Podcast Summary: Creating Confidence with Heather Monahan

Episode: #520
Title: What He’s Really Thinking in the First 3 Dates: Flirting, Communication & Navigating the Early Days of Dating with Dating Strategist Ben Hart
Release Date: May 13, 2025
Guest: Ben Hart, Dating Strategist

1. Introduction and Guest Overview

In episode #520 of Creating Confidence with Heather Monahan, host Nico welcomes Ben Hart, a globally recognized dating strategist, author, and content creator with over 700,000 followers. Ben is renowned for his pragmatic and heartfelt approach to dating, focusing on authenticity and personal accountability. He is the founder of Dating with Purpose, a coaching program designed to help individuals create meaningful connections.

2. Ben Hart’s Journey to Dating Strategy

Ben shares his transition from the entrepreneurship space to becoming a dating strategist:

Ben Hart (04:28): "I came from the entrepreneurship space. I had a startup in my 20s, which merged with a media company. Transitioning to dating strategy was a natural progression as I became fascinated with the intricacies of attraction and interaction."

He explains how his content initially focused on high-level personal development but pivoted to dating through platforms like TikTok, allowing him to experiment without preconceived identities.

3. Challenges Women Face in Dating

Ben identifies two primary challenges women encounter in the dating scene:

1. Post-Date Commitment Struggles:

   • Unlike men who often grapple with securing the first date, women frequently struggle with maintaining momentum after the initial meeting.

   Ben Hart (09:44): "For women, the struggle typically starts past date one or three. They're trying to navigate how to maintain interest without getting overly attached to an outcome."

2. Approachability:

   • Many women inadvertently make themselves less approachable, hindering potential connections.

   Ben Hart (11:30): "A lot of women can get in their own way in terms of being approachable or open to the kind of guy they want."

4. Strategies for Navigating Early Dating Stages

Ben introduces practical frameworks to help women navigate the early stages of dating:

• PEST Framework:

  • Proximity: Being physically near potential partners.
  • Eye Contact: Making meaningful eye contact to signal interest.
  • Smile: Using smiles to appear friendly and approachable.

  Ben Hart (11:17): "Proximity, Eye contact, smile. These are the fundamentals of being approachable."

• Flirting Techniques:

  • Double Baggy Bonnie: Engaging in repeated eye contact to show interest.
  • Breaking the Touch Barrier: Initiating light, respectful physical contact to build connection.

  Ben Hart (32:24): "Breaking the touch barrier, like grabbing his arm while walking, makes a huge difference in how he treats you moving forward."

5. Communicating Intentions and Setting Boundaries

Effective communication is crucial for establishing intent and setting boundaries:

• Expressing Desire for Commitment:

  • Clearly articulate your intentions to seek commitment to avoid prolonged "situationships."

  Ben Hart (26:47): "Communicate thoroughly about what you are looking for. If he doesn't want to commit, then it's not the right fit."

• Avoiding Overanalysis:

  • Encourage women to let go of fear-based assumptions and instead engage in open dialogue.

  Ben Hart (46:22): "Don't live in regret. Don't make up a false story. Communicate your feelings and intentions."

6. Balancing Feminine and Masculine Energy

Ben discusses the impact of professional success on feminine presentation in dating:

• Navigating Masculine Traits:

  • Successful women may adopt more traditionally masculine traits, which can affect their approachability.

  Ben Hart (28:36): "Some women use their competitive streak to compete with men, which can make them appear unapproachable."

• Flirting to Balance Energy:

  • Incorporate softer, more open behaviors to enhance femininity without compromising strength.

  Ben Hart (32:24): "Flirting methods like eye contact and light touch help balance masculine and feminine energies."

7. Dealing with Pullbacks in Dating

Ben offers insights into handling situations where a partner becomes distant:

• Possible Reasons for Pulling Back:

  • Personal issues, loss of interest, or seeing someone else.

  Ben Hart (40:19): "He could be losing interest or might be seeing another girl. Without communication, it's hard to know the exact reason."

• Encouraging Communication:

  • Recommend reaching out to understand the partner’s perspective rather than making assumptions.

  Ben Hart (43:12): "If you want to find out, go find out. Communicate your concerns to avoid living in uncertainty."

8. Building Confidence Through Small Steps

Ben emphasizes the importance of incremental progress to build confidence:

• Small Bits of Progress:

  • Encouraging simple actions like making eye contact or initiating casual conversations.

  Ben Hart (49:00): "Start with small bits of progress. Go for a walk, make brief eye contact, and gradually build your confidence."

• Momentum as a Confidence Builder:

  • Small successes accumulate, fostering greater confidence and more significant achievements.

  Ben Hart (49:30): "These small bits of progress create momentum, which in turn builds your confidence over time."

9. Final Advice: Enjoy the Process and Reduce Consumption

Ben concludes with straightforward advice to enhance dating experiences:

• Consume Less, Enjoy More:

  • Limit excessive consumption of advice and focus on enjoying the dating process.

  Ben Hart (53:48): "Consume less and have some fun. Don't overcomplicate things by bombarding yourself with information."

• Live Authentically:

  • Encourage embracing authenticity and letting go of rigid expectations.

  Ben Hart (54:49): "Reframe your mindset and just live your life. Don't let overcomplicating diminish your experience."

10. Closing Remarks and How to Connect with Ben Hart

Ben shares ways for listeners to engage with his work:

Ben Hart (55:14): "You can find me at Benny Inc. on Instagram and TikTok, and join my Dating with Purpose community at bennyhartinc.com."

Nico wraps up the episode by emphasizing the value of Ben’s insights in fostering confidence and meaningful relationships.

Notable Quotes:

• Ben Hart (02:34): "If you don't think about dating or dating fundamentally with more purpose or more intention, then I don't see how you just expect things to happen."
• Ben Hart (11:17): "Proximity, Eye contact, smile. These are the fundamentals of being approachable."
• Ben Hart (26:47): "Communicate thoroughly about what you are looking for. If he doesn't want to commit, then it's not the right fit."
• Ben Hart (53:48): "Consume less and have some fun. Don't overcomplicate things by bombarding yourself with information."

This episode offers valuable insights and actionable strategies for women navigating the complexities of early-stage dating. By focusing on intentional actions, effective communication, and confidence-building, Ben Hart provides a roadmap for creating meaningful and fulfilling relationships.