Emil Nolde, Wheat Field, 1900
Shortly after my friend’s long-term relationship ended, he met someone who made him feel all the things he wanted to feel. Almost instantly, he was sure about her; she, however, was not so certain about him. Or rather: she was sure she felt the connection, but her own life was complicated; she was contemplating getting back together with her ex, and besides, she wasn’t sure how serious of a partnership she was looking for, anyway. He felt desire, and a deep uncertainty that felt nearly unbearable at times while he waited to see if she would choose him.1
Around the same time, my other friend met a girl who he couldn’t get off his mind. She didn’t seem obviously interested in him, though they knew each other at parties and bumped into each other all the time. Eventually, he started explicitly trying to ask her to hang out one on one, and after one of these hangouts, they kissed. He wasn’t sure she was the right person for him—she had a very different relationship timeline and a more conservative lifestyle, but he was drawn to her sweetness, steadiness and sensitivity. Every time he saw her, he wanted very much wanted to see her again. Though she seemed initially unsure, she decided over the next couple of months that she really liked him.2
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If I had to describe the beginning of love, I would say: something is coming up that you just can’t ignore. It may be as a minor as a pea on the bottom of the mattress, but all of a sudden you’re not sleeping as well as you once were. Instead, you find yourself tossing and turning throughout the night. Something is troubling you. What?
Once you confront what’s troubling you, the complications may end. But more often than not, the uncertainty continues. The type of uncertainty is just different. Perhaps you are wondering if the two of you will start dating. Then you start dating, and you think, how long will we stay together? Or, should I move to Wisconsin to be with her? Or, how do I gently break it to her that I’m horribly allergic to her dog?
If you’re single, the number of people out there in the world that you could potentially date—the sheer illusion of optionality—can feel crushing instead of liberating. Falling in love whittles down the mass unknown to a radiant single figure. But anyone who’s been in a relationship for a prolonged period of time can attest that new uncertainties continue to pop up. No one, no matter how prescient, can predict all the challenges that will emerge over 20 years of loving someone. How many times have you heard, “Well, he was so different in the beginning, I couldn’t have known?” What one can know or reasonably guess is up for debate, but I don’t think anyone would claim that from any vantage point we can predict it all. Uncertainty is an inherent part of life.
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I’ve been meditating on this James Hollis quote a lot lately: “An ability to tolerate the anxiety generated by ambiguity is what allows us to respect, engage, and grow from our repeated, daily encounters with the essential mysteries of life. But the payoff goes even further. Certainty begets stagnation, but ambiguity pulls us deeper into life. Unchallenged conviction begets rigidity, which begets regression; but ambiguity opens us to discovery, complexity, and therefore growth. The health of our culture, and the magnitude of our personal journeys, require that we learn to tolerate ambiguity, in service to a larger life.”
I’ve always seen myself as a decisive person. Another way of saying that, of course, is that I’m a person who needs order to function, who always seeks to impose control over chaos. For most of my life, I saw uncertainty as something to be eliminated as quickly as possible. Last year, when I moved from New York to San Francisco, I was trying to resolve the open questions in my romantic relationship, and figure out if picking a city to live based purely on the resonance I felt with the people living there was a viable life strategy. I’ve now reached certainty on both counts, but of course new uncertainties have emerged in their place. In the past I’ve reluctantly accepted that new questions to answer are always coming up, but now I’m wondering what comes after reluctance: what would it feel like to exist joyfully alongside uncertainty, to treat it as something I don’t have to control?
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In work and life, I’m always experimenting. Take Bookbear Express: when I started writing this Substack four years ago, I had no idea it would become what it is. Which is to say, even now, I don’t know what it is.
Yesterday we had a meetup in Central Park. I was in a truly bedraggled state, having just returned from a beautiful wedding in the Catskills where I had no access to caffeine for 72 hours. But when I arrived and saw Justin, Annie, Terry and few others sitting cross-legged on a picnic blanket, I immediately knew I was going to have a great time. We were still going four hours later, having migrated from Sheep’s Meadow to a sports bar, when I had to run off for dinner. Everyone kept asking me if it was weird for me to be at a meetup for my blog, and I kept saying that it was… shockingly normal? Turns out, you can just start a Substack, and then people can subscribe to your Substack, and then you can meet them and really like them, and they can like each other. And also you can run a giant matchmaking experiment for hundreds of people at a time and some of them will actually start dating each other (there will be a post on this soon). And also you can facilitate workshops and hang out with people you met at the workshop you facilitated and then you can see them at the meetup for your blog and feel very happy.
