TL;DR It is better to believe that it is better to have loved and lost, than never to have loved at all

Love need not be a tempest; in tragedy or ecstasy-or overflowing, reaching, stretching. To memorialise it by imagining it as this towering monument in our history surrounds it with a sort of legend; which shields us from its sharper points and jagged edges. It’s a blessing or a curse. There are some things which are better and safely forgotten- there are other things that need to be remembered.

They’re worth remembering because having lost something once does not mean that you’ll never love again. It does not mean that had you not had that experience, you’d never have loved at all. It doesn’t mean that it would be better if you hadn’t loved to begin with. These are all things which can be lived through, although it mightn’t be easy. The past is fixed and we can’t elect not to remember it: it might be better to just believe that it was worth having just to lose than to try to imagine the infinite other paths that could have been taken. Ultimately, all that really matters is whether it’s better for you to believe it or not.

A bad lover can leave you with trust issues after cheating, deceit, emotional abuse, etc. Not everyone you fall in love with will leave you with a great experience.

Such trust issues can ruin your next relationship as the failure to trust is usually a one way ticket to a failed relationship. This cycle is then hard to break, showing how some lovers are better off avoided.

In his poem “In Memoriam A.H.H.,” Alfred, Lord Tennyson wrote:
I hold it true, whate’er befall;
/
I feel it when I sorrow most;
/
‘Tis better to have loved and lost
/
Than never to have loved at all.

The poem is an elegy about grieving the loss of a close friend and taken out of context, it shows that love spans massively. To uncover the mystery proposed and the question implied in this statement, I want to leave the statement in the context of the poem. The poem goes on for 131 lines and was written over many years. Not only does it show a development of Tennyson’s emotions, but it shows his exploration of them.

While the poem was being written in smaller cantos, Tennyson thought he couldn’t accurately express his emotions. There is an obvious focus on the structure of the poem, especially in Canto 27 (the one above!). Rhymes at the end of the first and last line with near rhymes in the middle two lines. Okay, sorry for the fluff.

What I’m getting at here is that the poem was written as a potential consolation for Tennyson’s own self and readers are meant to acknowledge it on these terms. It’s difficult to translate – that is, the statement and personal grief as a whole. The source below doesn’t get into Canto 27, but it grapples with love and loss as a concept throughout the poem and states, “In fact, it might even be argued that this is one of the poem’s merits: the reader is not made to feel a part of Tennyson’s grief, merely a witness, forced to contemplate the incomprehensibility of individual human consciousness…”

“It is better to have loved and lost, than to never have loved at all” is an example of the “incomprehensibility of individual human consciousness.” There’s a certain passivity to the statement and it’s hard to empathize with, but also hard to agree or disagree with because it doesn’t feel complete. It implies loss no matter what – the experience of losing with love or losing love. “At all” though? Really? It’s nearly unimaginable.

Happy Choosing!

https://thegsaljournal.com/2020/05/19/the-articulation-of-grief-in-in-memoriam-a-h-h/

I have to question if the people agreeing with this have ever felt grief or heartbreak over a loved one before.
I can't fathom how anyone can go through that and still claim that it was worth it.

I think this question is very dependent on whether you see the glass half full or half empty. In the short term it can be terrible, grief and heartbreak are horrible feelings, but a necessary part of growing stronger in the long term.

My position is that I believe it is better to have loved and lost than to have never loved at all because you can always learn from every experience... and as long as you take the right lessons from each situation then you will always be growing and becoming a better person.