Conversation Skills
For Men

How to message a woman you’ve messed it up with

November 13, 2020
▪ 5 mins read

What to do after you messed it up?

If you’ve been reading my latest text messaging advice*, you may now be looking back at some of your recent messages and thinking, `what damn! I wish I’d sent something different!’ So in this blog, I’m going to tackle how to message a woman you’ve messed it up with.  

*If you missed it make sure you play catch up here.  

But before we begin I want to ask you two quick questions to make sure this advice is 100% relevant to you.

1. Have you messed it up with her?

If she just hasn’t responded for a day, or she `usually’ messages more but now she hasn’t, or she’s late getting back to your last message - don’t panic!

Remember with messages if it hasn’t been 48 hours the rule of thumb is usually to chill out and see if it resolves itself.  

She may be taking some time to think how to respond, playing it cool by not responding too quickly, or just be busy with other things - sending multiple messages can pile on the pressure.  

One of the tricky parts of the early stages of dating is to not go down a rabbit hole of worrying about what she may or may not be thinking of you, so before jumping into action ask yourself, `was what I wrote that bad?’  

Messages I would class as `that bad’ include becoming angry when you shouldn’t have, breaking up with her then regretting it, going too sexual too soon etc.  

If she just stopped replying without any provocation, the chances are she got bored with the messages or felt they weren’t going anywhere. This may mean that your conversation needs a jump start - but the right way to do this isn’t via an apology.

2. Is it worth trying to win her back?

Before you say YES I want you to ask yourself this, `was she investing in me?’  

If you are thinking of messaging a woman you only had a handful of dates with, it may be wiser to let that one go, and focus instead on meeting new women.  

I know she may have really been your type, or maybe you feel like you made a rookie error that cost you her interest, but often when you find yourself pining after one woman who you’ve only had a very limited interaction with, this is a signal for you to meet new women!  

When you’re in a space of scarcity (read: `I hardly ever meet women I’m attracted to who are into me!’) it can make you hold on too tight to any opportunities that do arise. Instead of putting one woman on a pedestal though, it’s often better to discover how you can consistently meet the women you like.

Okay so let’s imagine your particular situation passes both these questions:

  • You’re sure you’ve messed it up with her
  • You’re sure she’s worth the extra effort to try to win back

What are your next steps?  

Let’s take the example of a woman you broke up with, and now you regret this.  

The first thing to note is during C19 women have had A LOT of men trying to come back into their lives; I have one female friend who had no fewer than 11 guys she dated trying to reconnect!!  

Women are pretty wise to the fact that men may stop dating them because they’re enjoying the single life; then when single life becomes less fun (thanks C19!) they’ll try to recover old interactions.  

It’s important then, that your interest is genuine, and if it is if you present it this way.  

No joke, one of the 11 guys mentioned above sent the message:  

 I mean, is it surprising this was met with an eye-roll of, `wow Deliveroo, so romantic? Is that really what was most memorable about your time with me?’  

You cannot appear that you’re using any old lame excuse to get back in touch: she’ll just think you’re bored and looking for someone to pass the time.

Be honest and direct

Instead, if she’s worth trying to win back I would be very honest and direct in what you write. Maybe something like this:  

Hey Em, I’m not sure if this message is expected, or not. But I’ve wanted to reach out for a while. I’ll be honest with you: I’ve been thinking about you a lot. You have every right to ignore this message, and if you do I will be conscious not to message again, but if you’re open to it - maybe I could give you a quick call this weekend? - Sam x

Let me break this down for you:

Hey Em, I’m not sure if this message is expected, or not. But I’ve wanted to reach out for a while.  

This tries to imply that you’re not just messaging her in the spur of the moment because you’re bored, lonely etc; but it’s been something you’ve contemplated for a while. This communicates that you’re sincere.  

I’ll be honest with you: I’ve been thinking about you a lot.  

This part of the message communicates honesty and vulnerability. You’re laying it all on the line. This is very attractive as you’re being direct about what your intentions are.  

You have every right to ignore this message,  

If she’s thinking of not responding, this shows you empathise with her and can help to remove some of her doubts.  

and if you do I will be conscious not to message again  

This also lets her know that you won’t be getting in touch again: it’s a one time offer!  

but if you’re open to it - maybe I could give you a quick call this weekend?  The last part of the message creates an action step for how to move things forward. Note: she may not take you up on the phone call, but may well offer you a lower investment way forwards by responding to your text.  


And that’s the nuts of what messages to send to win a woman back.

Needless to say, please only use these messages when you have a sincere interest. I want you to back up great messages with great actions!  

Hopefully, from reading these emails and blogs you’ve started to see how important getting this area of communication nailed is -- without it, you can have all the right intentions but these may never come across to her.  

As you know I’m hosting a special one-off webinar on how to become a Master Messenger.

The details....

Time: 4 PM London time  

Date: 12 Dec 2020  

How Do I Join?:  

You’ll also be pleased to hear that I’ve got extra spaces allocated for this webinar session, so as long as you have a decent internet connection you will be able to participate but you do need to register your place using this link.  

I’ll be excited to see you there!  


Hayley x  

P.S. Check out the guest post by one of my Team HQ coaches, Jack, on how to get your ex-girlfriend back.  

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