Podcast Summary: Ask the Dating Coach – “How Do I Start Conversations with Women without Making It Awkward?”

Podcast: How to Get a Girlfriend with Connell Barrett
Episode Air Date: November 19, 2025
Host: Connell Barrett

Episode Overview

In this “Ask the Dating Coach” installment, top dating coach Connell Barrett fields candid questions from listeners about some of modern dating’s trickiest hurdles: how to start conversations with women, making oneself more appealing and “pursuable,” overcoming insecurities about looks and height, and the real deal on what makes a man attractive. Connell breaks down persistent dating myths with humor and honesty, emphasizing “Radical Authenticity” as the key to confidence and connection—and swats down the manipulative tactics that plague so much online “advice.”
Main theme: Ditching scripts and gimmicks—bring your true self, build confidence, and connect authentically to attract the right partner.

Key Discussion Points & Insights

1. How to Get Women to “Chase” You (00:52)

• Listener Jason asks: “How do I make a woman chase me? What’s your advice on how to get a woman to show interest and pursue me? Seems like I’m always the one chasing.”
• Connell’s Perspective:
  • Debunking Pickup Tactics: Immediate rejection of the idea that lines and tactics can make women chase: “One of the biggest myths in dating…is this idea that you can make a woman ‘chase you’ just with certain lines or by tactical moves.”
  • The Truth: Women Chase Value, Not Tactics:
    “Women don’t chase lines and tactics…If she does not see you as somebody who adds something meaningful to her love life, she won’t chase you.” (03:52)
  • Online Example: Connell describes a client “Mickey” whose improved, authentic dating profile—showcasing real interests (like playing guitar)—led to women reaching out proactively.
  • Key Advice: "Make yourself so attractive, so authentically attractive to women that women who like your type are going to pursue you…The chasing will take care of itself." (06:30)
  • Personal Story: Shares how his now-girlfriend Jess texted him first after their initial date—not because of tactics, but “chemistry, fun, light banter…she saw in me, oh, this guy has real, real value to bring to my love life.” (08:01)

2. How to Start Conversations with Women Without Being Awkward (09:35)

• Listener Ken asks: “I’m shy. How do I start conversations with women in real life without being awkward?”
• Connell’s “What to Say” Method (A-B-C):
  • A: G-Rated Compliment – “Hey, you have really great style,” or, “I really like your tattoo.”
  • B: Contextual Question – E.g., at a coffee shop: “Hey, excuse me, are you going for iced coffee today or hot coffee?”
  • C: Observation – E.g., at a bar noticing matching drinks: “Hey, you guys have matching drinks. Interesting. What’s the story there?”
    “These three options work because they’re simple, they’re normal, they’re appropriate, they’re socially normal, they’re non creepy. You’ll always know what to say and you won’t have to plan it.” (11:45)
  • Mini-Story: He met an ex-girlfriend by approaching with a relevant question (about business books) in a bookstore—“all began with me just choosing that option.” (13:13)
  • Pro Tip: Avoid memorizing lines; instead, “just simply go with A, B, C.”

3. What Actually Attracts Women (Confidence & Radical Authenticity) (15:06)

• Listener Vikram asks: “What actually makes a woman attracted to a man?”
• Connell’s Analysis:
  • Almost All Women Want Confidence: “Pretty much every woman wants confidence. Pretty much every quality woman wants that.”
  • Radical Authenticity: The fastest path to confidence is embracing your romantic worth and being the real, unfiltered you.
  • Double Benefit:
    1. Authenticity = Confidence (women “can just smell that confidence on you like good cologne”)
    2. Authenticity = Trust (women need to know you’re genuine)
  • Personal Anecdote:
    Connell recalls approaching a woman by admitting his nerves and attraction:
    “Hi. I’m introverted and I’m shy, but you’re my type and I had to meet you. I’m Connell.”
    The woman was “blown away” by his honesty. (17:54)

