UPJOKE
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A man has the opportunity to win a million dollars if he can cross lake Superior in a 16 foot sailboat...

The people sponsoring the challenge give the man two choices of what he can bring on the boat to assist him. He can either bring a large box of novels or two criminals. However, the people running the competition get to choose what the books are and who the criminals are.

The man realizes the...

What did the chihuahua name his sailboat?

El Barko

What Do You Call Someone Who Argues About Sailboats?

A Mast-Debater!

What happens to a sailboat in a category 5 hurricane?

MAST DESTRUCTION!!!

I'll ~~see~~ sea myself out...

What did the ocean say to the sailboat?

Nothing. It just waved.

The banker fell overboard from a friend's sailboat.

The friend grabbed a life preserver, held it up, not knowing if the banker could swim, and shouted, “Can you float alone?”

“Obviously,” the banker replied, “but this is a heck of a time to talk business.”

What do Sperm Banks and sailboats have in common?

Practically nothing

I don't trust sailboats

They're rigged

A 60 year old man named Bill goes to get his physical.

When his doctor is finished, he shakes his head. "Bill, you're a 60 year old man, you have the body of a guy in his 40's. You're in better health than most patients I see. I have to ask - how old was your dad when he died?"

"WHAT?", Bill bellows, "Who says Dad's dead?" The doctor starts t...

This joke may contain profanity. 🤔

Introducing a new joke style: I wish all the ladies

This was a thing we used to do on my sea scout ship after competition. It's a rhyming couplet in the general style of

"I wish all the ladies
Were [XXXX]
And I'd be [YYYY]
And [sex pun]"

A few examples:

I wish all the ladies
Were winds on the sea
And I'd be the sa...

Helsinki

My uncle was in a race across Europe. He was in first place for a while and got to the edge of the Baltic Sea and saw some sailboats drydocked by the water.

He might have been a little too presumptive when he was pulling a boat to the edge of the Sea. The boat’s owner came over to him. He wa...

Sail on, sailor

Man to his wife: "If I died before you, would you remarry?".
Wife: "Oh well I'd have to think about it but yes, I probably would."
Man: "Would you stay in this house?"
Wife: "Well, it's a nice house dear, I think I would"
Man: "Would you sleep in this bed?"
Wife: "I like the bed, it's...

The Orphan

A boy was living happily with his brother, mother, father, and dog. His father worked in a factory. The pay was ok, but the work was hard. One day, a man knocked at the door of the family. The man sat them down and informed them that the father had been caught in some machinery and had died. Th...

God will save me.

A man is living in a house when a dam breaks and a violent flash flood happens and hits his whole neighborhood. The water begins rising higher and higher every moment. He's standing outside knee deep in water when some people on a canoe show up, they say to him "Hurry, get onto our canoe and we'll...

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