasil

Dear Sasha,
I’m 27, and I’m so thrilled to be a quirkyalone. I think it makes for a far more conscious, expressive and spontaneous life. Quirkyalonedom rules! But I struggle with thinking about what quirkyalonedom will be like in the future. How will it feel when I’m 50…70? Will the “this rules!” feeling that this is how life is meant to be lived dull over time? Will I look fondly on my quirkyalone twenties but think of myself as being naive to the future?
Thanks for the newsletter and the thoughts. Im happy to be part of it.

Hi Alex, Thanks for writing in with this excellent question. You sent this question two years ago and it took me two years to answer you because the question is so profound I only wanted to answer you when I was good and ready.

The first question I have for you is, What does quirkyalone mean to you?

To me, the essence of being quirkyalone is being true to yourself.

It’s hard to imagine how you can ever go wrong when you are true to yourself.

Being quirkyalone includes the possibility of being quirkytogether. So you really can’t go wrong when you stay true to your north star.

On the other hand, lots can go wrong when you lose touch with yourself: you might regret staying in a marriage with someone you’re not in love with because of your fear of loneliness, staying for years in a job you don’t believe in, or not taking the chance to express yourself to people you love.

What do people regret when they are on their deathbeds? Bronnie Ware is a palliative care nurse who spent years caring for patients in the last 12 weeks of their lives. She published a book called The Top Five Regrets of the Dying, and the most common regret was “I wish I’d had the courage to live a life true to myself, not the life others expected of me.” Another common regret: “I wish I’d had the courage to express my feelings.”

From an exhibit “Signs of Regret” in Washington DC based on Bronnie Ware’s book exploring regrets of the dying

Back to your pitch-perfect question. Is it possible to be naive about the future in your twenties? Sure, we are all naive when we are in our twenties. That’s the nature of being twentysomething. You don’t know yet what’s to come because you’re not there yet.

When I was in my twenties, I remember feeling that life was like Christmas Eve. The best was always to come and I didn’t have to make any limiting decisions yet. I remember an older man telling me at a party that I would not feel so romantic about being quirkyalone in my thirties. At the time I thought he was a jerk but when I got into my thirties, I thought, you know, he was right. My mid-thirties brought some rocky times. When I hit my mid-thirties most of my friends were getting married, buying homes, and having children. I wondered where I stood with all those life milestones and if I was being left behind.

Now I know that I wasn’t alone. The mid- to late-30s can be a stressful, dark passageway of the soul for single women–especially if you might want to have children but haven’t found a partner. People are starting to call this trend “social infertility” and it’s a problem that doesn’t get much attention. We only have so much time to find a partner and we have to decide. There are forks in the road: especially, have children or not. By 39, it can feel like time to pull the red alarm.

Men face their own pressures but men don’t usually perceive themselves as having the same biological clock pressure or “expiration date” in dating.

But just because life doesn’t happen on the prescribed timeline doesn’t mean life won’t happen. I wish I could have soothed my 35-year-old self from the position of where I stand now. I was really terrified about being aged out of the dating pool and being unloved for the rest of my life. I also worried my life would get dull without children, but that hasn’t been true at all. If anything my life has gotten more rewarding and my mother-friends convey their admiration for my more varied “selfish”(self-ful) life. (They love their children, but there are tradeoffs.)

I am proud of my life because I have been very intentional about my choices. I dug deep to ask myself what really matters and acted accordingly, even when it meant surfing with massive amounts of self-doubt. But because I am always checking in with myself on the why of what I’m doing at the deepest level I have no regrets. Here I’m talking about big decisions like where I put my creative energy, whether to be a self-employed entrepreneur or take the safer path of a job, the relationships I choose to invest in, and where I live.

If you don’t find someone to marry and have children by the end of your thirties turning the page into your forties may be a relief. If you were ambivalent about having children and it didn’t happen, now it’s no longer an option. There’s freedom in that clarity. You can go forward not scrutinizing every date to see if he will be “the one” to pop out a baby in the next two years–that’s a lot of pressure for dating! If the kids and marriage thing don’t happen, your forties can be a kind of rebirth. (I’m not saying this is easy. Many people go through grief over not having children and luckily there’s Jody Day’s Gateway Women community to help with releasing the grief.)

