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shake the tree until they all cum out. 

A sex phrase that involves masturbation or sex with a woman.

it means you stroke your dick until all the semen shoots out.
12 year old: I cannot cum, but why?

Sex obsessed person: Well, you gotta shake the tree until they all cum out.

Shake the money tree in a wine cave 

Fancy political fundraisers for rich donors. In 2019 photos surfaced in which Pete Buttigieg, mayor of South Bend, IN was seated with rich donors in a Napa valley wine cave for a fundraising event. During Dec. 2019 debate, Elizabeth Warren attacked Buttigieg for appealing to rich donors instead of grassroots supporters by using this imagery. A few minute later, Andrew Yang stated his campaign reform policy would increase women and minority elected to offices around the country because "they don't have to shake the money tree in a wine cave", gesturing to Buttigieg.
You will have many many more women run for office because they don't have to shake the money tree in a wine cave.

hit the shade tree 

Usually means you're fired from your job.
Joe: Sorry I'm late again, I had a flat tire.
BossMan: Hit the shade tree!!!!!
Joe: "sits under tree"
hit the shade tree by Jojwjwjejej December 27, 2013
More from Urban Dictionary
The number of years you are still sexually active
While our lifespan is the number of years we will live, our healthspan is the number of healthy years we will have and our sexspan is is the number of years we will continue to be healthy enough to continue having an active sex life.
sexspan by Dr Kat April 21, 2022
Word of the Day on October 28, 2026
A lighthearted reaction upon receiving disappointing news of some sort. Usually something that isn't a particularly a big deal, esp. when it primarily affects someone else - sort of a mild schadenfreude. Sometimes doubled or tripled, and possibly said in a sing-songy voice for added comedic effect to imitate a muted trumpet, which is how the meme originated.
You didn't get any napkins with your takeout pork fried rice? Womp womp.
womp by 175623226 November 3, 2011
Word of the Day on October 27, 2026
When your wife’s boyfriend let you sleep past 8pm 😎😎
Wife’s boyfriend: You have 5 more minutes
Me: Poggers!
Poggers by Just_Charles April 14, 2020
Word of the Day on October 26, 2026

Oblication 

A vacation, feeling more like an obligation, that involves visiting or staying with family.
So Joe where are you taking the kids for spring break vacation? We are going on an oblication to Boca to visit my mother-in-law.
Oblication by kimmerr May 5, 2011
Word of the Day on October 25, 2026

Surf Dracula Syndrome 

A phenomenon in film/television series, most notably streaming series, where the main premise is drawn out to such a point that it takes an entire season or more to get the parts of the series the audience is actually interested in seeing.

For example, if a series is titled "Surf Dracula," a majority of viewers would tune in expecting to see Dracula surfing by the first or second episode. However, the entire first season would instead be tedious padding and backstory before finally ending with Dracula surfing in the last five minutes of the season finale.
I watched "Smallville" on Netflix the other day. Dude, it was ten seasons of filler before he finally flew! Major Surf Dracula Syndrome!
Word of the Day on October 24, 2026

Northstarring

Finding your way back to the truth by fixing on one verified fact and working out from there, the way you navigate by the North Star when everything around you is spinning.
Rumours were flying everywhere, so she went northstarring — one checked fact at a time.
Northstarring by Light Bearer October 22, 2026
Word of the Day on October 23, 2026
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