Podcasts > Creating Confidence with Heather Monahan > #520 What He’s Really Thinking in the First 3 Dates: Flirting, Communication & Navigating the Early Days of Dating with Dating Strategist Ben Hart

#520 What He’s Really Thinking in the First 3 Dates: Flirting, Communication & Navigating the Early Days of Dating with Dating Strategist Ben Hart

By Heather Monahan

On Creating Confidence with Heather Monahan, dating strategist Ben Hart examines the different challenges men and women face in the dating landscape. Hart and Monahan discuss how women often create narratives about their dates based on limited information, struggle with vulnerability, and may invest emotionally before securing commitment.

The conversation explores practical dating strategies, including the role of feminine energy, effective communication techniques, and building confidence through small steps. Hart explains how men and women approach dating differently: while men focus on getting first dates and handling frequent rejection, women tend to face challenges in the subsequent stages of dating and may hold onto idealistic expectations about relationships.

#520 What He’s Really Thinking in the First 3 Dates: Flirting, Communication & Navigating the Early Days of Dating with Dating Strategist Ben Hart

This is a preview of the Shortform summary of the May 13, 2025 episode of the Creating Confidence with Heather Monahan

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#520 What He’s Really Thinking in the First 3 Dates: Flirting, Communication & Navigating the Early Days of Dating with Dating Strategist Ben Hart

1-Page Summary

Common Dating Challenges For Women

Ben Hart explores the emotional complexities women face in early dating stages. He notes that women often create narratives about a man's feelings based on limited information and may struggle with vulnerability. After the first few dates, Hart observes that women tend to invest emotionally before securing commitment and might hesitate to communicate their needs directly, leading to misunderstandings.

Strategies For Women to Improve Dating Lives

According to Hart, femininity is a powerful tool in dating. He recommends specific actions like maintaining eye contact, smiling, and light touching to spark interest. Hart advises against confrontational behavior, instead encouraging clear communication about intentions. He suggests that women should expect commitment after two and a half to three months of consistent dating, and be prepared to leave if it's not forthcoming.

Role of Mindset and Intention in Dating Success

In their discussion, Hart and Heather Monahan emphasize the importance of approaching dating strategically rather than passively waiting for relationships to "just happen." Hart advocates for building confidence through small, manageable steps like initiating conversations and maintaining eye contact, while keeping the focus on enjoying the dating process rather than overthinking it.

Gender Differences in Dating Experiences and Approaches

Hart explains that men and women face different challenges in dating: men primarily struggle with securing first dates, while women encounter difficulties afterward. He notes that men typically handle rejection more frequently, while women often fear vulnerability. Hart observes that men tend to approach dating strategically, while women may hold onto "fairy tale" expectations, leading to potential misunderstandings between genders.

1-Page Summary

Additional Materials

Counterarguments

  • While femininity can be a powerful tool in dating, it's important to recognize that not all women may feel comfortable or authentic using traditional expressions of femininity to attract a partner.
  • The recommendation to expect commitment after two and a half to three months of consistent dating may not apply to all relationships, as individuals and relationships vary greatly in how they develop and what timeline they follow.
  • The idea that women should be prepared to leave if commitment is not forthcoming could be seen as a rigid approach to relationships, which may not allow for the complexities and nuances of individual circumstances.
  • The suggestion that women often create narratives about a man's feelings based on limited information could be seen as a generalization that doesn't account for the diverse ways in which women understand and interpret the behavior of others.
  • The notion that women tend to invest emotionally before securing commitment might not reflect the experiences of all women, as some may be more cautious or take longer to develop emotional investment.
  • The assertion that men handle rejection more frequently than women could be challenged by the perspective that women also face rejection, but it may manifest in different stages or forms within the dating process.
  • The idea that men approach dating strategically while women hold onto "fairy tale" expectations could be seen as a stereotype that doesn't account for the varied approaches to dating that both men and women can have.
  • The emphasis on non-confrontational behavior and clear communication about intentions may not address the deeper issues of power dynamics and communication styles in relationships.
  • The advice to use specific actions like maintaining eye contact, smiling, and light touching to spark interest may not be universally effective or comfortable for all individuals, and could be seen as too prescriptive.
  • The concept of approaching dating strategically and with intention may not resonate with everyone, as some may prefer a more organic or less structured approach to finding a partner.