Then come the 50s, 60s, 70s, 80s, 90s, and who knows how long? I haven’t gotten to my fifties yet but I asked some of my newsletter subscribers to respond to your question and I love the nuanced responses I got from older women.

Leslie said:I turned 71 on October the 6th. I live on Cape Cod with my three elderly dachshunds and I am truly a Quirkyalone and have been since 1976 when I divorced my husband of only 6 years. I left him in Minneapolis and drove back to New England with a four-year-old son and three-year-old daughter, $100 in my pocket, no job, and no place to live. The rest is a very long story and I am now a grandmother of two, work part-time in the car business, sing in Sweet Adeline, an a cappella chorus, own a small dog-sitting business, am a hospice volunteer, and take courses in anything that interests me and am never lonely. 

I have had four or five serious relationships over the years but none ended in marriage. To the young lady who wrote you I truly believe that keeping your heart open may lead you to the perfect person but if not, a very satisfying life lies ahead if you stay true to yourself and never stop moving and learning.”

Sheila says:
“In response to Alex:
You can’t possibly predict anything about feelings that far ahead. You can’t predict next year, let alone decades in advance. 
I am 64 and quite like the label and status of quirkyalone. I’ve a sister, other family, friends and business associates, church community, customers, social media, God (not the least). So I’m not alone.
My husband died a few years ago and I’ve developed and adventured, wept and laughed, played and got myself into messes left right and centre, hated my singleness and aloneness sometimes BUT I would not have it any other way. So there.
love you all.
Sheila x”

Maybe you were asking, will I regret being quirkyalone now if I stay perpetually single?  I want to speak to you if you have this fear. It’s easy to shut down and give up on love because it hurts and it’s fatiguing to be on the lookout for a partner for years when you don’t find someone. This is a fatigue and angst that doesn’t get talked about much! On the other hand, if you really want a deep experience of love  don’t give up. Know it’s possible and maybe you just need to give it time and believe in yourself, your lovability, and your unique path in life.

Sara Eckel (author of the fantastic book It’s Not You: 27 (Wrong) Reasons You’re Single) argues that single women are far too likely to berate themselves with criticism to explain why they haven’t found a partner (with messages we pick up like lint from our culture like “you’re too picky, or desperate, or independent”) and I couldn’t agree more.

But I can say sometimes there may be particular reasons why we may find forming trusting, long-lasting healthy relationships challenging, based on who we are and the experiences we’ve had. It’s always time and energy well spent to reflect and do personal growth work to have better relationships. That’s been my story and the story of a number of my clients, and that’s some of the most valuable work you can do in a lifetime: to open yourself up for deeper love. People who have been in long relationships also often need to do healing relationship work–just because you have been in a long relationship doesn’t mean it’s particularly healthy.

Finally, I hear in your question one more question. Will I regret being quirkyalone if I wind up alone when I get to my 70s? Who will take care of me if I’m old and fragile? This is a topic we are going to have to address as a society because so many of us are going to be single in old age, whether we marry or not.  Our society is going to need new models for health care, mutual support, community and caregivers who receive a living wage.

It’s impossible to predict the future. You could meet the love of your life now and he or she could pass in his or her 50s. You could have children who are not suited to be caregivers. I understand wanting to control for the future. Certainly I do. But all we can really do is live and love moment by moment.

I hope these words have been more reassuring than scary as you think about the road ahead. I think avoiding regret is really about honesty and the courage to take risks. If you do cozy up with another human in a long-term relationship, you know you are with your partner because of love and desire, not fear of loneliness or to fulfill societal expectation. In every area of your life, be honest with yourself. Ask yourself what you want. Ask your body what it wants. If you put your heart into your life and relationships (of all kinds, including your relationship with yourself), even if you don’t get exactly what you wanted you will have nothing to regret. We don’t have total control over what happens in life. But if you get clear about what you want and live from your desires rather than fears, there can be no regrets, only lessons learned.

Do you have thoughts or a story for Alex? Please share with us in the comments.