Four years ago, I could not have predicted that all of this would happen. Even one year ago I couldn’t have predicted it! I probably would not have said I wanted it to happen if you asked me, since I’m quite shy and historically the idea of large groups, or even small groups, has been deeply intimidating to me. But having my blog evolve from me writing into the void to meeting people I like a lot and organizing various events centered around my most avid interests—relationships and feelings—has made my life so much the richer.
Uncertainty, when it’s good, can be so good. I have no idea where my work will take me next month or next year. Somehow that feels satisfying instead of scary.
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I don’t read tarot, and I don’t generally ask friends to read tarot for me. Perhaps this is superstitious, but I don’t wish to look too far into the future. Some lines from Alexander Chee’s essay The Querent that have always stuck with me: “I can say that love and money are what most of my querents wanted to know about, and I think those topics are all that most of us want to know about. Will I be loved, will the love last, is my lover cheating? Will I have money, will it last, will I be cheated? Will I get the new job, the new promotion? Will my book sell? It’s the shadow on every kiss and every dollar, that it might not be there tomorrow. If there’s a demon lurking when you read your cards, it is inside the querent when they ask about love or money. And it is inside you too, as you read.”
Like everyone else, I want to know. And also, increasingly, I’m learning that I don’t. Several years ago, I paid $15 to see a psychic with a friend in Toronto. She said two fairly specific things to me. Both came true. Maybe she was just a talented cold reader. At that point, what’s the difference? The passage of time since then has turned me into someone who asks questions grounded in the present.
I often worry that my uncertainty will lead to pain, either mine or someone else’s. I think that if I knew the future, I could prepare better for it, do all the right things, avoid mistakes. And yet other people’s mistakes often seem to me the most lovable parts of them. Because the person they are today is the one I got to meet in this universe, the only version that matters, and I treasure the real thing more than any could’ve been, any ghost.
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When you love someone, their beauty acquires a different kind of meaning. I often marvel that there are millions of attractive people in the world whose faces and bodies mean nothing to me, whom I can walk by, talk to, marvel at their build or dress or gaze without the impact of it ever seeping beyond the surface. It’s only when someone becomes truly precious that their appearance suddenly means something to you. Their freckles. Lower lip. Asymmetrical eyebrows. Bike tan. You stop appraising, start studying. You stop looking, keep finding.
I couldn’t describe your voice very well if I tried but I could recognize it anywhere, at any volume, in the middle of any sentence. It’s so dear to me. That means something, but what does it mean? Miriam, writing about Sally Rooney’s new novel Intermezzo, says that Rooney is working on her own theory of love. Intermezzo, if I had to sum it up in a sentence, is about how loves takes us places we don’t intend to go and can’t possibly foresee. Upsetting and unsettling places. Strange and warm places.
I always used to get mad at myself if I didn’t know. I’m still mad at myself for not knowing. But I’m trying to let it play out. A thought I’ve been experimenting with: if we stick uncertainty for long enough, the true shape of a thing is revealed to us. You just have to wait for the water to recede.
Rishi and I are doing another workshop in San Francisco on October 12th! As you might be able to guess from the title of the last two posts, this one is about resilience in the face of uncertainty. We’ll be exploring relationship uncertainty, work uncertainty, and… general life uncertainty. Workshops run from 10 AM to 5 PM with lots of breaks. We’ve only had 4 workshops to date but have had repeat attendees which I will take as a very good sign. Facilitating them has helped me enormously with the topics that we’ve explored (so far, friendship, rejection, conflict) and we’ve received lots of feedback that they’ve helped participants have the conversations they’ve been hoping to have in their own lives. People who attend tend to be people who are in a moment of confronting the topic at hand in their own lives, which makes the workshop feel particularly precious. All this to say: if this speaks to you, it probably speaks to you for good reason. And if it doesn’t, it doesn’t. Early bird tickets (first 8 people, in this case) are $275; we’re doing flexible pricing for regular tickets from $300-375. If you’re a student or just can’t afford the workshop, please email friendshipindustrialcomplex@gmail.com and we are happy to discuss options.
Note: For both this and future workshops, if you have a space for 15-18 people and are willing to offer it, email us. We will comp your participation as a show of gratitude!
They’re still dating.
They’re no longer dating.
It’s so strange and beautiful when something pops up on your phone and they are sentences and statements that you’ve been needing but haven’t received yet, and then there they are. Thank you for this xx
I needed this so, so much. Thank you!