How to Date Your Crazy

I should have known we wouldn’t work out when I messaged him one of my favorite quotes from Alain de Botton. It’s from the On Being podcast “The True Hard Work of Love and Relationships.” In it de Botton says the question we should really be asking on first dates is: “How are you crazy? I’m crazy like this?”

“I don’t get it,” he replied via WhatsApp. “How do you ask about crazy?”

Of course he didn’t listen to the podcast to find out.

I let it pass. He was sweet. He was cute. He was smart. He had his career together. I took this to mean he had his emotional life together too — all of it nicely bundled in a cultivated gift wrap and tied up with the sexy bow of an Australian accent. 

We matched on Tinder two days before he moved from New York to Colorado, and when we couldn’t work out a meeting before he left, I figured he’d disappear. But he didn’t. A month after we connected, he flew back to meet me. Despite my telling a friend, “It was fine, but I’m not sure I need to do that again”, five weeks later I found myself on a flight to his place for a three-day visit. 

It wasn’t a disaster from moment one, but it was close to it. His Australian accent couldn’t save us in a confined space where we were forced to navigate past our fantasies of each other to what was real. Under the shiny surface he was tense, immersed in acute anxiety — my attempts to accommodate him misunderstood and misconstrued. When I let him decide what suited his mood best—meeting his friend for a drink or seeing a movie—I was told I was indecisive. When I waited for him to finish showering after spin class before calling an Uber, I was snapped at, his body vibrating with the impatience that had permeated our hike the day before, and our lunch and shopping in Boulder, even though it was the weekend and we had nowhere pressing to be.

His phone became an escape hatch he slid down right in front of me, worshipping his Apple God throughout our final Sunday brunch. I ate my eggs silently, vowing I’d marry the succulent maple smoked bacon if it came in man form, and counted backwards through the hours till my flight would take off and me with it.


“I’m going to take a break from dating,” I told my friend Molly when I got back to New York, but two days later I signed up for Bumble, adding a new dating app to my Tinder/OKCupid mix, an addict doubling down on her drug of choice. I was hooked by the high of a potential connection.

Molly is a poet, recently divorced, and a freer spirit than me, by which I mean she’s been freer with her body in a way I envy, diving into dates with gusto, unafraid to make the most of the sex available to her. And yet, we’ve often ended up in the same place emotionally —- frustrated, dissatisfied, and disappointed. We’ve found men unable to take us seriously no matter how we’ve owned ourselves and our sexual agency.

Molly and I are forever swapping articles and poems and bits of novels, believing firmly in the way of writers that words can save us. Following one of her frustrating dating experiences, Molly sent me an “Ask Polly” column from The Cutthat answered a 44-year-old woman’s question, “Is agreeing to a casual relationship undignified?” And while Polly didn’t think so, she told the woman, “Step back and admit it: You are someone who can work with whatever you’re given, and sometimes that means you have a tendency to settle.”

Polly’s point was a deeper one. She made a metaphor about the woman being a luxurious banquet a man should want to linger over for a million and one meals; if he didn’t, he wasn’t worth the woman’s time. But I was stuck on the settling bit, my track record spottier there than I wanted to admit.

A few days later a man replied to my message on Bumble. “What’s that creepy thing on your dining table?” he wrote, referring to one of the pictures in my profile.

That “creepy thing” is a delicacy of Jinan, China. In the photo I am seated at a large round table on the evening of my brother’s wedding there, my new sister-in-law’s father beside me, an enormous sweet and sour fish plated before me. I am the guest of honor at this dinner, and as such I have first rights to every new dish laid on the table. This one is magnificent. A brown glazed beauty that curves up at both ends as if caught mid-leap. My smile is radiant as I lean toward it, chopsticks in hand. I am so happy to be with family, to be celebrating my brother’s love and commitment, to be on an adventure in a foreign land that my joy fairly pulses through the frame. 

I tried to explain all this to the Bumble guy but he didn’t reply, ghosting on me and proving Polly’s point: I shouldn’t engage with a man who doesn’t have my happiness on his menu.


Molly sent me another link, this time to the article, “The Central Paradox of Love,” that quotes renowned sex therapist Esther Perel on how to reconcile the ways intimacy and desire are at odds with one another. In it she states, “Not everything needs to be revealed. Everyone should cultivate a secret garden.” 

