Asking My Date What His Biggest Insecurity Is Was The Best Icebreaker Ever

I decided to skip the small talk and cut right to the deep and meaningful stuff on a first date recently and boy, did it ever pay off. Here’s what happened and why you should give it a try.

  1. Who has time to talk about nothing? One of the most painful parts of a first date is the small talk. It usually ends up being something about the politics of the day or the weather or how the online dating experience has been. Ugh, boring. I didn’t want to have a shallow conversation this time—I wanted to get to the heart of things and quickly, so I dove in with a deep question and even though he was shocked at first, he eventually got into it.
  2. He admitted that no one had ever asked him something so personal before. I find that guys get serious about me really quickly because I pull stunts like asking my date was his biggest insecurity is 10 minutes into the date. I’m an open book and don’t mind sharing these deep, secretive things about myself. I find that guys find it pleasantly surprising when I take interest in their feelings because no one else really does.
  3. He admitted that he doesn’t think he’s good enough. His answer was not surprising at all. I’m certain that almost every waking person in this world has a fear of rejection or has felt overwhelmed by the idea that they’re inherently flawed. When he confessed that he didn’t think he was good enough, I had this deep sigh of relief because I was feeling the exact same thing (as most people do on a first date).
  4. It instantly made us feel closer to each other. Confessing our deepest insecurities from the beginning produced this vibe of camaraderie between us. It kinda felt like we were friends or at least really good acquaintances, like we had something in common. That made keeping the conversation going totally effortless.
  5. We both let our guards down. Something magical happens when you go deep and get vulnerable: you start to relax and just be yourself. He told me his biggest insecurity and then I told him mine and the second it was over, I felt so much calmer and like I could trust him. Once you know that the person you’re with accepts your biggest flaw, then you can kinda guarantee that they accept everything else about you. It’s a good feeling.
  6. He assumed I was joking at first by getting so real. The key to getting super deep right off the bat is to not go about it in an accusatory way or sound like you’re drilling your date with questions. I brought it up super casually and yeah, it was awkward for a couple of seconds, but then he saw that I wasn’t kidding. When that happened, he was actually into it.
  7. It led to some further deep conversations. The great thing about getting the heavy stuff out of the way is that it opened the floodgates to all of these other topics. What has been your most embarrassing moment? What are you most proud of in your life? Where do you see yourself in ten years? We didn’t feel like we had to impress each other, it was just where we naturally took the conversation.
  8. It felt like the fifth date rather than our first. It was super cool because by the end of the date, I felt like I’d known this guy for weeks. We got a lot of good conversation in and it was deep, meaningful conversation, not a sales pitch peppered with white lies which I feel most first dates tend to be.
  9. I feel like it’s better to be real and get rejected than to pretend you’re someone else and waste time. Going into this date, I knew I wanted to have a deep conversation and I was willing to take the risk that my date might think I’m a total weirdo for asking such prying questions. Still, I don’t see point in trying to present my perfect self for this stranger to get them to like me. I know that life is messy and I’m looking for someone who can appreciate that, someone who isn’t looking for a perfect dream girl. That’s just not me.
  10. We learned so much about each other. I got all the information I wanted and more and after just one date and now I’m able to make a decision on whether or not this could lead to something more serious. It was the most productive first date ever!
Jennifer is a playwright, dancer, and theatre nerd living in the big city of Toronto, Canada. She studied Creative Writing at Concordia University and works as a lifestyle writer who focuses on Health, B2B, Tech, Psychology, Science, Food Trends and Millennial Life. She's also a coreographer, playwright, and lyricist, with choreography credits for McMaster University’s “Spring Awakening,” “Roxanne” for the Guelph Contemporary Dance Festival, and “The Beaver Den” for The LOT, among others.

You can see more of her work on her Contently page and follow her on Instagram @jenniferenchin.