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Caulk the wagon and float it

To take your time and be cautious when crossing rivers, but also not so cautious that you will only cross a river if there is a ferry present.

Originally a mindset used in the classic computer game The Oregon Trail, but can also be a way of life.
Don't be foolhardy and just try to ford the river. Take your time, be cautious, caulk the wagon and float it.

Caulk the wagon and float it

to stick your dick in a girl doggy and then pick her ass up and bounce it on you
dont bend your hips, dont ask her to do it; just caulk the wagon and float it.

will it float 

A recurring segment on the Late Show with David Letterman where an item is presented and Paul and Dave take guesses at whether or not the item will float or sink in a large pool of water.
It's time for another round of Will It Float, people.
will it float by Athena Kay May 10, 2005

Do it float?!

Do it float?! by DoItFloat? March 26, 2010

will it float 

Recurring segment on Letterman
David Letterman: What are we playing for tonight, Alan?
Alan Kalter: Dave, tonight we're playing for a brand new monkey!

let it float in the river 

When you let someone or something go which you know will make you cry later but it's the best for you
I liked him for nine years but he had a girlfriend so, I let it float in the river.