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Squishy Pineapples

Clenching onto a male's balls and squezzing so hard they pop.
My girlfriend told me if I dumped her, that she would gove me "Squishy Pineapples".

Define pineapples

Something only a retard would ask urban dictionary to do
Retard: idk what a pineapple is, so I'm gonna ask Urban Dictionary to define pineapples
Define pineapples by NetPie January 14, 2017

picking pineapples 

Me: Hey wyd
You: picking pineapples

Catching Pineapples

Opposite of 'low hanging fruit' in management speak, intentionally dealing with the difficult/awkward stuff first
I've been busy catching pineapples all day Jon!

Purple Pineapples 

When you tie a rope around a woman's breasts during BDSM play. Tying the rope tight enough causes her breasts to turn purple.
Guy 1: Dude what'd you and Sarah do last night?
Guy 2: Dude she let me give her Purple Pineapples.
Guy 1: Sweet.
Purple Pineapples by Zon157 May 21, 2020

Box of Pineapples 

A term of comparison or description of a person or group who appear(s) to be largely unqualified for the task they are preforming.
You'd be better off to replace the bean counters with a well trained box of pineapples and some slide rules.

I sent a box of pineapples to the supply closet half an hour ago and they just came back with a mop. We have carpeted floors.

The IT team is basically a box of pineapples with opposable thumbs and a knack for losing passwords.
Box of Pineapples by Frank Shelly November 26, 2018