Isabel, Unhinged

Isabel, Unhinged

HOW TO SNAG A SECOND DATE (OR YOUR MONEY BACK!)

manipulative....or genius?

Isabel Timerman's avatar
Isabel Timerman
Sep 27, 2025
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I’ve been on a lot of first dates. Enough to qualify me as an expert (or maybe just a repeat offender). I know the choreography by now: the opening smile, the legs crossed under the table, the drink you finish wayyyy too quickly. The way you wait for the “let’s do it again” text the next morning like it’s a lab result that might change the course of your life.

First dates are absurdly high stakes for something so fragile. You either make it to round two, or you vanish: ghosted, erased. Twenty-five dollars wasted on an Uber. Sixty-five if you’re me and convinced a blowout is a non negotiable. All gone.

Most women unravel. Or at least I did. I fumbled men I could have been with forever if I’d just dimmed the lights on myself. And I know, I know…there’s romance in the idea that someone should love you at full volume. But let’s be real: dating is a game. And if you don’t learn the rules, you don’t get to keep playing.

That’s where my rules come in. These aren’t the generic “order the pasta, not the salad” tips you scroll past on TikTok. They’re strategies I learned the hard way—trial, error, and humiliation. I made the mistakes so you don’t have to. And when I’ve used them? The man across from me didn’t just like me. He fell. Hard. Did the relationships last? Maybe not. But that’s not the point. The point is being seen as desirable and chosen, not disposable. The point is making it past that first date, into something resembling possibility. Let’s begin!

Sweater Theory

A friend of mine who makes men fall in love like it’s a party trick gave me this rule: wear a sweater on the first date. Not a corset. Not the smoky eye you save for your least favorite ex’s funeral. A sweater. Why? Because sweaters trick men. They register as “safe,” “sweet,” “approachable.” They think you’re the girl who bakes banana bread and answers texts on time. Meanwhile, under that turtleneck is someone who will ruin their life. The contrast destabilizes them.

No Phone

If you happen to arrive first (which, ideally, you shouldn’t), don’t sit there scrolling. Look up. Look around. Act like you belong. The rule stands for the whole date: no phone. Not on the table, not in your hand, not flashing notifications. As far as he knows, you don’t even own one.

The Echo Effect

Mirror a phrase he uses…just once. If he says “that’s insane,” drop “insane” into your next sentence. He’ll feel understood without realizing why.

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