Have you ever gone on a date and felt like you were just going through the motions, talking about generic topics like the weather, hobbies, or work? Maybe you didn’t feel any chemistry or connection, and wondered why the conversation didn’t go deeper. If so, you’re not alone. Many people struggle with small talk on a first date, but few realize how crucial it is to push past it in order to create a meaningful connection.

As a matchmaker and dating coach, I’ve seen this pattern play out countless times. Clients come to me frustrated, disappointed after a lackluster date, wondering why they couldn’t connect with someone they found attractive or interesting. The truth is, attraction and interest are not enough to sustain a relationship. You also need vulnerability and authenticity, which are hard to cultivate if you stay in the shallow end of conversation.

So how do you push past small talk on a first date?

Here are some tips:

  1. Start by sharing something personal
    Instead of asking generic questions like “What do you do for fun?” or “Where did you grow up?”, try sharing something personal about yourself first. This can be a vulnerability, a struggle, a dream, or a passion. By opening up first, you signal to your date that you’re willing to be honest and real, and that you’re not afraid to show your true self. This can inspire them to open up to do the same.
  2. Ask open-ended questions
    When you do ask questions, make sure they are open-ended and not just yes-or-no questions. For example, instead of asking “Do you like to travel?”, ask “What’s the most memorable trip you’ve taken and why?” This invites your date to share a story, a feeling, or a perspective, which can lead to deeper conversation. You will get to know each other much faster this way.
  3. Don’t shy away from taboo topics
    While you don’t want to start a fight or offend your date, you also don’t want to shy away from topics that are important to you or that challenge the status quo. This can include religion, sex, mental health, or etc for example. By respectfully sharing your opinions and listening to theirs, you can learn a lot about each other’s values and beliefs, and see if you’re compatible in the long run.

Of course, pushing past small talk on a first date is not a guarantee to success. Chemistry and connection still matter, and not every date will lead to a second one. However, by being daring, vulnerable, and authentic, you increase your chances of finding someone who truly resonates with you, and who sees you for who you are.

So next time you go on a date, don’t be afraid to share some real sh*t! For all you know, it might be the start of something beautiful.



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