On this Valentine’s Day and every day: how to date yourself

We make the effort with other people. Why shouldn’t we do the same for ourselves?

I’ve been planning it for a week. There will be a blanket, a bottle of wine, cheese and charcuterie — the makings of a romantic picnic under the almond trees of my favorite park, and none of the typical distractions to keep me from spending quiet, quality time with the person I’ve become so loyal to over the years:


I’m as single as one gets, and yet as Valentine’s Day approaches, I’m looking forward to it. Rather than a day for resentment or loneliness, I see it as another good opportunity to celebrate my strongest, most important relationship. The one I have with lil ‘ol me.

It’s an idea I’ve become very passionate about over the last decade and a half, extending far beyond Valentine’s Day.

At 19, when I moved from North Carolina to Boston — the first of many places I’d trek to where I knew no one — I first began to understand what that meant.

In the heart of Massachusetts, I found there were a lot of things I wanted to do, a lot of places I wanted to go, and not yet having a circle of friends forced me into two choices:

Wait, or do them by myself.

The more I chose the latter, the more I realized how much I enjoyed it. I would check out new restaurants and museums, have solo picnics on the Esplanade, take day trips around New England, to beaches, to fish shacks I’d read about, to little towns just to walk around. In those years before the explosion of smart phones, I’d bring a camera, and a book or newspaper and relish the time to simply think and and read and watch — seeing things I never noticed when I was with someone else.

I was smitten. I started dating myself then, and never stopped.

Over the years — moving around a lot, traveling solo for work and traveling solo for fun — a solo date became something I actually craved and sought out, even when I was in a relationship with someone else. I have incredibly happy memories of traveling and relocating alone, especially early on, because I see it as an act of bravery and self optimism at that young age, and because I think it made me who I am.

I would trek often to New York, using the time to linger in cafes, to walk through neighborhoods I didn’t know, to happen upon used bookstores and tiny music venues I never knew — titles and songs that were suddenly my own, rather than mine to share with someone else. I discovered that I adored going to restaurants alone — sitting at the bar and treating myself to a fine dinner and a glass of wine with only me and my thoughts, my reading material, the vibrant buzz of the place all around me. I started traveling around the country more, and through those experiences I realized that working through the awkwardness and the fear of judgment of doing certain things alone, I came out feeling empowered.

I remember a specific night, while traveling to Columbus, Ohio for work, when I went to a cocktail bar on a packed Friday night when there were no seats available and I had to stand around with my drink, all by myself — quite a different thing than sitting at a bar with a book. I really wanted to experience it, so I stayed. When I left, I thought “If I can do this and be comfortable, I can do anything.” It gave me a sense that I knew myself more than I had when I’d entered, and that by taking myself on this date, I’d challenged and pushed and inspired myself toward growth.

And isn’t that everything we hope for in the best of our relationships?

I tried to nurture that growth, through solo overseas trips, through making the most of my company time on the road. I walked through markets alone, went on boat trips alone, hiked alone, took in sunsets alone, enjoyed happy hours alone. In addition to finding that spending time by myself actually granted me new friendships I never found and conversations I never had when arriving with another person, I came to understand that spending quality time with myself, and appreciating myself was extremely satisfying. After all: our relationship with ourselves is the only one that will see us through every decision, failure and victory; it’s the one relationship we’ll have, for certain, forever. We should all take the time — to be kind to ourselves, to enjoy life on our own terms, and to never wait for someone else to do what we really want to do.

Five ways to date yourself on Valentine’s Day, and any day:

Give yourself a gift. Present can feel nice, especially if they’re coming from someone who knows you well enough to understand exactly what you want or need. That’s you! So go ahead, splurge a little — on flowers, on chocolate, on a new book, something for the kitchen, a special bottle of whiskey or wine, or what the hell, if you’ve got that $$, something bigger. You’d probably make that effort if you were in a relationship with someone else. Why wouldn’t you for yourself? I’m getting myself a fresh new notebook and a nice gel pen.

Say kind things to yourself. This might be the biggest challenge for a lot of us. I know it is for me. While I try very hard to be kind to others, I can be incredibly mean to myself — criticizing my appearance, my interactions and especially, when it comes to accomplishments, production and work, telling myself I’m not enough. Because of those instincts, I think that one of the kindest, most loving things we can do for ourselves is to decide to give ourselves a break, to look beyond our failures and our flaws and celebrate the best of us. This year for Valentine’s Day, I’m determining 10 things I love about myself, writing them on post-it notes and putting them around my apartment. Every time I see one I will repeat it to myself, and remember to believe it.

Have a romantic evening (or afternoon, whatever you got). Plan it like you would a special date with anyone else. Maybe it’s a nice dinner, a sunset stroll, fancy cocktails, a new museum, movie or show, or an elaborate meal at home with something special to drink, an appetizer or ingredients you might not normally use. I’m taking my aforementioned picnic in a park, splurging for things I wouldn’t normally. I’m bringing my camera and a book, of course.

Focus on actively savoring the moment. One of the curses of humanity is we so rarely bask in a moment; often that we only realize how great things were upon looking back. The wonderful thing about being alone is the ability to truly take in an atmosphere. Take a look at the world around you. Drink in the details — the tastes, the textures, where the sun is sitting in the sky. Think about how you feel right this moment, and try to lock that away.

Document it.  You took the time and the effort to take care of yourself, to enjoy your own company, to celebrate in the things you enjoy and the person you are — and that is beautiful. What an act of self-optimism indeed. So take a photo of your labor of self love; I bet you’ll look back later and smile.

12 thoughts on “On this Valentine’s Day and every day: how to date yourself

  1. Wow. I feel the exact same way. I’m happily married but I love to explore new places solo as well just to really tune in.

  2. I love this Amelia!! I’ve told you before, traveling afar by myself is scary for me. I’m afraid. But: I love spending time by myself, eating, drinking, reading, thinking. I don’t do enough of it. I also probably don’t love myself enough; or, maybe more accurately, appreciate myself enough. I don’t insist she (me) gets a fine meal with wine, a nice gift, time for herself. Thank you for reminding me!! Happy Valentine’s Day!!

    1. Love this! Thank you for sharing your thoughts and your personal journey with all of us. And most of all – Happy Valentines Day Amelia! 💖💖💖💖💖💖💖💖💖💖💖💖💖💖💖💖💖💖

  3. ” To enjoy life on our own terms, and to never wait for someone else to do what we really want to do..” Me encanto esta parte. Gracias chica por tus palabras y ayudarme a ordenar mi cabeza de nuevo.

  4. I started going to Tuesday night movies at the local theatre, by myself. My husband has some health issues and doesn’t care to go on a work night. I kind of enjoy going by myself.

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