Actionables

  • You can create a personal "dating journal" to track your emotional investment and vulnerability levels. Start by jotting down your feelings and expectations after each date, noting when you start to feel vulnerable and how you handle it. This will help you become more aware of your emotional patterns and may guide you in pacing your emotional investment more effectively.
  • Develop a "needs and wants" communication plan for dating. Write down your core needs and wants in a relationship, and practice articulating them clearly in a low-pressure environment, like with a friend or in front of a mirror. This exercise will prepare you to communicate your needs directly and confidently when dating.
  • Engage in a "commitment clarity" exercise with potential partners. After a month of dating, initiate a casual conversation to gauge each other's expectations and intentions. This doesn't need to be a heavy "define the relationship" talk but should be a check-in to ensure both parties are on the same page, helping to set a timeline for commitment that aligns with your dating strategy.

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#520 What He’s Really Thinking in the First 3 Dates: Flirting, Communication & Navigating the Early Days of Dating with Dating Strategist Ben Hart

Common Dating Challenges For Women

Ben Hart sheds light on the emotional and communicative hurdles women often face in the early stages of dating and relationships.

Women Struggle With Composure and Attachment Early In Dating

Women may experience a torrent of emotions and concerns when entering the dating scene, which Ben Hart captures through common behavioral patterns and thought processes.

Women May Create Untrue Stories From a Man's Words or Actions

Hart talks about the confusion and frustration women face while trying to decipher a man's feelings. They often interpret a man's words and actions to form narratives that may not be true, particularly when he does not contact them for a week, leaving them in a state of uncertainty.

Women May Struggle to Open Up To Desired Partners

In the initial phases of dating, women may fear being vulnerable with the men they are interested in. This can lead to a struggle in opening up, which is a natural response to the uncertainty that comes with new romantic interests.

Women Navigate Relationships After the First Few Dates

After the excitement of the first few dates, women face the challenge of understanding the direction of the budding relationship.

Women May Invest In a Relationship Before Man's Commitment

Hart notes that women often start getting more invested in the men they are dating after the first few encounters. This investment can happen even if there hasn't been an explicit commitment from the man's side. Hart observes that women may choose to focus on one individual they find particularly appealing and may become attached prematurely, before a ...

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Common Dating Challenges For Women

Additional Materials

Counterarguments

  • While some women may face emotional and communicative hurdles, it's not universal; many women navigate early dating with confidence and clear communication.
  • Not all women create untrue narratives from men's words or actions; some may have a more pragmatic or straightforward approach to interpreting communication.
  • The struggle to open up is not exclusive to women; men can also have difficulties being vulnerable with potential partners.
  • Understanding the direction of a relationship is a challenge for both genders, not just women; men also seek clarity after initial dates.
  • Emotional investment before a commitment is not a behavior exclusive to women; men can also become prematurely attached in relationships.
  • The av ...

Actionables

  • Create a personal "dating communication charter" to clarify your emotional boundaries and expectations. Write down what you're comfortable sharing, your deal-breakers, and what you need to know from a partner to feel secure. This can serve as a guide for when to open up and how to steer conversations towards understanding each other's intentions.
  • Develop a "relationship roadmap" activity with a potential partner after a few dates. This involves sitting down together and sketching out what each of you envisions for the near future, including the pace of the relationship, commitment levels, and how you both view emotional investment. It's a collaborative way to ensure you're on the same page without putting undue pressure on either party.
  • Practice "scenario scripting" to improve direc ...

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#520 What He’s Really Thinking in the First 3 Dates: Flirting, Communication & Navigating the Early Days of Dating with Dating Strategist Ben Hart

Strategies For Women to Improve Dating Lives

Ben Hart speaks on the power of femininity and strategic communication in dating, offering women advice on attracting the right partner and navigating the complexities of modern relationships.

Ben Advises Women to Be More Feminine, Open, and Flirtatious to Attract the Right Partner

Ben Hart acknowledges that femininity is a powerful attribute and encourages women not to base their feminine side on how men make them feel. He suggests that actions like eye contact, smiling, and light touching can ignite a man's interest. Hart underscores the importance of these fundamental flirting techniques, which can prompt men to step up and express their interest.

Actions Like Eye Contact, Smiling, and Light Touching Can Ignite Interest

Hart further elaborates on actionable flirting tips, stressing the use of eye contact and looking back after passing a man as giving "the keys to the kingdom." He also talks about breaking the touch barrier, such as hooking a man's arm, to significantly enhance how he perceives a woman's interest.

