Cruelest Ways To Break Someone’s Heart Gently (21 Ways)

A quick search on the internet will bring multiple ways to initiate a breakup, with many of the results prioritizing tact. I can’t say there’s ever a smooth, compassionate way to break someone’s heart, but I do know there are levels to how harshly people deliver the blow. 

Even then, being gentle about a breakup doesn’t always exclude cruelty. In some cases, it can be even more painful than some overtly mean alternatives. On that note, here are some of the cruelest ways to break up with someone gently. News flash: you’ve likely done at least one of them before.

23 Cruelest Ways To Break Someone’s Heart Gently

1. Encouraging them to get vulnerable then withdraw

This is certainly one of the cruelest ways to break someone's heart. Even if you acted normal right after, there’s this thing about letting your guard down that makes one anxious. It’s natural for someone to read into every little thing after opening up about their insecurities or anything else that gives them the idea you might look at them differently.

When will you choose that period to initiate the slow fade? In case you are not familiar with the term, the slow (or gradual) fade is when a prospect slowly lets communication decline, and the vibe between you deteriorates as a result. 

I mean, it hurts to get that reaction from a stranger you only just matched with, much less someone you’ve grown comfortable enough with to be unguarded around. 

2. Reassuring them they are the only one then get caught cheating

Cheating is admittedly one of the worst ways to end a relationship, but it outrightly becomes cruel when you get caught doing it after specifically promising not to. When you go out of your way to make someone believe that you’re the exception, and then you are pants down, doing exactly what you swore unprovoked never to do.

It’s worse when it’s the first time. If the betraying partner has been nothing short of upstanding till that moment, you might even blame yourself, thinking you pushed them to someone else’s arms by something you did. 

So, alongside nursing a broken heart, you still go about doubting yourself and your capacity for relationships, weighing what-ifs, which is just brutal.

3. Telling them you’ve found someone else

Compared to some other ways to break someone’s heart, this is supposed to be this noble, truth-telling move they’ll probably give you points for in the future. Honesty may be the best policy, but, as you know, it doesn’t make it any easier to swallow in the now. 

Telling someone still totally into you or has been doing their best to make things work between you that you’ve met another will devastate them no matter how you put it. Even if things had been rocky up to that moment, the very fact that you found it pertinent to come out and say it means it must be serious. 

Wondering what the other person has that you don’t, possibly even long after the relationship has ended, is simply heartbreaking.

4. Falling in love with their best friend or sibling

Now it’s bad enough getting dumped for just about anyone, but when you find out the other person is your own blood? Yes, that’s brutal. If you think it’s painful having to deal with losing a promising romantic prospect, imagine how worse it must feel when the one person you cry to is the ‘someone else’.

This is cruel in so many ways, but perhaps what stands out the most is how you inadvertently gaslight yourself to defend the reality. Like the signs might be right there in front of you, and you’d still justify them thinking, my partner could never do that to me, and if they did, my best friend would never. 

Then you find out just how colossally wrong you are when the breakup conversation finally happens, and they tell you they are in love.

5. Flirting openly with someone else while they watch

Breaking someone’s heart isn’t limited to relationships alone, and one cruel way to do it across the board is by flirting. The more common scenario, of course, is between non-couples, people who are romantically entangled but are yet to slap a label on it or make it public.

It is also likely to happen among recently separated exes and unrequited lovers who have to watch the person they are into, flirt with another in their presence. I’m sure I don’t have to explain how jealousy works, but more often than not, it’s the blatant disregard for the other’s feelings that makes it even worse.

6. Switching up on them suddenly with no explanation

Relationship or otherwise, people act out sometimes, that’s just the way it is. Usually though, the ones closest to you have an inkling why or at least they should. But I don’t know which is worse, between not being counted as close enough to warrant the details or basically being the next of kin and still being kept out of the loop.

Whether your relationship is only a few dates strong or it’s been years, having to fill in the gap yourself that only the person who created it can, would make anyone spiral. But obviously, the more invested you are in it, the more terrible the feeling.

7. Making them feel guilty for what went wrong in your relationship

Sometimes, people end things for pointed reasons like cheating, but the reasons for a breakup are not usually as clear-cut in many more cases. Either someone gives up too soon, or the other isn’t committed enough to walk the talk. More often than not, each party involved has their share of the blame.

