Heartbreaking Jokes - 16 Hilarious Heartbreaking Jokes

Heartbreaking

Dallas Morning News - A 15 year old boy was at the center of a Dallas County courtroom drama yesterday when he challenged a court ruling over who should have custody of him. The boy has a history of being beaten by his parents and the judge initially awarded custody to his aunt, in keeping with chil...

A man's wife dies young

The funeral is heartbreaking. The poll bearers pick up the casket and are moving through the hallway of the funeral home when the casket hits a corner and opens, the body falling out. Miraculously the woman stands up, alive and well!

40 years later, the wife dies again. The funeral is heartbr...

My brother who has a stutter is in prison.

It’s just heartbreaking knowing he will never finish his sentence.

A fortune teller told me I'd suffer a tragic heartbreaking loss in 12 years

So to cheer myself up I got a puppy

The most heartbreaking thing to ever happen to me.

I was about to propose to my girlfriend one night when my housemate Joseph barged into the room out of nowhere. He tripped and fell over, breaking a glass table with his face. Now I didn’t know Joseph *that* well - hell don’t even remember where he was from, but I managed to suppress my frustration ...

What's heartbreaking but heartwarming at the same time?

A flaming arrow to the chest

I met my daughter's teacher tonight, and it was heartbreaking.

She was working at her second job. Teachers are among the most underpaid and undervalued people on Earth.

I decided to give her $50 for a lap dance, so I'm doing my part.

I am so addicted to junk food...

...it's heartbreaking!

The English team visited an orphanage in brazil.

"It’s heartbreaking to see their sad little faces with no hope”,said Jose age 6.

Have you heard about that new virus that is devastating the bird population?

It’s called Chirpies.

What’s most heartbreaking about it is that it’s...

untweetable.

I had to do a dissection today.

It was heartbreaking.

England players visited a russian orphanage yesterday ahead of the world cup...

''It was heartbreaking to see their little faces with no hope'' said Vladimir aged 6.

This joke may contain profanity. 🤔

A man taking a walk along a pier...

... suddenly hears this heartbreaking sobbing. He goes to investigate the noise and finds a woman in a wheelchair, without arms or legs, crying her eyes out.

He rushes over and kneels down besides her, asking her if she's ok, has she been abandoned here?

"Well," She answers, through he...

Loooong, but maybe worth it.

A woman is pregnant in her teens...finally gives birth to two healthy twin boys. She’s young, and destitute, and knows she can’t take care of them or provide for them, and after a bit of soul searching she makes the heartbreaking decision to give the two boys up for adoption. Over the years she kept...

The magic mirror

Some say that there is a magic mirror in a shopping ladies room that could grant any wish if you tell it the truth, but will make you disappear if you lie in front of it.

Once there was a beautiful brunette that found this mirror and said:

- I've been thinking a lot and I think I'm the...

This joke may contain profanity. 🤔

A man with a lisp went on a blind date to a heavy metal concert

Paul had been ridiculed all his life for having a lisp. As a kid, he was bullied in school. As an adult, he caught coworkers making fun of him when they thought he couldn't hear. He would even notice cashiers trying to stifle their laughter. No woman would ever go out with him, and he felt resigned ...

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