The Subtle Art of Dating Yourself

A How-To Guide For Modern Women

I might be what they call a “serial dater.”

Already, this week I’ve been out on multiple dates (and it’s only Wednesday). Right this very moment, I’m sitting in a trendy little bistro on Via Ghibbellina with a freshly poured glass of red wine in front of me. Across from me? An empty chair. My “date” isn’t on the way, nor is he late, or in the bathroom. My date is typing these words right now. My date is me.

I’ve been going steady with myself for going on 10 years now. You could say, it’s getting pretty serious. It all started when I was 18 and moved away from home for the very first time. In a city full of strangers and an impending case of cabin fever, I left my little basement suite to meet myself, exactly where I was at: lonely, lost, and looking for (self)love.

I drove around for hours that day. Unsure of where I was going and unsure of who I would find when I got there. When I finally arrived — at a strip mall that housed a pizza joint, of all places — I sat myself down at a table for one, ordered a pizza big enough for two and resisted the urge to look at my phone for three whole hours. If I’m making it sound romantic, let me assure you…it was not.

Not only had I convinced myself that every time my waitress went back to the kitchen she was probably making fun of me for being alone, but I was completely at a loss for how to handle myself. Like, what should I do with my hands (do people actually twiddle their thumbs?), and where should I look, and oh gawd, I’m spending way too much time in my own head.

I’m not going to sugarcoat things for you. It was wholly uncomfortable. While I’d spent time alone before — painting in my bedroom for hours as a teenager, or running errands, or studying solo at the Starbucks near my house — I’d never been this alone. I’d never been this far from home, from family, from friends. I’d never truly known the heavy silence of distance, or been forced to rely on solely myself for company, conversation, and entertainment.

In the history of bad first dates, my first date with myself had not gone well. I had been brimming with nerves, the *very* awkward silences were too many to count and to top it all off I got stuck with the bill. BUT. Always one for second chances (and at a loss for what else to do with myself), I tried it again. And again. And again.

I took myself out to an art gallery.

I went for a walk along the breakwater.

I spent an afternoon at the movies — popcorn and all!

Eventually. I did make beautiful, lifelong friends in my new city. But by that time, I was also in a healthy, stable, committed relationship with myself and reaping all the benefits.

Pic via Instagram.

The Benefits Of Dating Yourself

I know, I know. The whole idea can be totally intimidating at first. And perhaps spending your evening solo sounds like a lame excuse for a Friday night (especially when you’ve got a girl-gang going out, and an S.O. dying to see you), but the benefits of dating yourself are truly too good to ignore.

  • Dating yourself strengthens your sense of independence.
  • Dating yourself pushes you outside of your comfort zone (and we all know what happens there).
  • Dating yourself build confidence.
  • Dating yourself results in increased self-awareness (in other words, you learn a lot about yourself).
  • Dating yourself provides you with the perfect opportunity for introspection and introspection = growth.

When you cultivate an open and honest relationship with yourself, you learn that you are a whole and complete person on your own, that you are the main source of love in your life, and that you don’t need anybody else to have a “good time” (even on Friday nights).

How To Date Yourself

Pic via Instagram.

1. Set a Date and Schedule it in Your Planner

It’s way too easy to back out of something when you’re not letting anyone down. But please, don’t be the girl who flakes on herself. You owe this time to yourself, for reasons you probably won’t even understand until you’ve experienced the magic of truly getting to know yourself.

So do yourself a favor, RN. Pick a date and put it on the calendar. Write it in permanent ink. Set a reminder on your phone. Leave a sticky note on your fridge. Plan for it.

Pro Tip: If this is a first-date situation, the act of planning ahead for it also allows you the time to mentally prepare yourself for the adventure you’re about to embark on.

2. Go Prepared

Speaking of preparation… If this is your first time, it might feel a little awkward. Rewind to the image of 18-year-old me twiddling my thumbs while waiting for pizza in a strip mall, all the while avoiding side-eyed glances from other patrons whom I was sure were judging me for my singledom. (They weren’t.)

Even though I survived my first solo date unscathed, I wish I had gone into it more prepared. If this is a new practice for you, I highly suggest you arm yourself with innocent but sometimes necessary distractions.

Like, If you’re planning a dinner or lunch date, take with you a book, a journal, craft, or crossword puzzle. That way, when you start to feel weird or you’re not sure where to look or what to do with your hands, take a deep breath. Reach into your bag. Pull out your distraction of choice and let out a sigh of relief. You got this, girl.

