How To Be Your Own Best Date

March 26, 2019

How to Be Your Own Best Date I wit & whimsy

When I was studying abroad in Paris I became accustomed to plenty of free time by myself and, as someone who loves to set out and explore new places, this meant partaking in plenty of activities solo, including dining alone. Thanks to Parisian cafe culture, I was able to get used to eating and drinking at a table or bar solo. It’s a practice I still to this day enjoy from time to time and particularly when I travel alone.

How to Be Your Own Best Date I wit & whimsy

How to Be Your Own Best Date I wit & whimsy

How to Be Your Own Best Date I wit & whimsy

How to Be Your Own Best Date I wit & whimsy

How to Be Your Own Best Date I wit & whimsy

So many people I know are paralyzed by the idea of dining solo or doing activities solo. Mostly for fear of what other people think. But living in New York I’ve come to realize that I’m not always able to take advantage of all the city has to offer with someone else with me. What’s more? Sometimes I want to do things alone! I’m extremely social by nature, but I also treasure the time I spend alone.

One of my absolute favorite memories of living in New York was in May 2017 when I went to the New York Philarmonic’s performance of Breakfast at Tiffany’s. (The band plays along with the musical scenes as the movie plays). I was just back from nearly two weeks in France and coming up on celebrating nearly one year in business for myself. I got all dressed up and headed up to Lincoln Center – feeling as though I was on the best date ever – one with my beloved New York City. As I approached Will Call to pick up my ticket the woman behind the window remarked “Here all by yourself?” And I replied “I’m on a date night with New York City.” She smiled and giggled and then said, “If I had a cute single boy to seat next to you, know that I would.” I loved the genuine sincerity of her words and I’ll never forget that moment. It wouldn’t have happened if I hadn’t been there alone.

I understand that being out in the world alone – particularly at restaurants when you’re surrounded by people socializing – is like exercising a muscle you didn’t even know you had but I can’t say enough good things about it. Some of my most wonderful travel memories have come from conversations with the bartenders and people that I meet when dining solo. And here in New York I am trying to do more of this. Some of my best ideas often come when I give myself the space to just think and breathe and see what’s going on in my city. I allow myself the room to just walk and see where I go, to see a new spot I’ve been wanting to check out or to find a refreshing environment in which to read a book.

If you’re interested in getting more comfortable with the idea, I suggest first doing a solo museum date or a walk in your favorite neighborhood park. Work up to that dining alone experience. Perhaps get a quick drink at a bar you like or at a hotel nearby where plenty of people mingle. And remember to really step back and experience the experience. I highly recommend airplane mode on your phone as you set out to try and be your own best date. The experience isn’t the same if you spend the whole time looking at your phone. Be present with yourself just the way you would if you had someone opposite you.

While I love my friends and my network, I always want to continue to remember the joy in stepping out your door and enjoying your own company. It’s a refreshing way to get back to hearing yourself.

And p.s. for my fellow New Yorkers, I love that The Infatuation recently published an article on where the best bars are for a solo burger. They really understand this burger-loving gal!

Lace Dress via Rent the Runway (wearing an 8) // Alice + Olivia Shoes // Gucci Bag

p.s. thoughts on being single andย what eight years in NYC has taught me.

[Carter Fish Photography]

what I'm wearing

16 comments on “How To Be Your Own Best Date”

  1. For the past few years, I’ve always taken myself out on a Friday evening date. This used to be a glass of wine and an order of patatas bravas at my neighborhood tapas place, but has since morphed into a bookstore visit + cupcake/cocoa run, or taking myself to a movie that Sri has zero desire to see. With the baby fast approaching, I’ve shifted gears and bought a Wednesday matinee ticket for all the plays and shows I want to see before the baby arrives. CHERISHING the time you have with yourself is such a luxury, and one that we take for granted.

    1. I remember you telling me about this practice and absolutely love you for doing it! Itโ€™s so important to cherish that solo time and glad you do so! Love the idea of weekday matinees too! Going to do that on a future solo date of my own!

  2. I love being by myself JUST as much as I do with other people. Especially if it’s something I know I’ll love (like a movie or event) that I don’t know how a friend would like it…. I want to savor it just for myself and not subject it to someone else’s preferences/judgments lol ?

  3. thanks for this post! I have been working on feeling more comfortable going out and about and exploring NYC by myself, and this post helps keep up that momentum. Just last week, I took myself out for dinner at the new momofuku noodle bar in columbus circle and absolutely had a blast sitting by myself at the bar, chatting to the other solo diners at the bar (who were so friendly!). It was truly a moment of “I should do this more!”

    1. Yay! So glad you enjoyed it and good for you for getting out there! I haven’t been to Momofuku in so long and now you’ve inspired me to make that a solo dining spot for myself in the near future. Isn’t it so nice when there are other solo diners to chat with!? I love it!

  4. Love this post and I feel the same way! Itโ€™s so great to travel alone and feel completely comfortable doing things solo but I have yet to reach the point of dining alone in NYC. After this post I think Iโ€™ll make it a goal to do in the next two months!

  5. Co-sign so much of this! I still remember the first time I took myself to The Met and dinner + a drink a the bar after – it was forced at the time because all of my friends were out of town on this one particular weekend but ended up being the best. A newer favorite ritual is having an indulgent breakfast by myself on a Saturday morning, either with a podcast or a book. Truly the best!

  6. Love this post. I get so many weird looks from people when I mention I’ve gone tons of places alone, but why shouldn’t we? Why should I limit myself to not going somewhere I want to if I happened to not have anyone to go with? And as you said, in fact sometimes I want to go alone and just be alone with my thoughts, to experience new things, and to have peace with myself. Sad for those people that miss out because they are afraid.

    1. Some people really are paralyzed by the idea but they need to learn to let go a bit more I think ๐Ÿ™‚ I am so glad you’re not one of them and that you see the value in spending time with yourself!

  7. This is such a fantastic article! I travel for work rather frequently, and I’ve come to look forward to those nights that I get to hang out with myself. It’s such a nice treat. On a totally unrelated note, your complexion is amazing! You look so beautiful in these photos ๐Ÿ™‚

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