Funny Heartbreak Quotes & Sayings

It was funny how heartbreak turned into great art. — Jennifer Probst

As a kid my heart would break for the villains. — Criss Jami

Funny thing about guilt: There's nothing so bad that you can't add a little guilt to it and make it worse; and there's nothing so good you can't add guilt to it and make it better. Guilt distracts us from a greater truth: we have an inherent ability to heal. We seem intent on living through even the worst heartbreak... How? ... Practice. — C. Jay Cox

Through a veil of tears I watched the city get smaller and smaller. It was funny, because it sort of felt as if my heart was doing the same thing. — E.M. Denning

Funny how easy heartbreak can come. I've always had a talent for it. — Christopher Moore

Heartbreak is funny to everyone but the heartbroken. — Jeffrey Eugenides

When he talked his eyes went away from mine and then he forced himself to look straight at me and he began to explain and I knew that he felt very strange with me and that he hated me, and it was funny sitting there and talking like that, knowing he hated me. — Jean Rhys

At some point, I figured that it would be more effective and far funnier to embrace the ugliest, most terrifying things in the world
the Holocaust, racism, rape, et cetera. But for the sake of comedy, and the comedian's personal sanity, this requires a certain emotional distance. It's akin to being a shrink or a social worker. you might think that the most sensitive, empathetic person would make the best social worker, but that person would end up being soup on the floor. It really takes someone strong
someone, dare I say, with a big fat wall up
to work in a pool of heartbreak all day and not want to fucking kill yourself. But adopting a persona at once ignorant and arrogant allowed me to say what I didn't mean, even preach the opposite of what I believed. For me, it was a funny way to be sincere. And like the jokes in a roast, the hope is that the genuine sentiment
maybe even a goodness underneath the joke (however brutal) transcends. — Sarah Silverman

There's this funny thing I've noticed about people. You never really get the story you expect. Ask them about what they have, and they'll tell you about what they want. Ask them to tell you about love, and they'll tell you about heartbreak. Ask them about death, though, and they'll tell you about life. — Pascalle Lepas

... breaking the heart of someone you still love is a rare horror, not funny to anyone, except perhaps Satan ... and even his pleasure would be spoiled by not having had a hand in it, by the dumb, wasteful accident of the thing. The Devil wants meaning just like the rest of us. — Glenn Duncan

And I think missing you hurts the most when something funny happens. Because in that one moment I find myself laughing, and within the next second I want to tell or text you what happened. And then it hits me again, every single time, that you aren't there anymore. That I lost that one thing that mattered to me. — Elisabeth Van Den Abeele