Your Appointments for a Date With Yourself
Because the art of romanticizing your life deserves a place in your calendar.
I stumbled into the art of dating myself in a season that was anything but romantic.
When my husband, Carter, was diagnosed with leukemia, life contracted overnight. In the earliest days of his treatment, he still wanted to attend a bachelor party at Sea Island in an effort to reclaim the normalacy of life as a twenty-seven year old guy. By doctor’s orders, I went along, not as a guest, but as a caregiver on quiet standby. I remember feeling acutely aware of myself: alone at dinners with the company of only a novel; solo poolside, convinced everyone must be staring and wondering who was this strange woman haunting the property.
On the last evening of the stay, I wandered down to lawn chairs to watch the sunset, wrapped in that particular loneliness that hums just beneath the surface. Then, a gaggle of chic young girls approached me and asked, quite earnestly, what my story was — and where I was from — because I “seemed so glamorous being here all alone.” They told me they’d been playing a game all weekend of “Who could she be?”. My favorite guess of theirs? A literary agent from Chelsea, London.
I laughed. I glowed. I blushed. And I realized something subtle but seismic: no one was pitying me. No one thought I was strange. I was simply . . . a woman at a beautiful place, alone.
Later, when Carter became neutropenic throughout his treatment and our world narrowed even further, my only sanctioned outings were solo dinners — hospital cafeterias, quiet restaurants near treatment centers, the occasional bar seat around town. At first they felt heavy. Then they felt strengthening. I learned how to order confidently. How to savor slowly. How to sit without reaching for my phone like a flotation device.
Some nights I made fascinating friends, bellied up at the bar. Other nights I disappeared into a book so fully the room dissolved around me. In those dim, in-between hours, I found a surprising amount of peace.
Carter is healthy now, and life is so wide again. But the habit stayed!
These days, I never go to New York City without a standing date for one at Bergdorf Goodman, tucked above Fifth Avenue, where champagne feels like punctuation and dessert is a foregone conclusion. I also adore carving out a special reset, just for me, at a favorite local coffee shop on a slow, meandering morning.
Here is what I know now: No one is going to romanticize your life for you. Not consistently. Not with the specificity you deserve. That work belongs to you.
To sit alone at a candlelit table — or in the bright gloss of a French café — in crisp denim and a collared shirt, lashes darkened, lips softened with balm, a novel tucked beside your glass? That is not loneliness. That is fluency. Fluency in pleasure. In pacing. In self-possession.
We so often romanticize being chosen. This is about choosing.
Below is your checklist. In order. Consider it an appointment with the most enduring companion you will ever have.
Your Appointments for a Date With Yourself
1. Set the Scene Before You Leave
Decide your mood as you settle in to make a reservation and guard this date on your calendar as a non-negotiable. A dark, candlelit corner with low jazz and tiny votives flickering against brick? Or perhaps a bright, French café moment with bistro chairs, clinking cups, and buttery light?
Text no one. Tell no one. This is yours and yours alone.
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2. Get Dressed Like You’re Seeing and Being Seen
It doesn’t need to be uncomfortable or stiff: Crisp jeans. A proper collared shirt. Sleeves pushed just so.
For the face? Mascara. Eyeliner. Brows brushed up. A balm that makes you look like you drink water and mind your business. No foundation: Let your skin breathe.
Optional but encouraged: a spritz of an expensive-feeling scent.
I highly encourage turning on a feel-good playlist and elevating a tiny detail: press your top; buff your nails; clean your rings.
Extra-credit if you wash and iron your sheets before you leave, so the coziest, most crisp bedding is waiting for you to slip into after.
3. Pack Your Companions
Pack a tote with a few glossy magazines or a fizzy novel.
4. Arrive Early
If you can, walk to your date, or ask to be dropped off a few blocks away. Arrive slightly flushed from fresh air.
Before checking in with the hostess, glide over to the bar for a welcome cocktail. Don’t pull out your reading companions quite yet; stay full present. Enjoy eye-level conversation and observe the the choreography of bartenders as they alchemize.
When the time for your reservation arrives, introduce yourself with a steady voice; shoulders back. Settle in, phone turned off, and take in the room around you.
Engage and connect with your waiter, and invite them to guide you through the evening. “What’s your favorite thing on the menu?”
5. Your Ceremony of Events
If it’s daytime: Sparkling Water + Coffee → Soda or a Mocktail.
If it’s evening: Cocktail → Wine → Champagne.
6. Order Something Slightly Indulgent
I highly recommend selecting a specialty or inviting the kitchen to use their imagination, depending on your culinary setting. At the very least, try something seasonal and off your typical menu.
7. Read Between Bites
Alternate your sips and pages. Underline something and let yourself linger. There is no need to rush. In fact, try to slow down the time.
8. Dessert, Always
Regardless of hour: you will be ordering dessert. This is not optional. Take this course as an opportunity to notice and name sensory details enveloping you. The weight of the glass. The way candlelight flickers against wallpaper. The sound of forks against china.
9. A Romantic Exit
After you’ve taken your final bite, pay the check and finish your libation. Conclud the chapter or article your on. Then, on your egress, make eye-contact with your waitstaff and hosts and thank them generously.
10. An Additional Ritual
For a Morning Date
Afterward, pop into a specialty store and buy a bouquet. Trim the stems properly when you get home. Choose one more true little luxury (under $25). A French soap. A beautiful piece of stationery. A candle. Something unnecessary and lovely.
For an Evening Date
During the break between your entrée and dessert — and only once — pull out your phone. Scroll Etsy and order one small treat (under $25). A linen tea towel. A hand soap. A tiny treasure for future you. Write a note to yourself in the gift message box.
11. A Grand Finale
Change into something soft. Light a candle and turn on a soundbath or meditation.
Journal one page about how it felt to love yourself seriously.
This article has me thinking I need to take myself on a date more often! I used to do this right after I graduated college and loved it. Savor savor savor 🥂