Avoid Confrontational or "Ball-Busting" Behavior to Prevent Deterring Men

To avoid deterring potential partners, Hart suggests that women be softer, more open, caring, and present instead of being tough or confrontational on the surface. He warns that men tend to retract from women who are combative or present themselves as "ball busters."

Ben Advises Women to Communicate Clearly, Not Make Assumptions

Critical to maintaining a healthy dating life, Hart encourages women to communicate their intentions and desires for commitment clearly and calmly.

Women Should Directly Ask if a Man Pulls Away

According to Hart, if a man begins to pull away, women should not assume any reason behind his behavior but instead communicate directly to understand the situation. He is convinced that a woman cannot scare a man away by merely communicating, especially if he is truly interested.

Women Should Leave if a Man Lacks Commitment After a Reason ...

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Strategies For Women to Improve Dating Lives

Additional Materials

Counterarguments

  • Femininity is a diverse concept, and what is traditionally considered feminine may not resonate with all women or be attractive to all men.
  • Flirting techniques like eye contact and light touching may not be comfortable or appropriate for everyone, and relying on these actions can perpetuate the idea that physical attraction is the primary way to interest a partner.
  • The advice to avoid confrontational behavior could be interpreted as suggesting women should not assert themselves, which could undermine equality and the importance of having a voice in a relationship.
  • Clear communication is important, but the assumption that a man pulling away is a sign of disinterest may not always hold true; there could be other factors at play unrelated to the relationship.
  • Setting a strict timeframe for commitment can create unnecessary pressure and may not account for the individual pace at which a relationship naturally progresses.
  • The idea of leaving a relat ...

Actionables

  • Develop a personal charm routine by practicing positive body language in front of a mirror daily, focusing on aspects like your smile, eye contact, and posture to enhance your approachability.
    • By doing this, you create muscle memory for behaviors that signal openness and friendliness, making it easier to naturally exhibit these behaviors in social situations. For example, practice holding eye contact with your reflection for a few seconds longer than usual, or work on a smile that feels genuine and warm.
  • Create a "commitment clarity" journal where you note down your feelings, expectations, and experiences after dates to track patterns and decide on your commitment timeframe.
    • This helps you reflect on what you're looking for and whether your dates are aligning with your expectations. For instance, after a date, write down how you felt about the interaction, if your date showed signs of commitment, and how this fits into your ideal timeline for a relationship.
  • Initiate a monthly "relationship goals" ...

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#520 What He’s Really Thinking in the First 3 Dates: Flirting, Communication & Navigating the Early Days of Dating with Dating Strategist Ben Hart

Role of Mindset and Intention in Dating Success

Ben Hart and Heather Monahan discuss the importance of approaching dating with the same intention and structure that they apply to other successful areas of life.

Ben Advocates For a Strategic, Purposeful Approach To Dating Over a Passive One

Hart views the lack of a structured approach to dating as a challenge for many, contrasting it with the well-defined routines people have for work or exercise.

Haphazard Dating: Expecting It to "Happen"

People often expect romantic relationships to "just happen" without a deliberate strategy, which Hart finds unrealistic. He argues that dating has changed significantly, and that a structured approach might be more suitable for the modern dating landscape.

Intentional Mindset Leads To Better Dating Outcomes

Hart emphasizes the need for intentions and a purpose in dating, suggesting that such an approach will lead to better communication and understanding between partners. He thinks strategically about dating, contrasting this with the passive expectation that relationships will "just happen."

Ben Guides Women to Build Confidence Through Small Steps, Not Grand Goals

Hart focuses on building women's confidence through manageable actions and enjoying the process of dating without overthinking.

Actions Like Eye Contact or Initiating Conversation Boost a Woman's Self-Assurance

H ...

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Role of Mindset and Intention in Dating Success

Additional Materials

Counterarguments

  • Structured approaches to dating may not account for the spontaneous and unpredictable nature of human emotions and connections.
  • Overemphasis on strategy and intention might lead to viewing dating as a transactional process, which could detract from the authenticity of relationships.
  • The idea that a purposeful mindset always leads to better communication might not hold true for everyone, as some individuals may find that overthinking intentions can create pressure and hinder natural interaction.
  • Building confidence through small steps is valuable, but it might not address deeper issues of self-esteem that could affect dating success.
  • The focus on actions like eye contact and initiating conversations could inadvertently reinforce gender stereotypes about women needing to present themselves in a certain way to attract a partner.
  • The advice to focu ...

