Especially when you know he or she is on the self-loathing, personal disability, or a total lack of appreciation for your hidden joys.
And yet, in this world where everything is recorded by a social network (and / or government), there are parameters that makes the most acute pain.
As the University of California, Santa Cruz study found, Facebook can make a break up even worse.
It seems that even when we started the sidewalk with more unfair that Turkmen election we struggle to erase our digital memories.
As reported by the Daily Mail, even if half of the respondents said they would immediately get rid of all digital recordings of a love gone wrong, even they regret. A third party can not press the delete button on all their digital memories.
How on earth can we get rid of these romantic shots in the mountains above Las Vegas - those where love seemed to rise above the heavens? How can they destroy slightly tipsy pictures of hugs, silly faces and long lazy days on the beach? And then there are the nude photos.
They all chronic something that would have been great form, but was marred by the interference of family, friends, career - or temporary insanity.
The Mail quoted Steve Whittaker, a Santa Cruz, UC professor of psychology: "There has been little exploration of the negative role of digital assets when people want to forget aspects of their lives."
Well, researchers have been too busy recording the negative role of digital goods when people do not want to forget aspects of their lives. Whittaker and his co-researcher, Corina Sas Lancaster University in England, realized that digital memories are now required on all kinds of devices of all kinds of shapes.
There could be videos and photographs. There could be the Facebook messages, texts and tweets. But there are also e-mail you when it described as his "hero par excellence."
How are you supposed to remove it? It might not be talking to you now, but once that anyone of you could come back. And then what? You're supposed to start all over again? It's just too much work.
And if she comes back and discovers that you have everything removed, she could never forgive you.
All this is compounded by the fact that we spend so much of our lives in digital spaces. Our noses and minds are in phones and laptops. The state of our hearts is often displayed on a hourly basis.
Although the sample of this research could hardly be called significant (24), which dragged like a parched tongue, is that it was undervalued were most reluctant to remove their immediate past and loving.
The most painful moment is, it seems, the change of status to "single." This is where the shame and pain entwine their legs around each other.
For many, the happiest relationship, there is evidence of more digital joy and glory.
This means more to remove. And worse, than can not be deleted.
On Facebook, for example, you may choose to delete your past. But if others have re-posted your updates, they still exist on their cash flow and all those who could spread further.
If your name has been identified, it is the digital equivalent of a permanent tattoo.