Some dating coaches focus on helping you navigate the situation in front of you through practical, tactical advice. Others focus on helping you understand the man behind the situation—reshaping the way you think, while still solving the tactical problem when the time is right.

When people think about coaching, they often imagine asking a question and receiving an answer.

• “What should I text her?”
• “How should I respond?”
• “What should I have said?”

There is nothing inherently wrong with that. In fact, there are situations where a direct answer is exactly what someone needs.

But over the years, I’ve realised that coaching can happen on different levels.

One level focuses on solving the immediate problem.

Another focuses on understanding the person behind the problem.

Neither is universally better than the other. They simply serve different purposes.

A Conversation With a Client

A client of mine lives in Europe.

While visiting India, he was introduced to a woman through a mutual friend and they went on a blind date.

During the date, he openly told her that he didn’t think a relationship would work because of the long distance.

It was an honest conversation, and they left on good terms.

Later that evening, however, he found himself wanting to see her again. He messaged her, and she agreed to meet him for breakfast the next morning at her place.

While they were having breakfast, she suddenly looked at him and asked,

“Why are you here?”

He froze.

After a brief pause, he replied,

“I wanted to spend time with you.”

According to him, the atmosphere gradually changed after that moment.

A few days later, he called me.

His question was simple.

“What should I have said?”

The Transactional Approach

A transactional coaching conversation focuses on solving the immediate challenge.

The coach listens to the situation and offers a practical solution.

Depending on the coach, the advice might sound like this:

“You could have answered playfully.”

“You could have flirted instead of explaining yourself.”

“You could have said that you enjoyed her company and wanted to know her better.”

Sometimes a client has already done the deeper work. Sometimes he simply needs another perspective or a practical suggestion.

Transactional coaching is valuable because it provides clarity, direction and actionable solutions that can immediately improve future interactions.

The Transformational Approach

Instead of answering his question immediately, I became curious about something else.

I asked him,

“You had already told her that long distance wouldn’t work. So what made you message her again?”

He answered.

Then I asked,

“What do you mean by that?”

As he reflected, I continued asking questions.

Not to interrogate him.

But to understand him.

Gradually, we moved away from finding a better sentence and started understanding the thinking that led him there.

Was he hoping she would change his mind?

Does he just wanted to get laid?

Was there a part of him that wanted connection despite believing it wouldn’t work?

Each answer uncovered another layer.

Eventually we arrived at something honest.

He wanted to get laid before leaving for Europe.

Only then did we discuss what he could have said when she asked,

“Why are you here?”

The response we crafted wasn’t designed to sound clever. It was designed to align with his honest intentions while remaining socially calibrated.

We eventually arrived at two responses. I left it up to him to choose the one that felt most natural to him.

1. “Just to try my luck” – Only if said in a cheeky manner.
2. “I know this would not work practically speaking, but I still wanted to be in a close proximity of you” – This needs to be said with locking eyes, and even attempt a kiss after saying it. 

His first respond to me, upon hearing the crafted responses, was,

“Isn’t that too bold or straightforward?”, “Won’t she be offended?”

This lead to another round of questions, and reflection.

We came to the conclusion that he was feeling ashamed deep within even to confront the fact that, he just wanted to get laid.

This is where coaching moved beyond communication.

The problem was never finding a better sentence.

The problem was that he wasn’t comfortable owning his own intentions.

Once he became honest with himself, finding the right words became surprisingly easy.

Another Example

An Indian client of mine, based in Singapore, wanted to build a richer social life.

One of the first things we worked on wasn’t approaching women.

It was changing his lifestyle.

He began working from cafés twice a week instead of staying home. He found genuine reasons to spend more time in malls, accompanied his outgoing friends to cocktail bars around Pekin Street, went for evening runs around Marina Bay, and attended organised social events.

Naturally, he started encountering far more women than before.

A few months later, he came back to me with a different challenge.

“I’m meeting a lot more women now, but I’m struggling to make a meaningful impression.”

