Leo's Lemonade

Leo's Lemonade

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Leo's Lemonade
Leo's Lemonade
Go on a solo date!
Wisdom for Winners

Go on a solo date!

Wisdom from Ako

Leo Ariel's avatar
Leo Ariel
Feb 14, 2025
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Go on a solo date!
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Cross-post from Leo's Lemonade
Hello to all the lovers out there! Today, I'm sharing a conversation I had with fellow writer, Leo Ariel. Leo and I both write about seeking wisdom — sometimes knowledge— for a better life. We come at it from different angles. I appreciate his ravenous sense of curiosity. Follow Leo and you can find out more about what he's currently reading, his insights from learning how to dance, or what he's learned over the course of twelve months in twelve countries. In this interview, we talk about dates. Not with your most recent match, but the one you've been matched to the longest-- yourself. Find out the joys of taking yourself on a date, how to do it, and what just might ensue. Enjoy! -
Akiko Mega

My guest today is Ako. She is irrationally obsessed with understanding how we show up in the world as our truest / most unapologetic selves. She’s influenced by her studies in the yogic tradition, her time in Bali, a daily meditation walking Shadow, her (imaginary) dog, and Tinder as a spiritual practice. She spent her earning years being a kickass fashionista designing the retail and customer experience at Maison Margiela, and now she helps rich and powerful people be less of an a—hole.

Here is my illuminating interview with the one and only:


LEO

IF— You can write 1 magic email that all young people receive. Inside that email is a CTA (call-to-action). Unlike all other SPAM emails, this one the recipient will execute the action. What would the CTA be?

AKO

Take yourself on a solo date like someone you’re really, really into!

Isn't it ironic we spend time, energy, and money on someone we don’t know before we spend it on ourselves?

LEO

Go on...

AKO

The solo date. This is a practice based on Julia Cameron’s Artist Date. The idea is to take yourself out. Out on a date, and out of your routine. Sometimes out of your comfort zone. It’s an intentional way to be with, and get to know yourself.

In the process, be curious about yourself as much as you would a cute date. (You ARE a cute date!) Be attentive. Follow your excitement, your curiosity, your thought process. Notice what excites you. Let that guide you to the next thing that excites you and see where it brings you.

LEO

Can you share an example?

AKO

About a year ago, I took myself on a hiking date. I’d moved to a city with mountains and parks with hiking trails– it was part of the draw to moving here– and yet I hadn’t been on as many hikes as I wanted. So I asked myself out.

We – that’s me and myself!-- chose an easy trail in the middle of the city with a panoramic view of the city at the top. We had great conversation on the way up and had such a great time, I found myself not wanting to go home. So I asked:

“I had such a great time. If you have time, would you want to continue on for a coffee?”

I laughed at myself because I felt shy asking myself out, just like I might an actual date! I noticed I had plenty of time before my next plans, so I agreed! We went to a cafe I’d bookmarked a couple of weeks ago and continued to get to know each other over sandwiches and coffee. It was one of the best dates I’d been on in a really long time!

Why? It wasn’t the hike or the coffee. I felt really seen and heard. If we can't or won’t offer that to ourselves, how can we ever expect to receive it from anyone else?

It sounds weird, but trust me. You need to take yourself out.

LEO

Are you like... talking to yourself out loud?

AKO

I play both parts, kind of like in skits in an Instagram reel.

Do I do this out loud or silently? To be honest, I’m not sure!! (laughing)

I do Q and A it, as if I’m dictating what I’m seeing playing in a film. I continue this two-way conversation all the way through until after the date.

     Me as the asker-outer: “So I noticed you’re really into art and design.”

     Me as the potential date: “Yes, I am! But I haven’t been out to see many shows recently”

     Asker-outer: “Have you seen the Ryuichi Sakamoto show? I’ve been wanting to see it, but have been looking for someone to go with– I love a post-show coffee to talk about and process everything I’ve seen. Would you be interested in going?”

     Potential date: “Sure! When should we go?”

LEO

How often do you do one?

AKO

While Julia Cameron suggests a date once a week, work out what is a good pace for you. Just like in a real dating situation. You figure out what is a good cadence. There is no right answer. what works for you.

I once heard an older wise woman offer advice to her son when he was a newlywed: “Have date nights at least once every two weeks. Go away for a weekend every two months. Go on a special, big holiday every two years.” This cadence seems to work for me.

LEO

Any last words?

AKO

Take yourself out! Have fun! Some important points: don’t tack it on to an errand, or work (you wouldn’t do that to a potential date, right? Then don’t do it to yourself.) No bringing a second wheel on your date! (You wouldn’t do this, either, right? Though a friend recently told me she brought a friend to a first date…!)

It sounds a bit woowoo, but trust me on this: the world needs you to be fulfilled, kind, and the best cheerleader to yourself.

Get to know yourself. So go on a date. Fall in love. With you.

Photos from Ako's datesPhotos from Ako's datesPhotos from Ako's dates
Photos from Ako's datesPhotos from Ako's datesPhotos from Ako's dates
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Go on a solo date!
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