Now, those whose first intuition is to get out of taking responsibility may find this to be their go-to breakup method. It’s never something they could have done better themselves, but their ex’s entire fault when things don’t work out. That may not seem so grave compared to other specific ways on this list, but it’s one of those if you know you know situations.

8. Ignoring their heartfelt gesture

Having someone bare their heart to you, just to have you stomp on it by not even finding it deserving of a response, is another across-board way to crush them. It’s basic courtesy to return such a gesture with at least an acknowledgment, if not full-blown gratitude, and as such, being ignored altogether can make one feel grossly unworthy.

It could be a love letter or a proposal, heck, even a text message to check-in. Regardless of the specifics, as long as the sender is risking putting themselves out there and the recipient acts like they couldn’t care less, it counts as brutal.

9. Ghosting them

Though common, ghosting is considered the absolute worst way to end things for the simple reason it robs the ghosted party of what everyone needs to get through a breakup – closure. Unlike the slow fade option, where you may see the signals if you know where to look, this one doesn’t leave much clue or reason. 

One minute you are a unit, talking every day and all, the next, they are just gone. The hardest part is determining when to kickstart the healing process, amidst wondering what could have possibly gone wrong and whether they’ll come back. 

Don’t even get me started on how ghosting can be a trigger for those suffering from self-esteem or abandonment issues and how it can mark the beginning of it for those who don’t.

10. Reminding someone you dumped about ‘the good old days’ when they’re on the verge of moving on

Speaking of, you can break someone if you not only deny them closure from you and what you had but also intentionally deter their healing process so they can’t move on. Take, for instance, someone you dumped knowing they still love you. They go through all the steps, from trying to get back together to mourning the relationship and finally trying to get back out there.

Now, if you do nothing the whole time, just to resurface when it seems like they might actually have a chance hoping to send them back to square one, you are cruel.

11. Having your new fling pick up their call before the breakup is official

You may have heard of couples who end things because one partner was having an affair and parading it before the separation is even official. Like most cheaters become remorseful when caught, but at the same time, many don’t.

Even though it’s an unhappy relationship that’s more likely to meet that kind of end, it still sucks to see someone who used to respect you hurt you so nonchalantly. And in cases when it’s purely an accident that the new bae picks up, it still hurts a bit extra to think they don’t rate you enough between them to be more careful.

12. Living and flaunting your happily-ever-after with someone else after ruining them

Not all exes hate each other for breaking up, some choose to leave the door of friendship open, perhaps for the children or just for the sentiment. However, even the most functional of such dynamics can get rocked by anger, sadness, envy, and other related negative emotions when the new relationship appears to be everything the last one wasn’t.

The happily-ever-after can be even harder to bear for someone who only got the worst of their ex and now has to watch them share their dream with a new partner.

13. Giving a backhanded compliment about their skill/talent

Cruel ways to break someone’s heart nicely even if you’re only just meeting? Compliment them, but make it backhanded. Like telling someone who loves to cook that their food is okay, but not everyone is built for the line of work. Or telling a singer they sing beautifully for a girl/boy.

Basically, any remark suggesting or reinforcing the idea that you didn’t think they could do something cloaked as a compliment. Also, praises followed by unsolicited advice/comment on something unusual about someone at the expense of their norm. E.g., you look good today, you should wear your hair like this more often. 

14. Emotionally manipulating them to stay in a relationship you know won’t lead anywhere

Breadcrumbing, or whatever the term is for leading someone on even though you have little or no interest in taking things further with them, can be cruel too. You don’t want someone else to have them yet fail to invest what they need to feel secure with you, essentially leaving them in limbo the whole time.

People who find themselves in such a manipulative dynamic always wait for the other shoe to drop, never assured of what side of their partner they’re going to get each time. This is emotional hell, and it gets way more heinous, tending on abuse when the breadcrumber puts their mind to it.

15. Making time for everything but them

Do you know how much it sucks to have everyone else describe your significant other as thoughtful and present when you literally cannot relate to that? They are not exactly mean to you, that would require actually paying you some attention outside of the need-tos. No, they just never have time for much of anything that involves you.

Likewise, it would hurt even more to see such an ex who was ‘always busy’ while you were together doting on their new partner. Even if a lot of it had to do with circumstances in your time, you still can’t help but draw the heartrending conclusion that it must be personal. That they must not have loved you if making you a priority despite the odds was so hard.

