Expat Dating Mom

When I first started dating again, I came across The School of Life on YouTube. One of their videos suggested an alternative approach to first-date conversations—a list of non-traditional questions designed to skip the awkward small talk.

Some of them required a level of stoic composure just to ask without bursting into a nervous giggle. But there I was, stepping back into the dating pool, realizing I had never actually “dated” the modern way: going out with dozens of strangers, interviewing candidates for the vacant “Love of My Life” position, only to likely never see them again.

Growing up, I was a fairly beautiful girl— allbeit nerdy, passionate about school, shy around guys unless I put them safely in the friend zone. My first serious boyfriend was actually one of my best friends. My initial impression of him was he’s not for me. He was popular and, I thought, a little vain—the total opposite of my dad. I figured he was impossible to impress and would never fall for me. When we eventually broke up, it destroyed my heart. Shortly after, when he found a new girlfriend, my sister remarked, “She’s so perfect for him, she’s amazing.” It stung, but I didn’t think she was being mean. I genuinely believed I didn’t deserve him, and that my sister was just stating the truth.

My sister was always eager to have the things I had, convincing me I didn’t deserve them so I’d hand them over: handmade crafts, friend groups, my confidence. The only two things she couldn’t take were my best friend and my slender frame—so she devalued and resented them instead.

Fast forward to four years ago: my ex-husband had moved out, the divorce was finalized, and I tentatively turned to dating websites. Back then, apps felt less algorithmically clinical, but swiping through minimal profile cards still felt entirely random. I preferred actual websites with long-form written pages. I wanted connection. I thought reading someone’s written words—their soul poured onto a screen—would help me understand who they were. (This was also back before Large Language Models could generate synthetic avatars to fool you.)

The School of Life teaches that finding love isn’t just luck; it’s a skill that requires self-knowledge and the courage to break old patterns. Alain de Botton recommends looking for traces of self-reflection in a partner, specifically an awareness of their own toxic traits. So, I wrote down a few of his recommended questions to test for self-awareness:

“What are you selfish about?”

“What would you go back and apologize to your parents for?”

Years later, I’ve forgotten most of them—proof I’ve given up on asking. But one stuck with me:

“How are you crazy?”

The responses to that last question were a wild spectrum:

“Nothing really special” (which, ironically, is the red flag telling you to run).

“I think I’m autistic” (disarmingly specific).

“Is this a joke?” followed by an intense eye-roll.

As it turns out, most people on dating apps aren’t primed for existential philosophy over a first drink. I am profoundly jealous of the people Alain de Botton goes out with. It sounds idyllic: well-articulated, sophisticated adults sharing their deepest vulnerabilities over a glass of wine against a backdrop of soft bistro jazz. They go home to rooms lined with bookshelves, share a plate of home-cooked Cacio e Pepe with a single basil leaf, pull off their cashmere sweaters, misplace their glasses, and stay up until dawn—not having sex, but exchanging detailed instruction manuals on how to handle each other’s emotional handicaps.

That was not my reality.

So, if anyone were to ask me the question, here is how I am crazy:

I was raised on gentle gaslighting. Maybe it’s an Eastern European upbringing, or maybe we’re all just constructed out of generational war trauma and forced optimism. But whenever I felt something was off as a child, the refrain was always: “No, you’re exaggerating. You’re just too sensitive.” Later, when my ex-husband hit me, my sister’s immediate response was: “What did you do to provoke him?”

Now, in relationships, I never truly know if I like someone or if I’m just waiting for the trap to spring. Whenever I brought a boyfriend home, my dad would ask, “Don’t you want to break up with him?” That simple question permanently tainted the joy of falling head over heels. It wired me to anticipate the other shoe dropping, to actively search for the hidden flaw until I inevitably find it.

Once I find it, I convince myself—and my friends—that this person is hideous, flawed, and impossible to live with. We break up because I suddenly turn cold, prickly, and mean. Then, a month later, the dust settles, and I realize that aborting another budding relationship wasn’t a necessary ejection of a bad partner—it was just my old pattern running its code again. The transplant didn’t take. But could it have?

And so, these days, I turn the question inward with a little more gentleness, and I ask: How are you, crazy?