Dear Level

5 Habits of Highly Insecure Men That Women Hate

We all have moments where we lack confidence—but that’s no free pass to be a creep

Elisabeth Ovesen | NYT Bestselling Author
Published in
5 min readSep 10, 2021


I recently found myself in a cringeworthy virtual conversation with Jacob, a film producer who gives off some powerful #MeToo vibes. I don’t speak with this guy often, but when I do, it’s always alarming. He’s usually tipsy or full-blown drunk. With each sip, he loses more of his composure and is less able to hide his true intentions.

“You’re so smart,” he slurred.

“You’re dynamic. Do you know that?” he continued. “And you’re gorgeous. A powerhouse. None of the men you’ve ever been with know how to handle you. I mean, do you know how beautiful you are?”

His compliments flowed unedited, one after another, in a conversationally unnatural manner. On the surface, they may seem flattering, but each show of praise was a thinly veiled attempt to disarm me.

“You’re absolutely right,” I responded to his rant. “I’m all of those things and more. Thank you for seeing me exactly as I am.”

“Whoa!” he said. “Be humble!”

“Be humble? So, you can compliment me, but I can’t compliment myself. I can’t see myself as I am, but I can see myself through your eyes?”

“Exactly — I don’t want to hear your shit,” Jacob replied with a chuckle, trying to pass his insecure misogyny as a joke.

I don’t play that way.

My conversation with Jacob lasted for an hour, most of which I considered a study in human behavior. Or more specifically, a survey of the unconfident male. Sure, we all have our insecurities, but they’re no excuse for predatory behavior. Women can see right through these toxic tendencies.

Below is a breakdown of the ways men who lack confidence can sometimes inflict their own internal struggles on those who they date. If you recognize yourself below, perhaps it’s time to take a step back and work on yourself.

1. He requires alcohol to drum up the gumption to interact with women



Elisabeth Ovesen | NYT Bestselling Author
Writer for

3x New York Times Bestselling Author | 'The House of Ill Repute (Kensington Publishing, 2024)