My recent solo date: a fall walk down Eastern Parkway in Brooklyn.

Tired of Being Single? Start Dating Yourself

Smiley Poswolsky
Oct 21, 2014 · 4 min read

Let me preface this piece by saying that I’m 31, I’m single, I haven’t been in love in years, and I haven’t gone on a real date in months. And I’m happy.

It seems that every other conversation I have is with people my age freaking out about single. “Smiley, what am I gonna do, get on Tinder, is that all I have left?” “Smiley, how am I supposed to meet someone when everyone attractive and dateable is already taken?” “Smiley, I can’t go to another wedding without a +1, it’s embarrassing!” “Smiley, I want to have a family and I’m 32 and single, my life is worthless!”

These conversations often surprise me. First off, if so many amazing people are single, why is everyone having so much trouble meeting the right partner? I now keep a running tab in my journal of cool and clever people I know who are single and I cross-reference the list once every two weeks for potential matches — I’m like a boutique Hinge.

Second, and more alarming, is why people are so distraught about being single. I’ve spent the better part of the last year (okay, two years) (all right, fuck it, three years) single, and while I could make up a horror story about how miserable I was, the truth is I’ve never been happier. Rather than stress about how hard it was to meet the perfect woman at the age of 30, I decided to forget about dating all together.

Instead, I decided to start dating myself.

When you start dating yourself, your mindset shifts. Rather than define your own self-worth based on whether someone else swipes right at your photo or whether someone else wants to go home with you, you determine your own self-worth based on how you’re spending your time. You can commit to personal projects, set aside time for self-reflection and self-care, and discover new career aspirations. Instead of simply going through the motions, you’re in the driver’s seat of your own life.

If you’re struggling with online dating or stressing about being the only single person at your friend’s wedding (don’t worry that happened to me three times this summer!), my recommendation is to spend a few weeks dating yourself.

Treat yourself.

Take yourself out on your perfect date. Go out to your favorite restaurant, order exactly what you want to eat, and drink a glass of red wine. Buy yourself a new shirt or pair of shoes. Go to the bookstore and buy a new book you’re dying to read. Take yourself to a show this weekend — music, theater, comedy — whatever you love most. Go to a movie by yourself and sit in the exact seat you want to sit in. Go on an adventure to a place you’ve never been before.

Take care of yourself.

Go for a run. Take a long urban hike. Go to a yoga class you never have time to go to. Meditate. Take a nap in the sun. Take a nap in the shade. Take a bath. Get a massage. Cook your favorite meal. Order delivery and eat it in bed. Wake up early and read a book that has been sitting on your shelf for months. Stay up late and watch episodes of your favorite show on Netflix.

Create yourself.

Write in your journal. Write a blog post. Write a short story. Write a book (disclaimer: I did this and as a result was single for two years, so plan accordingly). Take a letterpress class. Paint. Draw. Take photos. Make a short film. Learn to code. Learn a new language. Design your new website. Come up with a business idea.

Engage yourself.

Find a friend working on a project that interests you and see how you can get involved. Volunteer in your community. Push yourself outside your comfort zone by going solo to a happy hour, party or event that sounds fun. Start a group meet-up for an activity you love like yoga, cooking, poetry, or graphic design.

See, being single isn’t so bad. If you’re in a relationship and jealous of all the fun us single people are having because we’re dating ourselves, you should be jealous. You’re missing out, SUCKER! Treat yourself! (And if you decide to break up with your girlfriend, let me know cause I have a huge crush on her.)

Don’t worry, it’s not permanent. I want someone to come home and snuggle with, just like everyone else. I want to have a family one day. I’m not telling you to give up sex or dating forever. I’m not telling you to abandon your life-long goal of being an amazing parent.

I’m just saying that dating yourself for a little while might help you discover who you are and what you want. It might help you stop worrying about what other people think of your sixth Tinder photo (or stress about whether you should even have a sixth Tinder photo — “who the hell has six Tinder photos?!”) and start thinking about how you want to spend your days. It might inspire you to explore a new passion or find a new job. It might give you the time to launch the project or embark on the adventure you’ve always dreamed of.

If you’re lucky, dating yourself might even bring you closer to the person you’ve been looking for.

Smiley is the author of The Quarter-Life Breakthrough, which is an Amazon bestseller. Follow him @whatsupsmiley and get free resources in his newsletter.

Smiley Poswolsky

Written by

Author of The Quarter-Life Breakthrough. Speaker. Millennial workplace expert.

Let’s get coffee

Stories and thoughts about dating. Get updates via Twitter @LetsGetACoffee

Smiley Poswolsky

Written by

Author of The Quarter-Life Breakthrough. Speaker. Millennial workplace expert.

Let’s get coffee

Stories and thoughts about dating. Get updates via Twitter @LetsGetACoffee

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