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GOIN' IN FOR THE PINEAPPLE

Euphemism for daring to do something preposterous, potentially amazing.
The calculations are solid, bruh. You might think I'm crazy, but I'm goin' in for the pineapple.

Taking the Pineapple 

Origin: Australian Army.
A phrase used to describe being assigned a rather shitty task and having no other option but to undertake said task. Usually used in conjunction with BOHICA.
"How's it going mate"?
"Fucked. I've been taking the pineapple all day"
Taking the Pineapple by CHA429 January 8, 2009

Pen Pineapple Apple Pen 

A groovy song about pens, pineapples, and apples.
Referred to as "Gangnam Style #2"
Person 1: Apple pen. . .

Person 2: Pineapple pen. . .
Together: EUGH, PEN PINEAPPLE APPLE PEN!
*Groovy Music*

Harrogate Pineapple 

A Harrogate Pineapple is an indescribably twisted sexual practice offered as a special service in the darkened backrooms of some of the most refined and elegant-seeming tea-rooms of North Yorkshire, in the United Kingdom.
"Could I order a pot of Darjeeling, a tray of small cakes, and... er... the Harrogate Pineapple?"

"I'm sorry sir, this is not that sort of establishment. Please leave, before I have to call the Army"

GOIN' IN FOR THE PINEAPPLE

Being brave enough, visionary enough. to attempt something extraordinary.
He's way outta my league, and he'll probly hard pass, but I'm goin' in for the pineapple.

who lives in a pineapple under the sea 

The first line of the Spongebob Squarepants opening theme. Also a pretty dank meme.