4. The Myth of Looks—How Important is Physical Attractiveness? (24:54)

• Anonymous question: “How important are looks to women?”
• Connell’s Take:
  • “Looks don’t really matter all that much to women. Good looks are like jacuzzis in dating. They’re nice to have, but they’re way overrated.”
  • Men Project Visual Bias: Men value beauty and assume women do the same—it’s “just not so.”
  • The Data: Cites a health app (Clue) survey of 64,000 women (27:37):
    • Top 5 Male Partner Traits: 1) Kindness, 2) Intelligence, 3) Education, 4) Supportiveness, 5) Confidence.
      “Good looks did not even crack the top ten.”
  • Conclusion: “Bottom line is…women want swagger, confidence, a man with that steely self worth. And when you believe in your worth to women, you’re going to come off as sexy as Brad Pitt, even if you look like Brad Garrett.” (29:18)

5. Can You Overcome Height Insecurity? (32:00)

• Listener “John in Dallas” asks: He’s 5’4”, repeatedly rejected, considering an expensive, painful leg-lengthening surgery to get three extra inches of height.
• Connell’s Candid Response:
  • Joking Aside: “I know a guy down at the docks, Nicky the Nostril. He’ll do it for way less. Like 100 bucks.”
  • Serious Rebuttal:
    “Are you effing bonkers? Do not do this. Do not have your legs broken and lengthened. Height is not some magic pill.” (33:21)
  • Height ≠ Confidence: Even Connell at 6'2" had serious dating struggles until he worked on his inner confidence.
  • Height is Not the Issue:
    “The real issue…is how your height lowers your confidence…your very belief, your perception about your height that is hurting you so much more than your actual height.” (35:30)
  • More Perspective:
    • Many women just want a partner who isn’t shorter than themselves—being 5’4” is not a romantic death sentence.
    • “You don’t need towering height. You need towering confidence.”
    • “What’s hurting your love life isn’t your height. It’s how your height hurts your confidence and how that makes you insecure. That’s what turns women off.” (39:18)
  • Classic Connell Validation: “I tell every one of my clients, you are enough. You are enough. And in your case, John, I mean that literally.”

6. Bonus: First Kiss Technique (21:59)

• Listener Jeff in San Diego asks: “Women say I use too much tongue when going for the first kiss. Any advice?”
• Connell’s Quip: “If first kisses were movies, aim for Sleepless in Seattle, not Face Off.” (22:09)

Notable Quotes & Memorable Moments

• On Women Chasing Value:
  “Women don’t chase lines and tactics. You can use the best lines in the world, but if she does not see you as somebody who adds something meaningful to her love life, she won’t chase you.” (03:52)
• On Authenticity:
  “The fastest way to become confident is to become what I call radically authentic, which is simply about knowing your romantic worth to women and showing that worth as the real you.” (15:33)
• On the Importance of Looks:
  “Good looks are like jacuzzis in dating. They’re nice to have, but they’re way overrated.” (24:54)
• On Height and Confidence:
  “You don’t need towering height. You need towering confidence.” (40:09)
• On Flirting:
  “All began with me just choosing that [ABC] option. So it’s that simple. It’s as easy as A, B, C.” (13:13)
• On Being Enough:
  “You are enough. And in your case, John, I mean that literally. There is enough of you. You don’t need three more inches to become worthy of love. What you need is to see how worthy you already are and begin to believe that.” (41:03)

Key Segment Timestamps

• Myth of “Making Women Chase” Debunked: 00:52–08:20
• Connell’s ABC Approach to Starting Conversations: 09:35–14:00
• What Actually Attracts Women (Confidence & Authenticity): 15:06–21:58
• First Kiss Advice: 21:59–22:10
• Are Looks That Important? Survey Insights: 24:54–30:00
• Height Insecurity & Confidence: 32:00–41:30

Takeaways

• Drop the scripts and lines: Focus on real, value-driven connections rather than “chasing” gimmicks.
• ABC Method: Keep it simple, natural, and contextually appropriate; you’ll never run out of things to say.
• Raise your radical authenticity: Confidence and trustworthiness are what women crave—and, unlike looks or height, are fully within your power.
• Own your worth: You are enough, and you don’t need to change your looks or height to deserve love.

Connell Barrett’s final wisdom: "Build your confidence up from the core, from your very core, not from breaking your legs...What you need is to see how worthy you already are and begin to believe that." (41:03)

For more actionable insights, Connell invites listeners to book a call at datingtransformation.com.