Pro Tip: An “activity” date is a great option for first-timers who don’t want to risk the awkward silences. Go to a matinee, visit an art gallery or museum, take a long walk in the park.

Whatever you do, resist the urge to pull out your cell phone. You know that feeling you get when you’re hanging with a gal-pal who’s been scrolling through Instagram the whole time, barely listening to your big news or latest updates? (It’s annoying, right?) If you’re willing to give your friends your focus why not do the same for yourself? You deserve your full attention.

3. Dress Accordingly

You know that old saying, “look good, feel good”? Well, it applies here.

Show up for yourself, babe. There’s something so beautiful and exciting about putting on some lipstick and your fave pair of shoes and hitting the town solo.

While I’m not suggesting you wear your prom dress from circa 2007, I am suggesting you treat this as seriously as you would any other date. While it can be tempting to throw your hair in a high pony, slip into some yoga pants and your favorite sweater — because it’s not like your date will mind, right? — I highly suggest you show up for yourself the same way you would show up for someone you’re trying to impress. Because really… who is more important than YOU?

4. Enjoy Yourself

Okay, so you’ve made it this far. You’re officially dating yourself. Take a deep breath. Stop worrying about who’s watching (it doesn’t matter), or what anyone else is thinking (nothing bad), or what the heck you’re supposed to do with your hands (whatever feels right).

Loosen up. Sit back and enjoy yourself. Try to pay attention to what you’re feeling. And remember, it’s okay to smile.

The point is to get to know yourself better.

The point is to feel at home and at peace in your own company.

The point is self-care, self-growth, and ultimately self-love.

5. Reflect

Congrats, babe! You survived your solo date. There’s nothing like a little reflection to put your feelings into perspective, learn from your experiences, and expand your consciousness.

I find journaling helps…

Here are a few prompts to consider:

  • How did you feel during your solo date?
  • Did you have any great epiphanies?
  • How did you find your own company?
  • Have you learned anything about yourself?
  • When were you the most uncomfortable? Why? What can you take away from that?
  • When were you the most comfortable? Why? What can you take away from that?
  • What would you do differently next time?

6. Plan Your Next Date

You didn’t think that was it, did you?

Get your next solo date on the calendar, ASAP. Make it a habit, and I promise you, in time it will get easier. More than that, you may find yourself craving solitude, peaceful moments with yourself, and the luxury of alone time.

This is a beautiful thing.

Because if you don’t love your own company, how can you expect someone else to?

Pro Tip: You don’t have to be single to date yourself. I’ve been in a relationship for going on 4 years now and I still take myself on solo dates all the time. Not only does it help me recharge my soul, but it makes me a better partner.

Pic via Instagram.

Confessions Of a Serial Dater

You know, the scariest part of leaving my little basement suite that very first day 10 years ago wasn’t the fact that I didn’t know my way around a new city, or the fact that I didn’t have any friends, or even the fact that I was alone. The scariest part was not knowing who I’d find when I finally got to where I was going. What version of myself would I be in that little pizza joint in the strip mall?

For so long I had built an identity based on my relationships with other people. I was a daughter. A big and little sister. I was a friend. A best friend. A teammate. An employee. I was the girl you might not have known that well in high school, but who would always smile at you in passing.

But who was I, really? Who was I a million miles away from all the things and people and places I had used to build my identity? Who was I in a place where I could literally be anyone?

Let me be clear: It’s not that I was trying to change or recreate myself. I was simply discovering myself.

I can’t promise you that once you get through the initial awkwardness of the ice-breaker stage, that dating yourself is going to be all rainbows and butterflies, and cute selfies. (Though, there definitely will be those things.) Like any long-term relationship, there will be challenges. You may fall in and out of love with yourself. Multiple times. You may have to fight for your love, adjust your priorities, and learn to accept your shortcomings. You may discover things you never knew about yourself (this is a gift, treat it as such, no matter the information). You may let yourself down. You may have to build yourself back up.

But hear me when I say this: The most important relationship you have is the one with yourself. The sooner you start honoring it, the better.

Looking for (self)love? Here are 14 fun, sexy, and spirited self-date ideas to get you started.

Originally published at

Littlefoolbook— true (& LOL-worthy) stories about growing up GIRL in a culture where beauty reigns supreme.

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