GITRMM 46: Why What You Wear On the First Date Really Matters

GITRMM 46: Why What You Wear On the First Date Really Matters

We’ve all heard the saying that you only get one chance to make a first impression, and it certainly is the case for men when meeting a woman out for a first date. Men are very visual, and it may seem like he’s not noticing the details of how you look or what you wear, but he very much is. This week, Lisa and Benjamin talk about how to dress for a date, especially the first one, that shows your authentic personality but doesn’t come across as though you are insecure or trying too hard. They also talk about the difference between showing up in a casual and comfortable way, and not putting in enough effort. Are you overdressing or do you need to jazz it up a little? Listen in and find out.

What You’ll Hear In This Episode:

  • How first date fashion can get in the way of making a connection with a man. 
  • What you or your girlfriends may think is cool and sexy may be overwhelming for a man, especially at first. 
  • What does a man think when he sees a woman that is overdressed? 
  • When a woman is dressed like a movie character or Halloween costume, men don’t see the real “her”, but instead an image or facade. 
  • How to embrace dressing with comfort and ease, but still look classic and classy. 
  • Okay, but what if you have a strong sense of style and want to show it off? 
  • Does how you dress really impact a man deciding to go on a second date with you? 
  • It’s a sign of good self esteem to dress with taste and be understated. 
  • Lisa and Benjamin’s Emotionally Naked 12 Week Course is all about authenticity and a step by step process of learning how to put your true self out there in every way, from your profile pictures to how you show up. 
  • But wait, he’s putting in little to no effort in how HE shows up? That’s not fair! 
  • A man wants a woman to be comfortable in her body. That’s a huge turn on.
  • Benjamin shares the biggest turn ONs and OFFs when it comes to makeup, shoes, and showing some sexy skin. 

Continue On Your Journey

Lisa Shield | YouTube | Facebook | Instagram | Book a Call With Lisa

Email the podcast at:




  • “If a man can’t get through that layer, he’s not going to call back for the second date because there is not that connection.” – Benjamin
  • “It’s become more clear to me how important clothing and image is, and how that can completely draw someone in or turn someone completely off.” – Lisa 
  • “Some women so badly want to make an impression that they hide behind the fashion and they’re afraid to show their real selves.” – Lisa 
  • “We don’t necessarily want fireworks in the beginning, we want something to build from a  foundation of friendship, trust, and safety.” – Benjamin