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Welcome to Day 10 of 30 Days of Dating Advice for Intellectual Badasses! If you’re just joining us or you want a recap of everything we’ve covered so far, I’ve created a summary page with a menu of everything we’ve discussed so far.

We’ve moved on to something not often talked about by dating experts: social skills. Today, I want to talk about a mistake many people inadvertently make when on a date or talking to someone they’re interested in. What is that mistake?

Trying to impress them.


Why Trying to Impress Your Date Backfires

It’s understandable that when you’re talking to someone you’re attracted to, you want to impress that person. You want them to like you, to find you interesting, to find you, well, impressive. Nothing wrong with that. The problem isn’t wanting to impress, it’s the things we do to impress.

I cannot tell you how many times I’ve had women tell me this:

“I went on this date with the cute guy, and I swear he talked the entire time. I barely said two words!

I’ve also had men tell me:

“I don’t know. She’s great – smart, attractive, accomplished… but it’s like she was trying too hard.”

In both examples, they were trying to impress their dates, and it backfired. Most of the time, your date won’t recognize that you’re trying to impress them. If they did, they’d probably give you another chance. Instead, they only see behavior they don’t like. They never make a connection with you.

Here are some examples of trying to impress on a date:

  • Being a chatterbox. Trying to impress often means talking too much. As I discuss in Changing Your Game, this is a common mistake men make, although talkative women will do this too. They mean well, but their date assumes they’re more interested in themselves than in her.
  • Bragging or listing accomplishments. I once had a guy tell me his bonuses were bigger than my annual income. Yes, he’d had a couple of drinks, and I was just beginning grad school and had the low income to go with it. In many cases, it never hurts to make others aware of your awesomeness. But when it’s clear you’re trying to do so, people can sense it and may assume you need too much ego-stroking.
  • Talking at your date. Have you ever talked with someone and felt like they were talking AT you, rather than WITH you? It’s almost as if they’re in a conversation with themselves, with you as the audience. Unlike the chatterbox, they will let you talk, but they’re so focused on getting their point across that they don’t seem to hear anything you say.

All of these behaviors cut you off from the person you’re talking to. So what do you do to avoid this? When talking to the other sex, whether on a date or in a conversation you hope leads to a date, try to CONNECT.


Connecting With People

People may respond to information; but they respond more to emotion. Why do you think great movies have powerful music soundtracks, and commercials for life insurance show us cute grandpas hugging cute kids? They’re trying to appeal to our emotions. And while dating shouldn’t be so overtly manipulative (yes, Pickup Artists, I’m talking to YOU), these movies and commercials can teach us something.

That “something” is that people don’t care as much about what you say – they care how you make them FEEL. They don’t want your stats; they want to feel a connection with you. And when you’re trying too hard to impress, you take away opportunities to do that.

So what do you do?

  • Start listening. When having a conversation, you impress people more NOT by what you say, but with your ability to take interest in what THEY say. Listen. Acknowledge their words. Ask follow-up questions.
  • Match your energy with theirs. When you’re trying too hard to impress, you give off a nervous energy that makes others uncomfortable. Dial down your voice level and chatter to mirror theirs.
  • Find common ground. To connect with someone, find out what you have in common. Are you both single parents? Are you both scientists? Are you both first-borns? Do you both watch Game of Thrones or have you both watched Princess Bride 50 times?
  • What makes them tick? Another way to establish a connection is to get them talking about what they’re passionate about. You’ll know because their face will light up and they’ll seem more engaged. If you haven’t hit this yet in the conversation, ask them their favorite activity or hobby.

Connecting with others is an art form that takes practice. But if you can accomplish this on a date, they are far more likely to be impressed with you.