Unlike in real life, where the purpose of a breakup is to end a relationship, break up emails have precisely the opposite objective. Break up emails are the last attempt to re-engage a prospect.

The reason is hardly difficult to understand. With a median ROI of 122% (Source), email marketing is extremely rewarding. No way a marketer would let go of their prospects easily.

What makes break up email unique in their challenge is that they are the last attempt to woo back your prospect (unless you plan to follow up with another break up email 🙂 ). That means they’re a last-ditch effort: if your prospect isn’t going to respond, you’ve lost them forever.

The good news is break up emails, when done right, can get your prospects respond quickly and positively.

Here are 5 simple break up emails that your prospects can’t resist reply.

1. The Humor Angle

Humor is effective, but it’s also risky. 

That’s because it’s highly culture-centric. Besides, humor can easily get distorted when you’re writing to someone whose first language isn’t the same as the one you’re writing the email in. Finally, there’s the risk it could fall flat and not leave the impact you thought it would.

That said, you’ll appreciate the following sample:

Sub: My first date and my emails

Hi Zac,

This isn’t something I’m proud of, but I’ll confess nevertheless.

The emails I keep sending you; they remind me of my first date!

My first date was with Niki and – you guessed it – I was stood up on that date! Yeah, like I waited for nearly an hour at Zoomies’, the great deli by my highschool, and she never turned up 🙁

And when you don’t respond to my emails, all those memories come back to haunt me. 

Any chance we can catch up on a 15-minute call later this week? Or is it goodbye for now?



PS: Despite that, I still think Niki is the nicest person I’ve known – we’ve been married for 12 years now!

The key factor: This is an example of self-deprecating humour. Because we’ve all heard such instances, it’s easy to identify with the situation.

The let-me-take-one-last-chance CTA (‘Any chance we can catch up…’) rounds off the email nicely.

And the last line ensures you don’t think Niki is a mean girl. And saying this shows you in good light as well!

2. The Exaggerated Story

Well, not so exaggerated as to make your prospects wince, just enough interesting to get you the email engagement you’re looking for.

Here goes:

Sub: Our elves are sobbing!

Hi Kelly,

Do you know we have small elves sitting inside our email system?

These elves are soft and sensitive creatures – and they get hurt a lot!

These elves really care for you – all they were looking for was a simple email reply from you!  

So like when we sent you three emails and you didn’t respond, they felt so deeply hurt. They sat in a corner and nearly wept themselves to death. No cake, no pastry would make them change their mind!

These elves have lost interest in everything else – they sit by our inbox all day long and keep staring and waiting for that ‘Ding!’ sound that’d ring out the moment your reply would land up in our inbox.

Kinda sad, ain’t it?

I’m not insisting you hit ‘Reply’ but if you think you’d like to light up their faces and their lives, that’d be the thing to do.

Will you? 

Or it’s just goodbye?



The key factor: Needs no explanation. It’s the story factor that keeps the prospect read on right till the end. 

And after that, the two words, ‘Will you?’ are short yet powerful enough to move the toughest negotiator. Email responses from your prospects will come in flying – be ready!

3. The Plainspeak Breakup Email

This style is not uncommon in email marketing yet it suits a few products and prospects and not others. 

Check it out:

Sub: Costs not a priority now?

Hi Alice,

I’ve written to you a few times but I haven’t heard back from you.

So I’m assuming improving staff productivity <or whatever is your key selling point> isn’t your current priority.

Anytime you need help with that, I’ll be happy to take it up again.

Take care.


The key factor: This is short and crisp, but there’s a subtle force here. Even while breaking up, you are hinting at what the prospect is missing by not responding (staff productivity, in this case).

This approach seems to work best when you’ve got the right prospect, like the ones Adapt brings you. The right prospect, by the way, is one whose profile best matches that of your buyer persona. 

Go ahead, try this clean-cut email.

4. The Reconnect Hook

Break up emails should not burn your bridges. 

When you’re saying goodbye, make sure you leave something with which to put your foot in again. Here’s a sample:

Sub: Your comprehensive guide

Hi Boris,

I haven’t heard from you so I’m assuming this isn’t the time you’d want to discuss how our <product feature>.

It just so happens that I found a comprehensive guide for companies considering import of casters <or whatever product>. I think you’ll find it hugely useful, so here it is:


Let me know when you’d again want to discuss this.



The key factor: This email looks like it’s an extension of the plainspeak break up email, but it’s not. The objective here is to share something valuable even when you’re not going to do business together, at least not right now.

So the focus here is to show how you genuinely want to help your prospect, sales or no sales. 

While this email cannot guarantee an immediate reply, you’ve already done a favor by sharing something of value. It’s a very small favor, but a favor nevertheless, and people are always keen to return the favor whenever possible.

As a result you’re going to be the first person your prospect will reach out to when they’re ready to discuss.

5. The Confident Email

It’s important to feel proud of whatever you sell. And it’s also important that this feeling comes through in the email nicely, without sounding vain.

Here’s an example of how you can use your faith in your product to get email responses:

Sub: Here’s why I’m so persistent

Hi Hafeez,

You’re probably wondering why I’m being so persistent. Am I so desperate to sell?

Yes, I’m keen to get this going but for a different reason. I’ve studied <name of prospect company> pretty closely. 

And I’m increasingly convinced your flattening sales curve can be upturned with the Sales Training Program (STP) we have in mind for you. 

Hafeez, I’m confident our 5-day STP will transform the way you close deals. And that’s why I simply don’t want<name of prospect company> to ignore this.

A short 10-minute call is all that will take to show you how this will work. 

I don’t see you saying no!



The key factor: This email rests on your, i.e. the sender’s confidence in the product. Directly relating the product you sell with the clear benefits your prospect will likely get is a great way to win back prospects. 

Phrases like I’m keen to… and I’m increasingly convinced … make this email sound like a friend making a product recommendation. Such a style is important, or the email would sound self-centered and fluffy.

Notice how the writer has used the prospect’s name in the middle of the email. That’s done to make this sound conversational and improve the chances of email engagement, but more importantly that’s done to shake off any impression of excessive pride the email might have given.