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on the sly 

To be on the sly, the active of sly. You can do something on the sly, maybe stealing something funny and legendary, like mine and Jimbo's road bollard. You could also have 'slying it'
"We took that bollard on the sly"
"Tonight we're slying it/on the sly"
"Come on lads, here we go, on the sly on the sly"
on the sly by Ybot December 28, 2005

macking on the sly 

Covert flirting between two people. Because they have to keep their true feelings for each other secret, for whatever reason (i.e. they work together, one is married, etc.).
"Those two can't seem to stand each other! They're always fighting over something!"

"Wrong, man. It's all a front they put up. They're actually macking on the sly."
macking on the sly by D. Gould March 8, 2006

Susan on the Sly 

A secondary girlfriend, one that is around constantly and annoys you and your personal friends.
Heather - Hey can I have your boyfriends friends phone number?

Girlfriend - No, he says you are a Susan on the Sly

sex on the sly

Cheating or trying to cheat when you have a spouse or significant other. Those looking for sex on the sly are liars and cheaters.
Nancy: Did you hear? Monty's lookin' for some sex on the sly. Jack saw him hit on a girl at the club.

Alice: You mean Monty, Sally's husband?!

Nancy: Yeah, can you believe it? He seemed so sweet and caring to her. Go figure.

Alice: Uh huh, another cheater.
sex on the sly by mad megawoman August 6, 2011
More from Urban Dictionary

proper lad 

a lad that is such a lad that he is a proper lad
person1:did you see bob
person2: ya he was a proper lad
Word of the Day on October 29, 2026
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
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