On my YouTube channel, I got a comment under one of my videos from a guy who said:

“I recently went on three dates with an attractive Eastern European woman — two great dates and one average date. On the morning of our fourth date, she canceled, saying she was sick. I replied, ‘Let me know when you’re free to meet again.’ Three days have passed, and I haven’t heard from her. So, I guess I got my answer from her actions.”

Guys, guys, guys — please stop asking women to “let you know when they’re free to meet again.”

I know some of you are thinking, “But Harry, if she had a high interest level in me, she would reach out and let me know when she’s available!”

And I get why you’d think that. Logically, if someone likes you, they should want to make time for you, right? If she’s interested, she should be the one to follow up and reschedule.

That’s how it should work. But that’s not how it actually works.

I’ve been through this enough times to know: when you put the responsibility in a woman’s hands to “let you know” when she’s available, more often than not, you’re never going to hear from her again.

And that’s because, in her mind, the way you phrased that message communicated something completely different than what you thought it did.

Why “Let Me Know When You’re Free” Kills Attraction

When you say “let me know when you’re free,” what you think you’re saying is:

“Hey, I respect your schedule, and I’m open to making something work when you’re feeling better.”

But what she hears is:

“I have nothing better going on in my life, so I’ll sit around waiting for you to decide when I get to see you again.”

It feels passive. It feels like you’re waiting for permission to be in her presence. And that’s just not attractive to women.

See, women are drawn to men who lead. They want a guy who takes charge and makes plans.

When you put the ball in her court like this, you’re making her the one who has to lead the interaction, and that’s a dynamic most women do not find appealing.

Even women who genuinely like you might start feeling off about you simply because of sending them this text.

A Better Approach

So what should you do instead?

Let’s say she cancels a date, saying she’s sick. First of all, pay attention to how she cancels.

If she cancels but immediately offers a counteroffer (like, “I’m sick today, but I’d love to see you next weekend if you’re free”), that’s a sign she’s still interested.
But if she cancels without offering an alternative, that’s a red flag. It means she may not be as invested as you think.
In either case, here’s what I’d say instead:

“Oh, you’re sick? Sorry to hear that. Hope you get better! I’ll be in touch soon.”

Then, leave her alone for at least a week before reaching out again.

Why This Works

• It keeps the ball in your court. Instead of waiting for her to make the next move, you are the one deciding when to follow up.
• It avoids making you look desperate. You’re not chasing, you’re not pleading, and you’re not putting your life on hold for her schedule.
• It gives her space to wonder about you. If she’s interested, she’ll notice your absence and think, “I wonder if he’s still into me?” That curiosity builds attraction.
• It signals that you have a life outside of her. Women are drawn to men who have purpose and ambition, not guys who are just waiting around for them.

Women Want You to Lead

Now, some guys will say, “But Harry, if she was really into me, she’d reach out first!”

Maybe. But in most cases, women don’t want to be the ones asking you out.

Even if she’s interested, she’ll hesitate to take on what she sees as the masculine role of pursuing you.

Even women who text you first, check in on you, and show interest still want you to be the one making the plans.

She wants you to make her feel like she’s being swept up in a romance, not like she’s the one doing the sweeping.

The Reality of Her Thought Process

Let’s break down what’s actually going on in her head.

If you say, “Let me know when you’re free,” she’s thinking:

“So… I have to be the one to plan this now? I have to reach out? What if I reach out and he says no? What if I seem desperate? Should I wait a few days? I don’t know… maybe I’ll just move on.”

Meanwhile, if you simply say, “Hope you get better! I’ll be in touch soon,” she feels relieved because she believes you’ll handle the next step.

What to Do Next

So, let’s go back to the guy who left that comment.

It’s been three days, and she hasn’t reached out. That’s not a good sign. And to be fair to this guy, based on how he said the 3rd date felt, chances are she was using the “I’m sick” excuse to get out of the date and stop seeing him altogether.

But there’s always a chance that it’s a misread and she’s still interested but legitimately was sick.

Either way, what we don’t want is for this guy to be left in limbo not being completely sure this woman is no longer interested.

So, instead of assuming she’s gone forever, I always recommend reaching out one more time as a way to double-check.

Send her a casual text like:

“Hey [her name], hope you’re feeling better. I was thinking about grabbing [activity/restaurant] this Tuesday or Thursday, lmk which works best for you.”

Then, see how she responds:

• If she’s interested, she’ll engage with you and set something up.
• If she’s lukewarm or noncommittal (“Oh, I’m not sure, maybe”), take that as your sign to move on.
• If she ghosts you, you’ve definitely got your answer.
• But never leave it open-ended with “Let me know when you’re free.” That phrase is a slow killer of attraction AND leaves you forever waiting for her to respond.

Final Thoughts

Look, I get it — this is a small tweak, but small things matter in dating. The words you use and the actions you take can make or break attraction.

Women are naturally drawn to men who lead, take charge, and make decisions. So don’t put the responsibility of planning the date in her hands. She doesn’t want that job.

Instead, own the process. Stay in control. And if she’s interested, she’ll follow your lead.

Let’s stop making this mistake in 2025, shall we?

– Harry Wilmington

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