While not exactly what Perel means, I thought of how little I’d been cultivating my inner garden, how brittle the flower petals, how dry the seedbeds. I had indeed settled, my inner life becoming second to the swipe-message-meet-delete dating cycle, the desperate peaks and valleys of my drug. I’d sit on my couch, or up late in my bed, searching for distraction, for a stimulating story, for someone to spice things up rather than doing it myself. I was ignoring what I loved in search of love, which neither created nor attracted what I desired. 

It was time, I realized, to find my metaphorical spade. And so I did, digging, and digging, and digging some more till my life started to blossom again out of the fervent soil. 


“I’m really going to take a break from dating this time,” I told Molly, though I’m not sure either one of us believed me. 

My date the night before appeared promising till he opened his mouth. “I seem to be performing an act of dating abuse telling people my dating history,” he said, almost by way of greeting, and then proceeded to kick back a few beers and abuse me with his hot mess of a life story till I was slowing inching out the door, afraid his problems were an infectious disease I might catch.

I told Molly, “I have one more date lined up, and then I’m done.” 

My usual nerves were nonexistent when I walked into the bar. Why be nervous?I thought. I have nothing to lose. I’m going to be bored and dying to leave in an hour.I’d cut back on my dating apps, and dating time, but it still felt like too much. I preferred cultivating my inner life over sitting through a beer with another middle-aged man broken and bitter from his life not living up to what he had imagined it to be. 

But an hour later I wasn’t bored. I was laughing. A lot. He was cute, this guy, and Belgian. A consultant, he traveled all over the world without a permanent address. Some friends found this strange, but I got it. Why stay in one place when you could work from anywhere? Why be single and childless if you didn’t make the most of it? It was how I had been restructuring my life, cutting free of the ties of an office to spend a summer in the Pacific Northwest and a winter down south, working while I hiked and biked and met new people and explored the landscape. It was a relief not to be with a date who envied me, or asked for advice on how to become a consultant, or questioned the risks I took financially, but rather swapped stories with me of the pleasures and challenges of the life we’d chosen.

A few days later, after a pocket of silence that made me wonder if I’d read the signals wrong, he sent me a picture of a book I’d mentioned, newly bought off Amazon. “Thanks for the recommendation,” he said, “I can’t wait to read it,” and I thought, Oh, shit, this guy might really have my number.

And he does. He courted me with an old school style I found appealing, asking if it was okay to text me regularly while he traveled and booking time with me in advance when he’d be in town. He showed up with small gifts — a waterproof bag for my camera after I mentioned wishing I’d had one when kayaking; a box of dark chocolate-covered orange rinds, a favorite he didn’t yet know was a favorite but instinctually guessed right—surprising me with his quiet thoughtfulness. In everything he does and says I am made to feel that I am one of those million and one banquets Polly talked about. It’s been strange and surprising how easy it is.

While we haven’t outright asked each other “how are you crazy” or “does your crazy match mine,” we’ve been asking it of each other in subtle ways all along. From the minute I sat on the bar stool next to him and asked why he’d decided to become a consultant and travel the world. And the answer as our relationship builds and deepens, as it picks up steam and gathers inside jokes and references, keeps being yes. Yes, I am crazy like you. Yes, your crazy does match mine. Yes. And for now, as the true hard work begins, it’s more than enough. 

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4 Responses

  1. Marilyn

    This is lovely. Thanks for invoking a little hope (not for me, am happily married to a complimentary crazy), but for the world, I suppose. Dating can be hard. It’s nice you shared your joy, too. Thank you!

    • Ruth Gallogly
      Ruth Gallogly

      Thanks so much for reading, and for your kind words. It means a lot to me that you shared this.

  2. Jan Zahrly

    Delightful! I loved reading about how you are growing into the person you like and will be. And the guy sounds great. Your mother told me about this article – we are in the same book discussion group in Florida. I regret that you novel is “fantasy” – not my style but your writing is. peace, janz

    • Ruth Gallogly
      Ruth Gallogly

      So nice of you to read this, Jan. It means a lot to me that you liked the writing. My mom talks often about your book group, and how great the discussions are. I’ll have to drop in when down there sometime.


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