The Art of Dating Yourself

I shy away from giving advice on this blog, mostly because I’m not qualified to advise people on the topics of which I discuss.

Dating? Relationships? Why would I encourage people to take advice about such subjects from a girl like me who is blogging at a link like this?

Don’t worry, I wouldn’t either.

I’ve instead taken the stance that this particular blog about dating and relationships is a place where I share my stories about what I learned about myself after loving and losing over the years in the form of stories that are true, or at least as true as I remember them. I’ve also done my best to remain as biased as I can be despite this being MY BLOG.

In saying that, what I hope happens is for my readers to gain whatever insight, lessons or tough love that they can gather ON THEIR OWN from some of the mistakes I might have made without feeling like it’s being pressed on.

I’m only telling a story.  Insta

However there is one area that I’m confident about offering some insight (and dare I say ADVICE), and that is the fine art of being alone, because while I’m not an expert at dating other people, I’m a master at dating myself.

Despite no fault of my own and for some reason unbeknownst to me, my parents decided that one was enough. One kid, one monster, one little person demanding their attention despite my pleas and wishes for a relatable playmate. To make up for the fact that I was the only kid, my parents naturally wanted the best for me and made great sacrifices to make that so. This “best” included sending me to private school that carried just enough prestige to make me different from all the other “public school” kids that ran the neighborhood at the time. Public school kids didn’t play with the private school kids, at least the little heathens that lived next to me didn’t.

But what about relatives you ask? Was anyone my age at the time? What about cousins?

There were none until I entered my teen years when the rest of my family decided that they should make some.

Needless to say, there were copious amount of times when I had to entertain myself with barbies, legos and my favorite books on tape with nothing but my own solitude to keep me company and Eric Carmen’s “All By Myself” symbolically playing in the background.

Don’t get me wrong, my parents did step it up in providing me with the Suncompanionship that I so needed at the time, even if that meant committing a whole night to yet another game of Monopoly. (Why must her favorite game also be the longest?) However, there always seemed to be more urgent, more adult things for them to deal with, and lets be honest, sometimes I just didn’t want to hang out with them despite their effort to include me in whatever it was that they were doing.  At times, if we weren’t doing an activity that I was organizing, I did not want to do it. For instance, an activity my mom organized for me was the fascinating task of hanging socks on my own clothesline as I stood next to her while she did the same on a much higher one. My mom tells this story fondly, but I fail to tell it as fondly.

Thankfully my parents realized very early that there were in fact more interesting things that I wanted to do, but rather than encouraging me to, “Let my freak flag fly,” because I wasn’t that type of kid, my parents forced ME TO FLY on my own in order to discover the things that I loved to do, even if that meant that I didn’t know anyone or have anyone to do them with.

“You want to be a Girl Scout? Go!” “You want to play the violin even though no one you know does? Ok!”

“You want to be a Girl Scout? Go!” “You want to play the violin even though no one you know does? Ok!”

“What else do you want to do, Jennifer?”

As I got older, this theme of doing what I loved even though I didn’t have anyone to do them with would continue through college and beyond despite the insecurities and hang-ups that I faced whenever I veered out of my comfort zone.

What will people think? Will they wonder why I’m alone? Will they wonder why this girl doesn’t have any friends to hang out with?

And for awhile, especially when I moved crossed country after college, that fact was true. For a long time, I didn’t have any friends. I had to go by myself to do things or I would end up doing NOTHING.

Were there times when I would call my parents in tears about my loneliness? Absolutely!

How many times? Too many to count.

But the important thing is, I got through years of this that left me with an important life lesson. That life lesson being –

I learned who I was by being in my own company.

I also stopped carrying those insecurities about what people thought and started enjoying all those places, all those dinners,  movies, and concerts (where I went by myself) even more.

I learned how to be ok alone by being just that, ALONE.

I eventually made friends (thankfully!) and with that came the relief that finally I had people to call! Finally I had phone numbers that I could text when I found something that I wanted to do. I didn’t have to go alone!

However I found that all those years of venturing out of my social comfort zone was still engrained in me. It was now who I was. I was someone who still liked doing some things by myself and a person who didn’t need an entourage or a buddy to decide what I wanted to do.

When asked, “Why I didn’t you invite me?”

I said, “Don’t feel bad. I didn’t invite anyone.”

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J is a happily single 30-something currently documenting her stories of love and loss. Her blog, “I Quit Dating” features excerpts of her journey as she reflects on the lessons learned from the men she loved. A complete collection of essays detailing her walk away from finding Mr. Right in order to pursue a more fulfilled life will be self-published next year. She recently moved from Los Angeles to New York. Contact: iquitdating (@)

22 thoughts on “The Art of Dating Yourself”

    1. It’s amazing…but a beast!! As much as I loved it, I wish I picked an easier instrument. I put so many hours and years into it and still could put in more. You really have to stick with it. I actually didn’t know that about Sherlock Homes!


      1. That’s very sweet. Thank you. While I always longed to be better, there is a sense of accomplishment that I know how to play at all. There is a reason they call it the devil’s instrument.


  1. Brilliant insight. I am an only child and never thought it about that way but now that I’ve had a chance to reflect on it, perhaps it did ‘prepare’ me to be who I am today. After having moved from my home country with two bags and a laptop, even when I thought I couldn’t do it, but I did, depending on absolutely no one but myself. And it’s amazing how far I’ve gone and how much I’ve achieved 🙂 The art of dating our own selves is an art that everyone should master, it prepares us to date someone else when the time is right.


  2. I agree that it’s important to learn to live with oneself. There’s nothing wrong in being alone. I guess that it’s the best thing a person can do, to get to know themselves, before they decide to start a life with somebody else. Even if there will be no somebody else, it’s simply one of the best gifts we can give ourselves – to accept ourselves when we are alone.


    1. Thanks so much for coming by! I know from your blog that you follow a ton, so I appreciate the read and encouragement. Yes…I hope book worthy!….I only need about 70,000 more words or so….:-O No problem! Ha!


  3. A brilliant post, it’s nice to know I am not alone with my insecurities. I have recently moved to a new area and yet again I am going to have to do the alone walking into the room thing, and I’ve had enough of it!!


    1. I think I’ve grown through that. I used to hate it as I mentioned….but now i dont hate it anymore. All from practice and being able to enjoy where I am. Lots and lots of practice.


      1. I am getting better. Interestingly I found it easier doing things alone when I was in a relationship. Because I didn’t care what I did or what people thought I quite happily went out for dinner to a restaurant with a book and just sat in the corner. Perhaps I need to do that again

        Liked by 1 person

  4. At times I don’t want to dispel advice. Especially with my failures, why should anyone listen to me, but then I made another discovery. You see while I might keep making the same mistakes, it doesn’t mean you will too. I keep making the same mistakes because of something I’m not doing. If you’re able to persevere where I failed, then perhaps my advice will work for you.
    I started writing because I had ideas that came to me, that weren’t always useful to me, but sometimes it was a catalyst for change to others. While writing is a way to get some thoughts out of my own head, it’s not just about me. Sometimes I’m very perceptive, and I’m intuitive about what’s going on in others lives.
    Lol so my advice to you is to write about things that inspire you, and let it impact others where it will. I’m not sure what your belief system is, but I’ve learnt that The Universe/God/Spiritually will give you what you need, when you need it most. Sometimes the message comes from an unlikely source. It’s not up to you and I if we’re to be used as a vessel, we just have to open ourselves to it.


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