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According to one study by Gilovich et al., published in Psychological Review, some regrets will heal over time, but others will be less likely to.
There are two types of regret: regrets of commission and regrets of omission.
Regrets of commission are regrets about things you did, while regrets of omission are regrets about things you did not do.
Guess which ones we regret for the longest time?
That's right – we regret the things we don't do for longer and in fact those regrets tend never to heal (personally I have some episodes in my life that I still wondering "what if"). This seems like a clear message to 'grab life by the horns' as it were and to 'do more stuff', but again it's probably a little more complicated than that…
The reason we regret the things we don't do most is that we never find out the possibilities outcome. We have an idealized version of how those things would have turned out in our heads so we regret not living that possible reality. Meanwhile, the things we did do we got to see in the cold light of day – thus they tend to be considerably less interesting.
You may have done many other miraculous things your life – whether that's getting married and having children, being there to support your family or winning the Nobel Peace Prize… the problem is that you know what that was like and it was imperfect.
Thus the 'undone' things always seem more interesting. Likewise the mistakes you make you live through and so you decide they could never have been that bad.
What you also must realize is that it's actually completely required that you do turn down some of what life has to offer. Very often in order to experience one thing we must necessarily turn down something else. There are billions of options open to you every single second and yet you will always just choose one of them. That's an infinite undone-to-done ratio.
This might sound depressing – as though you'll never be happy with what you decide – and it's very much a case of 'the grass is always greener'. But in reality, the grass always seems greener on the other side. It's not, and what you've done is probably perfectly remarkable and worthwhile in its own right: you just have to learn to see that.
If you can reframe the way you look at your roads 'untaken' then, you might find that you can overcome that feeling of regret. But would they fade over time as time went on even if you never managed this, or does the study prove that they will never go away?
To be honest, the research seems to suggest that our regrets won't completely fade – and particularly when they're related to things we didn't do.
Let's take an analogy from a story entitled "Mistakes" by Vsauce sources A friend told him that past mistakes were like carvings in a tree. They don't grow with the tree – they don't even get higher. Nor do they tend to fade and in fact, in some cases, they can get darker. However, while the marks don't change, the tree does and over time it grows to become significantly huger leaving the marks as a relative 'dot' in the bark. In other words, the carving that once took up a big proportion of the tree is now just a tiny mark on a huge tree – just a very small part of that tree's history.
Your mistakes are similar. They might not go away, but as you build on them and have more experiences you will find that you can bury them. They're a part of who you are and actually you shouldn't want that any other way – however, they are an increasingly insignificant part of who you are. The key is to accept them and grow anyway.