Recovering

Recovering

The long game of boundaries

On why you can't stop abandoning yourself

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Holly Whitaker
Dec 28, 2025
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The Long Game of Boundaries

May 2021

In my mid-thirties I met up with a guy from Tinder while extended vacationing in Italy. We’d matched that day, the conversation had been fun and easy and charming and it was a no brainer whether to meet him corporeally. By then I’d discovered my tendency to lower my standards for company while abroad to soften my loneliness. With him, at least from our initial conversations, it appeared I could keep them.

We met in a piazza where he looked so different from his profile that I ducked him when he approached me directly and familiarly, believing he was one of the hundreds or thousands or hundreds of thousands of Italian men that are under the impression American women swoon at their unsubtle misogynistic overtures; kissing noises and fast advances and hands on you before you can remember that No in Italian is No. We walked past each other, sent a few more messages on Tinder, and minutes later realized yes, that was me and that was him and let’s meet at the fountain in the middle. When he told me he was thirsty and we should find a drink, my sober-pickled mind walked mechanically to a mini grocery to buy a liter of water. Looking for a drink, by that time in life, was looking for mineral water stored in single-use plastic. When we got to the threshold of the store and I asked if he wanted sparkling or still, he laughed, said No, a drink, like wine. I said Oh, right, of course, I don’t drink but yes we can sit somewhere. This was before I learned to avoid such situations by explicitly stating I am teetotal in my dating profile, a descriptor still missed by most even though it is now prominently advertised.

He was struck by my abstinence, intrigued, and he ordered two quartini of terrible Chianti (I assume because of the location of the restaurant and the price they were terrible though I have no real way of knowing that) while he spent the rest of the night discussing whether or not he had a drinking problem. He was vexed, working out a possible addiction against my unicorn of abstinence, and I was tired by the end of the night, but then recall at the beginning when I told you: Sometimes we lower our standards when traveling, compelled by the simple ache for companionship.


“Maya Angelou begged us: When someone shows you who they are believe them the first time. And I find that it generally takes me a total of ten showings to believe.”


I was not attracted to him at all, at first. When I took him later that night to show him where Caesar was really murdered, and he asked if I was trying to seduce him, I was genuinely surprised because my demeanor screamed No thanks. But then again, my history has shown men are mostly attracted to indifference at worst and repulsion at best and never to what feels mutual.

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