The absolute truth about most men's deepest insecurities

Trey Hamilton
4 min readJun 2, 2024

I conducted my own poll with my 2700 Instagram followers a few days ago because I wanted to figure out how the men feel about dating and what some of their deepest insecurities are. I wanted to figure out how they felt! Here are some of the best responses!

  • “Wondering how I compared to the competition and her previous boyfriends.”
  • “Will she be able to understand the emotions or the side of me that people don’t usually see?”
  • “Am I interesting enough to be on her dating shortlist?”
  • “I struggle with financial expectations. I don’t really care about making six figures.”
  • “Can I provide enough, money-wise?”
  • “not being man enough. I’ve never really been an “alpha.”
  • ‘friend-zoned”
  • “Am I too boring?”
  • “Am I enough? And can I please her sexually?”
  • “Is she really interested in me?”
  • “When we get past all the initial flirting and joking around on the first date, she won’t like the real me.”
  • “If I show real interest, they won’t be interested anymore”
  • “I get texting anxiety.”
  • “spreading out response times to not come across as too needy…



Trey Hamilton

Author - The First Date Fix - Dating Coach - Content Creator -Dog Dad | follow me for some ramblings of a millennial who has dated. A LOT! TheFirstDateFix.Com