“Sometimes you break your heart in the right way, if you know what I mean.”

“Sometimes life, will get you down, break your heart, steal your crown.”

Tom Petty (1950–2017) American musician

“I tell you this
to break your heart,
by which I mean only
that it break open and never close again
to the rest of the world.”

Mary Oliver (1935–2019) American writer

“I know that it will hurt
I know that it will break your heart
the way things are
and the way they've been
and the way they've always been”

Natalie Merchant (1963) American singer-songwriter

“And I know it aches
And your heart it breaks
And you can only take so much”

Bono (1960) Irish rock musician, singer of U2

“Sometimes it's not enough to know what things mean, sometimes you have to know what things don't mean.”

Bob Dylan (1941) American singer-songwriter, musician, author, and artist

“Clarity is of no importance because nobody listens and nobody knows what you mean no matter what you mean, nor how clearly you mean what you mean. But if you have vitality enough of knowing enough of what you mean, somebody and sometime and sometimes a great many will have to realize that you know what you mean and so they will agree that you mean what you know, what you know you mean, which is as near as anybody can come to understanding any one.”

Gertrude Stein (1874–1946) American art collector and experimental writer of novels, poetry and plays

“Break my heart? Is that what you just said? I have news for you; you didn't break my heart. My heart's fine. My heart's in the best shape of its life. You know what you did to me? You took an AK-47 and blew my soul open.”

Tiffanie DeBartolo (1970) American writer

“It doesn't matter what people thinks of you as long as you know that your heart and head are in the right place.”

Steve Kluger book Almost Like Being in Love

“And if my mind breaks up
In all so many ways
I know the meaning of
The words, “I love you””

Cat Stevens (1948) British singer-songwriter