GITRMM ep 19: The Real Reasons Your Date is Getting Derailed (And How to Get Back On Track), Part 2

GITRMM ep 19: The Real Reasons Your Date is Getting Derailed (And How to Get Back On Track), Part 2

In Part 2, Lisa and Benjamin continue their conversation about why your dates are getting derailed, and what to do about it! They discuss how to make a man feel like the most interesting man in the world with rich conversation that shows true interest and curiosity for his life. Find out what he really thinks about the way you dress, and tips for showing up in a way that highlights your assets but doesn’t give away too much. Lisa and Benjamin also talk about how to keep the conversation flowing and playful, along with exact scripts to say if he’s talking too much or too little. Warning: these tips may make you stand out and touch his heart!

What You’ll Hear In This Episode:

  • What type of conversation sends a man right to his heart on a date and makes him feel like you are truly interested in his life? 
  • Are you going on a fact finding mission and making him feel interrogated? Learn how to show that you are truly curious and impressed with who he is, and how you would love to fit into his world. 
  • What you wear matters. There are pitfalls to being over-stylized! Lisa and Benjamin give pointers for showing your style in a way that is tasteful, elegant, comfortable, and classic.
  • How to tactfully bring up to a man that he is rambling and how to insert yourself into the conversation without shaming him.
  • How to have a relatable and two-way conversation, rather than a man feeling like he is caught up in a dramatic episode of a soap opera! 

Continue On Your Journey

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Audrey Hepburn 


  •  “You are aiming for his heart with your questions, not his head.” – Lisa 
  • “No man feels comfortable on a date sitting across from someone whose life seems like a constant soap opera.” – Benjamin 
  • “A man would love for a woman to be really interested, and more than just asking superficial questions.” – Benjamin 
  • “That’s why we need a woman in our lives, because they touch us emotionally in a way that we don’t get from anything else.” – Benjamin 
  • “If a woman is overly stylized,  many men are going to see it as a costume rather than an expression of individuality.” – Benjamin