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  1. Carissa

    I am quirkyalone and to-be quirkytogether in a few months as I stayed true to myself and what I wanted in a relationship. It was frustrating and relieving each time I thought I met the one but nope, not mine. I learned a lot along the way and when I was able to really let go and be fully myself around another – woo, it was bliss! At 47, I’ll be walking down the aisle knowing we love each other for who we really are – and not because of some fear of being alone. I’m most happy and proud that I made my own lifetime story of love of friends, family and adventures (including the Tango adventure).

    • Sasha Cagen

      Love your story so much Carissa! Happy to have gotten to meet you in person in Buenos Aires and through the Get Quirky class!

  2. Lindsay Livingston

    I am 67. I have tried marriage twice, tried living with men. I am happiest on my own. I have been purposefully single for the last 20 years. They have been the best most fulfilling years of my life. I just retired and moved permanently to Buenos Aires to dance tango until the end of my days. I bought an apartment and am looking forward to travel and new friends in the last part of my life.

  3. Sunny

    Dear Alex,
    Two years is a long time to wait for answers to your question. I hope you’re still following the thread here, and glean some wisdom from the replies to your question.
    As a 58-year old female, alone due to quirks unforeseen, some not of my making but some, yeah, mine albeit unconsciously created, I’ve been told I should write a book! For now, here are a few thoughts for you to chew on.
    Keep dreaming. Keep having goals. Keep your heart open, no matter how it gets hurt along the way.
    Celebrate each decade.
    Maybe you’ll still love quirky aloneness when you’re 70. Maybe you’ll tire of some aspects. But for now, don’t worry. You’re building a life you enjoy. As time goes on, you’ll continue to do so because you began early. “Teach a child in the way he should go, and when he is old he will not depart from it.” Holy Bible
    If a time comes when being quirkyalone is less pleasing to you, if your heart is open, you will continue to experience joy.

  4. Paula White

    Read The Year of Yes by Shonda Rhimes. She has some profound thoughts about being Quirkyalone. She said her parents are soulmates. They are both educators. They have 6 children. They think each other’s thoughts and finish each other’s sentences. She said that if she were to marry, she wanted a relationship EXACTLY like what they had.

    HOWEVER, she KNEW that relationships like this were few and far between.

    As a direct result, she placed her energy on becoming a television writer and she had 3 children on her own without getting married.

    I KNEW these things deep inside me, but to have her write it out deeply resonated with me.

    I just had to share.

  5. Sandy Lovejoy

    Very wise advice, Sasha! And it’s so interesting and reassuring hearing from people further along their life course reflecting on their choices. There is a lot to chew on.

  6. Paula Prober

    I’m 66 and quirkyalone. I’ve had 2 significant partnerships where I learned a lot. Never had kids. I’ve always known that motherhood was not for me. I’m very career focused and love my work as a psychotherapist-consultant-writer-blogger. I found the tango at age 47 and get some of my needs for touch, creative expression, and feeling-attractive-while-aging met that way. I’ve done years of different therapies as a way to heal from past trauma, find self-love, and live a fulfilling life. I’ve built a strong friendship network. I’m wanting a quirkytogether relationship and know that finding a deep, loving connection can happen at any age. I suspect that there’s a psycho-spiritual Mystery involved in bringing people together. So, I open to the Mystery, continue to soften my heart, and through my professional presence on social media, expect that my partner will find me when the time is right!

    • Sasha Cagen

      Hear hear on the psycho-spiritual mystery Paula. There is a mystery to it all. Thanks for sharing a bit of your story here!

  7. Tanya B

    There is so much to contemplate here, and I love all the ways this response is not full of easy answers. And also allows life to be beautiful even when way off “script”. Also, super admire this moment: “I am proud of my life because I have been very intentional about my choices. I dug deep to ask myself what really matters and acted accordingly, even when it meant surfing with massive amounts of self-doubt.”

  8. Richard Messum

    I’m 68 and perfectly happy on my own. I prefer it, i’m comfortable with it, and to be honest i don’t really enjoy the company of other people. I know that when you’re 27 it’s impossible to imagine what your life will be like forty years on: we change. Go with whatever changes and do what you think is best for you. Not highly profound; just my two cents.

  9. SKH

    Very powerful. Thank you.


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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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