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A saying that some people have that are rebels against society like biker gangs, heavy metal bands etc.
Jess James was an old west outlaw that robbed hundreds of trains and banks.
Man 1: Lets drink ti Jessy James.
Man 2:Yeah,God bless Jessy James.
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This can be an insult, an expression of pity/sympathy, or even a compliment, depending on the context. As an insult, it can mean a variety of things, ranging from "what an idiot" to "f*** you". In a more sympathetic way, it can mean something to the effect of "I feel bad for you/so-and-so" or "what a shame". As a compliment, it can actually mean "what a sweetheart" or "how cute/sweet". In that sense, it's typically referring to someone's innocence or as a term of endearment.
Examples of "bless your/his/her/their (little) heart(s)" in typical conversation:
Insult (what an idiot):
"His boss told him if he made another careless mistake when filing the data reports again, he'd fire him on the spot. Bless his heart."
Insult (f*** you):
"Hey baby, you've got to be the sexiest little thing here. How about you and I head back to my place and throw our own private party?"
"Bless your little heart. Thanks, but I think I'll pass."
Pity/Sympathy (I feel bad for you/so-and-so):
"Bless her heart, she worked so hard to bake a nice cake for her mom's birthday. But she tripped while carrying it and it was ruined when it fell on the ground."
Pity/Sympathy (what a shame):
"He could have been top of his class, if he hadn't started started skipping class to hang out with those troublemakers. Bless his heart."
Compliment (what a sweetheart):
"I don't know how she finds the time to raise those kids, clean her house, work as a part time substitute teacher, volunteer for church events, and still host occasional social gatherings in her home. Bless her heart, she's a saint!"
Compliment (how cute/sweet):
"Look, mommy! We made macaroni art at school today! Do you like it? I made it just for you."
"Bless your heart, you're so thoughtful. I love it! We'll put this on the fridge for everyone to see!"
An Irish blessing is when you get cursed out by someone (usually for messing up).
Jonathon messed up so bad, Marc gave him an Irish blessing.
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A bro's blessing is the highest honor a man can give his friend, it is an oath to help your bro through anything he will face regarding what you blessed him for, usually for success with a woman.
Bro 1; Yo, I\m boutta ask this girl out.
Bro 2; I give you my bro's blessing for success
To be thankful for the love shown, great friends, and friendly reminders that people care.
I’m grateful for the birthday blessings I was bestowed and the loved one close I hold dear.
A term used to insult a person based on their looks.
John: Ew Amy looks terrible; kind of liked blessed cheese
In the southern United States, “Blessed” means ”God loves me more than he loves you”
Blessed that I went to Disney World and all you did was take a trip to Walmart.