He also realised that many situations weren’t suitable for direct conversations.

Sometimes the woman was with colleagues.

Sometimes she was surrounded by friends.

Sometimes the moment simply didn’t allow for an approach.

He had already read my guide on speaking with your eyes, but he wanted to develop the skill in real life.

So we decided to spend five days together in Bangkok.

Rather than creating artificial exercises, we recreated environments that closely resembled the situations he regularly encountered in Singapore.

A Transactional Coaching Approach

A transactional coaching session would focus primarily on helping him navigate those situations more effectively.

For example, I might teach him how to:

• Hold eye contact for a few seconds.
• Wait for her to notice him before smiling.
• Position himself naturally.
• Use a situational opener if an opportunity presents itself.
• Build emotional engagement through storytelling.
• Ask thoughtful follow-up questions.

These are valuable skills. In fact, every man who wants to become socially confident should learn them.

There is absolutely nothing wrong with this approach.

For many men, practical guidance is exactly what they need.

A Transformational Coaching Approach

We certainly practised all of those skills.

But we didn’t stop there.

Before each interaction, I wanted to understand what was happening inside him.

Even before we walked into a venue, I guided him through creative visualisation exercises.

I asked him to imagine himself making comfortable eye contact, smiling naturally, remaining calm, and feeling self-assured.

I also asked him to visualise something most people avoid imagining.

A woman not responding.

Looking away.

Even reacting negatively.

Then I asked him to visualise himself remaining composed anyway.

Because confidence isn’t built by imagining perfect outcomes.

It’s built by becoming emotionally prepared for imperfect ones.

That was only one part of the process.

Once we were out in the real world, I wasn’t only observing the women around him.

I was observing him.

• His eyes.
• His breathing.
• His posture.
• His hesitation.
• The moments where his energy changed.

At one social event, I noticed him looking at a woman several times.

Each time, he looked away before she noticed him.

I asked him,

“I noticed you looked at her a few times. What’s going through your mind right now?”

He replied,

“I want to do something. She’s cute.”

I asked,

“What’s stopping you?”

He paused.

“I’m nervous.”

I continued,

“Nervous about what?”

After thinking for a moment, he replied,

“What if she thinks I’m a creep?”

He smiled,

“I don’t know.”

That was an important moment.

It wasn’t reality. It was an assumption.
So I took it one step further.

“If she did react negatively, what would that mean about you?”

After another pause, he answered,

“I’d probably feel worthless.”

Now we weren’t talking about eye contact anymore.

We were talking about self-worth.

That conversation didn’t replace the practical coaching.

It complemented it.

After understanding what was holding him back internally, we returned to the tactical work.

We practised positioning.

• Timing
• Eye contact
• Smiling
• Reading non-verbal responses
• Following up appropriately.

He then practiced the tactical non-verbal act under my guidance, so that it feels safe for him and her.

Isn’t That Too Much Thinking?

Some people might argue that asking these questions creates analysis paralysis.

I see it differently.

Transformational coaching isn’t about stopping every interaction to analyse emotions.

It’s about gradually uncovering the patterns that repeatedly hold someone back.

As those patterns become clearer, they require less attention.

Over time, the deeper conversations become less frequent.

The tactical skills remain.

But now they’re being expressed by someone who is calmer, more self-aware, and no longer driven by the same fears.

That’s where I believe lasting change happens.

Final Thoughts

Transactional coaching and transformational coaching are not competing philosophies.

In fact, I believe they complement each other.

There are moments when a client simply needs practical guidance to navigate a situation.

There are other moments when solving the situation isn’t enough because the same patterns continue to repeat themselves.

The art of coaching lies in knowing when to teach the skill, and when to explore the person learning it.

For me, lasting transformation happens when both work together.

About Pratik J

Pratik Jain, is an international Dating and Transformation Coach for South Asian Men. He primarily works with men to reinvent themselves so they become compelling and desirable, socially and to women. Pratik travels across major global cities to work with his clients.