Actionables

- Create a personal dating plan by setting clear goals for what you want to achieve in your dating life, such as improving communication skills or finding a partner with specific qualities, and outline steps to reach these goals, like joining interest-based groups or practicing active listening during dates.

  • By having a roadmap, you can approach dating with intention and measure progress. For example, if you want to improve communication, you might decide to ask more open-ended questions on dates or reflect on past conversations to identify areas for improvement.
  • Develop a "confidence journal" where you record instances where you felt confident in social situations, noting what actions led to that feeling, such as making eye contact or initiating a conversation.
  • This journal serves as a personal feedback loop and a reminder of your capabilities. For instance, if you made eye contact with someone and it led to a pleasant exchange, jot it down. Over time, you'll have a collection of confidence-boosting actions to draw from.
  • Plan a series of "fun-focused" d ...

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#520 What He’s Really Thinking in the First 3 Dates: Flirting, Communication & Navigating the Early Days of Dating with Dating Strategist Ben Hart

Gender Differences in Dating Experiences and Approaches

Ben Hart and Heather Monahan explore how changing societal roles and expectations contribute to distinctly different dating challenges and perspectives for men and women.

Different Dating Struggles and Perspectives

Hart notes shifts in the dating landscape as a result of transitions within the workplace and societal expectations, affecting how both genders experience dating.

Men's Challenge: First Date; Women's: Afterward

According to Hart, men's dating struggles are largely focused on securing the first date, while women encounter their challenges after the first couple of dates. Hart notes men need to understand what women want to even get to the first date and must be aware of potential turn-offs or reasons for rejection.

Men Often Adapt To Rejection in Dating; Women May Fear Vulnerability

Hart explains that men are accustomed to dealing with rejection in the dating scene. Even successful or good-looking men are turned down more often than many women might expect. Hart suggests that viewing interaction and eye contact as natural rather than potentially facing failure can help individuals manage the fear of vulnerability. Heather Monahan echoes this, expressing agreement on handling fear of rejection.

Differing Mindsets and Expectations In Dating

The conversation reveals that men and women often enter the dating scene with significantly different mindsets, potentially leading to misunderstandings.

Men Are Strategic and Goal-Oriented; Women Envision "Fairy Tale" Dating

Hart points out that while many people harbor a Disney or fairy tale outlook on dating, thinking of it in strategic terms can be more practical. He asserts that women should consider the type of man they want and what that man is likely looking for, which reflects differing expectations and approaches between the genders.

Gender Differences May Cause Misunderstandings in Relationships

Men's hesitation to approach women m ...

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Gender Differences in Dating Experiences and Approaches

Additional Materials

Counterarguments

  • While men may often face rejection, it's important to recognize that women also experience rejection and may handle it in different ways.
  • The idea that women have a "fairy tale" perspective on dating could be an oversimplification and may not account for the diverse range of expectations and experiences among women.
  • Asserting that men are strategic and goal-oriented in dating could perpetuate stereotypes and overlook the fact that many men also desire emotional connection and not just strategic outcomes.
  • The notion that women's challenges in dating start after the first couple of dates might ignore the difficulties some women face in finding a first date or in navigating the dating scene more broadly.
  • The suggestion that successful women with masculine traits may affect male pursuit could be seen as reinforcing traditional gender roles and not considering that compatibility is more complex than a simple dynamic of masculine versus feminine traits.
  • The idea that men's hesitation to approach women is due to fear of social media backlash or being labeled as creepy might not take into account other factors such as personal insecurities, respect for women's space, or a ...

Actionables

  • You can create a balanced dating profile that showcases both your strategic and romantic sides to attract a partner who appreciates both aspects. For instance, mention your love for planning surprise getaways alongside your enjoyment of spontaneous adventures. This approach can help bridge the gap between strategic thinking and fairy tale expectations, making your profile appealing to a wider range of potential matches.
  • Develop a personal feedback system after dates to understand your dating patterns better. After each date, jot down what went well, what didn't, and any misunderstandings that may have occurred. Over time, you'll start to see patterns that can help you adjust your approach, such as realizing you may not be making enough eye contact or that you're better at communicating your interest through actions rather than words.
  • Practice expressing vulnerability in sa ...

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