The case for taking yourself on a solo date—no matter your relationship status


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Photo: Getty Images/ Elitsa Deykova

The crisp air of a New York City autumn screamed romance. I could feel it on the sliver of exposed skin between my tight black turtleneck dress and black suede boots while I passed leaves in hues of orange and yellow. I strolled past the famed Dakota building on Central Park West, the fluted intro of “Strawberry Fields Forever” serenading me from inside Central Park. I was with my perfect New York date, who happens to be…um, me, Mary Grace.

It amazes me that amid a with “Thank U, Next” and “Truth Hurts” topping charts, we have yet to talk about how mastering the solo date is step one in learning how to be happy alone. If you find yourself unexpectedly single, there might be this drive to go bold and book a solo trip. And, if you can swing it, that’s a great option. But, if you find yourself unexpectedly single and also broke, the solo date can serves as a small-scale version of a fulfilling adventure that can help you learn how to be happy alone.

First, how do go about taking myself on a date?

The design and rules are simple: Think about what you’d love to do on a Perfect Date—whether that includes things you’ve never done before or tried-and-true activities you really love. For me, a great-date format is Central Park in the fall, spending an hour meandering through the Metropolitan Museum of Art’s most decorative rooms, and then having Italian food. Maybe you want something that looks less like a blatant montage of a Nora Ephron movie—I don’t know your life.

The key here—whether on a solo or partnered date—is having an experience that leaves you feeling fulfilled. And according to travel coach Dylan Grace Essertier, the same component that makes a solo trip fulfilling makes a solo dat fulfilling: intention. “Consider the difference between nervously sitting alone at a restaurant, wondering what people might think of you versus saying to yourself, ‘how great is it that I can be my own best company?'” says Essertier. “This mental reframe will really help you enjoy the present moment, embrace taking things at your own speed, and soak up the joy that comes with being 100 percent in charge of deciding how to spend your time.”

Nervous about your first try at the solo date? Start slow by eating at a local restaurant. “Often I suggest my clients start with a shorter solo trip closer to home so they can gauge how it feels to travel alone before booking that one-way ticket to Bali.”

If you’re solo dating, do you need to be exclusive? With yourself?

“What if I want to be open to the possibility of a relationship?” you may be asking. “Must I stay self-partnered forever?!?”

To be clear, a solo date isn’t a rejection of love, intimacy, or dating as a whole. Rather, it’s really just an opportunity to feel secure and confident with yourself. Since self-esteem and strong relationships go hand-in-hand, that’s only going help form healthy dating habits moving forward.

Who says you can’t take yourself on a solo date, even if you’re not single? “Single” is a relationship status. “Solo” is choosing to embrace the adventure of solitude.

“Enjoying dating yourself can help you to not feel desperate to make imperfect relationships with others work out,” says psychotherapist and sexologist Laurel Steinberg, PhD. “You can have an ‘if it works out, great, but if not, great, too’ attitude, and not act clingy toward people who don’t treat you in the ways you enjoy being treated. Once you know how to be great company to yourself, you never again have to fear being single or broken up with.”

And, hot take: Who says you can’t take yourself on a solo date, even if you are in a serious and established relationship? “Single” is a relationship status. “Solo” is choosing to embrace the adventure of solitude.

What I’ve taken from my pursuit of learning how to be happy alone

In short, I’m loving myself more than I have in years. I’m having so much fun and enjoying the moment I’m in. Through solo dating, I’ve gotten to observe all shades and nuances of myself, completely uncolored by the influence of another person.

And, to be clear, I love love. But at this point, I refuse to put my life on hold for Mr. Theoretical Nebulous Someone Someday. Life passes you by if you wait around for other people, and I intend to enjoy my time as much as possible.

And yet, learning to be happy alone doesn’t happen overnight. So, in the interest of being completely forthcoming and honest…

On a recent solo date, I was feeling particularly down. I took myself to a fancy holiday-themed bar for an overpriced martini. I ate my Italian dinner thoughtfully and silently. I trudged home in the rain, very aware that it’s Just Me now. But I don’t like seeing my date (me) sad, and exercising that bit of self-compassion allowed me to start again fresh and re-centered in the morning.

Solo dating or not, and partnered or not, you will have days when you feel like you’re not enough. What matters is that you continue to work on the one relationship you’re guaranteed to have for the rest of your life: the one you have with yourself.

Still need some support? I got you, babe. Here’s a pros top tips on how to be happy single, even if you really really want an S.O. And knowing your love language can help you communicate better with yourself. 

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