16. Announcing a serious relationship with another while you’re “together”

Picture this: you’ve been fooling around with this person for a while but haven't actually talked about what this is. Then you begin to catch feelings, but when you gather the courage to initiate the DTR conversation, the unexpected happens. 

You open social media to find a whole wedding invite/engagement announcement without so much as a heads-up from them about being in a relationship. Though nothing has exactly been promised yet in this scenario, it can still take the jilted person some time to heal, forget, or trust again, if ever.

17. Feeding them an obvious lie about why things are no longer the same

Even if you’re breaking up with someone, insulting their intelligence to soften the blow or whatever is just annoying. Especially when the go-to lie is something as see-through as the famous “it’s not you, it’s me.”

I mentioned earlier about honesty not making bad news any easier to receive, but down the line, it might help the moving on along for all parties. On the flip side, when you defer to excuses, especially ones so ingenuine they can tell, it only makes them feel patronized and/or stupid.

18. Ending a commitment with a nicely worded text

The operative word here being nicely worded doesn’t change the fact that texting isn’t the best way to end a committed relationship. There are exceptions to this rule, of course, including distance or if breaking up in person might pose a threat to safety, like in cases of abuse.

However, if things end on a less toxic note after years together, and all they get is a text reading it’s over despite being physically within reach, that’s just rude and honestly unfair.

19. Not being there for your biggest fan in their most difficult time

Supporting each other is one of the very tenets of a healthy relationship, right up there with communication, intimacy, respect, and the ability to make each other laugh. While it’s not right to do something for your partner in hopes of getting it reciprocated in the future, they say one good turn deserves another.

I don’t imagine anyone would take kindly to their significant other pulling a disappearing act whenever it’s their turn to be supportive. Nor should they. Even in non-romantic relationships, the closer the person is to you, the more readily you would move heaven and earth for them, the more painful it gets when they disappoint.

20. Acting like what you had was just another regular for you

If I considered something special (a significant source of happiness to me) and then have that feeling invalidated by the other person’s apathy, it would sting more than a little bit. Even if it’s just the memory of it you see them refer to offhandedly, it’d still hurt.

Now, this can manifest in any form, like when an ex or a good friend leaves town without saying goodbye. Or when a love interest who gave you so much hope for a future together ghosts or fades, only to return and casually treat you like every other person. No remorse, no explanations, just vibes.

21. Being perpetually sad around them but happy literally anywhere else

If you’ve ever been in love with someone who was extremely sad all the time, you must be familiar with how out of the water it feels. You struggle with everything from finding the right words to techniques you never knew existed just to cheer them up – all to no avail.

Now that helplessness can metamorphose into hurt when you see them brighten up around other people who don’t put in half the effort you do. It’s a particular kind of pain knowing you can’t very well hope your person stays sad, even as your heart sinks deeper every time someone else brings them the spark you fail to.

22. Having a friend or relative break the news

We’ve already established that the breakup conversation is an uncomfortable one at best, irrespective of how you go about it. But of all the ways to end things, doing it through a friend, relative, or any other third party has to be one of the worst.

No amount of tact the deliverer applies can mask the ridiculousness of getting them involved in the first place, no matter how close they are to either party. A close second would be to do it in public, where they couldn’t possibly express themselves as freely, just to avoid the awkward part.

23. Breaking up with them on a special occasion

Intentionally breaking up with someone on a day they deem special is as good as saying you never loved them, not really. It’s why holidays, birthdays, weddings, graduations, or more specifically, valentine’s days are some of the cruelest to decide to end things.

By doing that, not only do you risk ruining their day, but you also damn them to nursing a broken heart/remembering old wounds every time the date comes around. On the flip side, it might be the best way to go if you want to break up in a manner you don’t want them to ever forget.

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In Conclusion

The ideal breakup isn’t encapsulated in false hope, promises, and sweet words to avoid hurting someone or making them cry. The hardest thing to do is to close the door on a relationship. 

If you can’t end things effectively without breaking someone’s heart, the best you can do is try to ensure they can pick up the broken pieces afterward to help them heal and not feel lost. In other words, don’t traumatize them if you can help it. But if you must, above is an assortment of the cruelest possible ways to get rid of your last relationship.

I hope you enjoyed the article. Been there, done that? Share your unique opinion/experience along with your feedback in the comments and share the article if you liked it.