Nice Guys Finish Last: Why the Wrong Men Seem So Right

We’ve all been there: you’re dating a wonderful guy who checks all the boxes. He’s thoughtful, sweet, and makes it obvious that he’s into you. On paper, he seems perfect. But something still feels.. off. Something is missing. Then there’s that other guy—the one who barely checks any of the boxes, yet there’s something about him. That je-ne-sais-quoi that makes you straighten up, fix your hair, and check your makeup the second he walks into the room. What’s going on here? It’s a common joke men love to make about women, but maybe there’s more truth to it than we’d like to admit: we don’t seem to know what we really want…

Take my friend, for example, who’s been dating a great guy from her office for a couple of months. It started with some innocent texts and banter, and then, after one notorious office outing things took a turn. After a couple of drinks, and perhaps one too many, he walked her to the train station where they said their goodbyes. Just as she was about to board her train, with a little boost of liquid courage, she called him.

“How far do you live from the train station?” she asked. Since then, they’ve been happily seeing each other—though still in secret. My anxious-avoidant friend isn’t ready to let anyone at the office know; that would make it all too real, and she’s not sure she’s ready for that. But here’s the thing: he’s a great guy. He loves her, cares about her, and makes time for her. And next to that they also have a great sex life going for them. What more could she ask for? Then again, we wouldn’t be women if we could just accept this great gift that landed in our laps and live happily ever after. No, there’s only one thing left to do: overthink.

If you’re anything like me, you probably have a mental checklist of what your ideal partner should be: smart, ambitious, funny, kind, successful, charming—and, let’s be honest, tall. And if you really let your imagination run wild the list doesn’t just end there. But by the time you’re done crafting your Mr. Perfect, your chances of success in the dating world are pretty much near zero. This unofficial study is based on many years of personal experience. But here’s the million-dollar question: is finding someone who checks off all the boxes the key to love, or is there something else at play?

Like my friend—whose name, like her relationship, I shall keep secret—I can’t help but wonder if there’s just one thing standing between us and our dream relationship: fear. Many of us, myself included, are guilty of it. We shy away from the guy who shows genuine affection and push away the great guy who makes his intentions clear. Instead, we yearn for the fantasy man we’ve created in our minds. Why? Because this idealized version can’t hurt us. In the realm of fantasy, we’re emotionally safe. We’ve all experienced heartbreak at some point, and those past wounds leave scars that remind us just how vulnerable we are. Since our brains are wired to protect us from pain, we create these checklists as a shield to keep anyone who might break our hearts at bay. This begs the question: are we really searching for love, or are we just trying to protect our hearts? After all, there’s only so much heartache a girl can take…

Lilé van der Weijden

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