Dating Success Story: How I Coached a 57-Year-Old Man Who Was Single for 35 Years to Become Engaged

Dating Success Story: How I Coached a 57-Year-Old Man Who Was Single for 35 Years to Become Engaged

Written by dating coach for men Gary Gunn - Founder of Social Attraction

Navigating the world of dating and relationships can be a daunting task, especially when you’ve been out of the game for a long time.

But that’s exactly the challenge my client faced—a 57-year-old man who had been single for 35 years.

The transformation he experienced was profound, and today I want to share some of the coaching techniques that made all the difference.

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Getting Him Out of His Comfort Zone

The first and perhaps the most crucial step was pushing my client beyond his comfort zone.

Through video coaching sessions, we did a series of role-plays that purposely led him to fail and get frustrated.

But that was part of the plan. Once he failed, I showed him a better, more effective way to approach the situation.

The goal was to make him understand that it’s okay to make mistakes, as long as he learns from them.

Over time, these new methods became automatic, replacing old, ineffective habits.

Sharpening His Flirting Skills

My client was already a fun guy, but he had a tendency to tense up around women, affecting his ability to flirt naturally.

So, we worked on making him more relaxed. By employing various exercises and techniques, he started to let his guard down.

The more relaxed he became, the easier it was for him to tap into his natural charm and flirt effectively.

Teaching Him How to Meet More Women and Spot Red Flags

The final part of our coaching focused on helping him meet more women, but with a twist.

I also trained him to spot red flags, which allowed him to be more selective about who he spent his time with.

We went through various scenarios and discussed what to look for in potential partners.

As he met more women, he also became more selective, ensuring a higher chance of finding a compatible match.

Teaching Him How to Give Value

Another essential element we focused on was teaching my client how to give value in his interactions.

This wasn’t just about impressing women with flashy tricks; it was about genuinely adding to the conversation.

We worked on storytelling techniques, encouraging him to include interesting facts and tidbits in his dialogue.

By choosing his words carefully and providing unique insights, he brought immense value to the conversations he had, making each interaction more meaningful.

Helping Him Make an Impact

Making an impact is not just about being heard; it’s about being remembered.

Alongside teaching him how to give value, we worked on how he could share the wisdom and life lessons he had gained over the years.

This allowed him to make a lasting impression, one that moved beyond mere attraction to genuine emotional connection.

His stories became more than just entertainment; they became impactful narratives that enriched the lives of those he interacted with.

Guiding Him to Be Himself

Last but certainly not least, we worked on helping my client be himself.

He’s an incredibly intelligent man with a wide-ranging vocabulary, and initially, he struggled to express this authentically.

Through coaching, we explored how he could channel his intelligence into engaging conversations without dumbing himself down.

We taught him how to speak about any topic in a manner that was not only intellectually stimulating but also deeply engaging for his listeners.

The engagement

After honing his skills, my client was not just ready to date; he was ready to find a meaningful relationship.

And that’s exactly what happened, he met a woman who was as intellectually stimulating as she was emotionally supportive.

But our coaching didn’t stop there.

We worked on relationship-building techniques, teaching him how to foster a strong emotional connection and open lines of communication with his new partner.

Topics like conflict resolution and emotional intelligence became crucial at this stage.

He was mindful of the red flags we had discussed but found none.

Instead, he found a partner who enriched his life and shared his values.

Within a year, he felt confident enough in his new skills and in his partnership that he took the big step: he proposed, and she said yes.

The next part of his life

The work we did together not only helped him find the right woman but ensured that he was entering this new chapter in his life as a more confident, more rounded individual.

Now, he’s not only excited for marriage but well-prepared for it.

In sum, the journey my client underwent was transformational on many levels.

He didn’t just learn how to date; he learned how to be in a relationship.

And most importantly, he learned how to be himself in that relationship, making it all the more rewarding for both him and his fiancée.


The journey may be challenging, but with the right tools and mindset, transformation is more than possible; it’s inevitable.

The journey to dating success is never a straight path, but with targeted coaching and a willingness to change, my client went from being single for 35 years to becoming engaged.

It’s a testament to the transformative power of stepping out of your comfort zone, honing your social skills, and being discerning in your choices.


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  1. Robert Cialdini, 1984 – “Influence: The Psychology of Persuasion” This seminal book by Robert Cialdini delves into the psychology behind how people are influenced by others. It provides scientific explanations for why methods that push people out of their comfort zones can be highly effective in changing behavior.
  2. Albert Mehrabian, 1971 – “Silent Messages” Mehrabian’s research emphasizes the importance of non-verbal cues in communication. His famous “7-38-55 Rule” outlines how 7% of any message is conveyed through words, 38% through vocal elements, and 55% through nonverbal elements like posture, facial expressions, and gestures.
  3. Carol Dweck, 2006 – “Mindset: The New Psychology of Success” Carol Dweck’s research focuses on the power of mindset and how a “growth mindset” can help individuals achieve their goals.

Written by Gary Gunn

Gary Gunn is a trained coach, accredited therapist and best selling author. He offers proven, evidence-based dating advice for single men.

He has hosted over 1,000 in-person dating confidence courses across the UK and Europe, as well as over 1,500 online courses.

As the head coach at Social Attraction, he leads the team and oversees the training and courses provided, helping countless men transform their dating lives.
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