Top Questions Canadian Men Ask Their Dating Coach (And the Answers You Need)

When guys first come to me for coaching, they usually have one big question on their mind:

“Why the hell is this so hard?” 🤷‍♂️

Fair question.

Dating should feel natural—but in reality, it’s become a confusing mess of signals, ghosting, apps, and self-doubt.

As a Canadian dating coach, I’ve heard every question under the sun… and I’ve got real, practical answers.

Here are the top ones:

❓ “What do I say when I approach a woman?”

Whatever’s real.

Observe something, make a playful comment, and introduce yourself.

It’s not about being clever—it’s about being present and normal.

Example: “You look like someone with a dangerous caffeine habit. Is that your third coffee?” ☕

❓ “What if I get rejected?”

You will get rejected.

But rejection isn’t failure—it’s feedback.

Most women are rejecting your energy, not your existence.

Fix the delivery, not the person.

❓ “Do women even want to be approached anymore?”

Yes.

They just want to be approached well.

That means confidently, respectfully, and without acting like you're auditioning for The Bachelor.

❓ “Should I be dating online or in person?”

Both.

Online is efficient, but real-life approaches build confidence faster and give you way better feedback.

Also, fewer bots. 🤖

❓ “How long does it take to get good at this?”

It depends on how often you take action and how honest you’re willing to be.

With consistent coaching and practice?

Most guys start seeing big changes in just a few weeks.


The truth is, most men have the potential to be great with women.

They’re just lacking the guidance, structure, and live feedback to unlock it.

Go here to learn how coaching can help you. 👇

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