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Entertaining someone 

When you entertain someone it means you give attention, please, laugh with and/or flirt with said person.

You shouldn’t entertain other people that aren’t who you intend to be with.
Look as Greg over the laughing and flexing in front of that girl he’s entertaining her but has a girlfriend .

Josh shouldn’t be Entertaining someone else while with Katie

Entertaining 

Spending time with a person romantically who is not your boyfriend or girlfriend.
Tonight I am doing some entertaining! Sam is coming into town.
Entertaining by 2341 November 3, 2008

Mildly offensive, highly entertaining 

Sometimes distasteful, irritating, unpleasant, repugnant to the moral sense, lacking class/good taste/grace, uncouth, or disagreeable to some; but extremely amusing, interesting, humorous, or hilarious to most.
Person A is causing a ruckus and being outlandish in public.

Person B: "That guy sure is a mess, but it's really funny! What he's saying would surely be offensive if I actually cared."

Person C: "I'd say he's mildly offensive, highly entertaining."

Entertaining 

when white people have company over.
This apartment has an open floor plan which is perfect for entertaining
Entertaining by ScreemingIntrovert September 19, 2015

Entertaining Welsey Shaw 

A witty, well-written novel by John Grabowski that for some reason is called "Entertaining Wesley Shaw" for some reason. Please note it's "Wel-sey," not "Wes-ley."
Entertaining Welsey Shaw is a witty and clever contemporary novel that will make you laugh.

Entertaining 

Describes a person, place, or thing
When your homeboy calls you to say your wife is stepping out on you with another dude but, he cannot tell you who the dude is because nine times out of ten your homeboy is the one entertaining your wife and vice versa
Entertaining by REALIST2307 April 22, 2011
More from Urban Dictionary
The phenomenon where adults salivate at children's toys
Every time I walk into the toy aisle, I catch myself kidulting over the latest action figures and LEGO sets!
kidulting by Emotional Cruiser October 12, 2025
Word of the Day on October 4, 2026
British slang for a scientist or technical expert, esp . when the speaker is not certain of the expert’s specific field of study. Not necessarily derogatory, but typically used by persons without a technical background. In the US, the equivalent would be “egghead”, “squint”, or “geek.”

Origin of the word is unknown. Started sometime in World War 2. Given the typical evolution of British slang, could easily have started because what these experts did was confusing or “baffling” to the common person.
According to the boffins downstairs, the murderer used a serrated blade.
Boffin by Agnon February 11, 2023
Word of the Day on October 3, 2026

Pee Calculus

When you have to pee in a movie but don’t want to miss anything, and must do the following mental equation: will the amount I have to pee cause enough discomfort to diminish my attention capacity for the remainder of the movie to an extent which is greater than the amount of the movie I would miss by making a mad dash to the restroom.
I saw Satantango last night, wonderful film but by the 5th hour I had to start doing pee calculus.
Pee Calculus by anorlondo October 1, 2026
Word of the Day on October 2, 2026
Literally "dirty" pronounced with a West Indian accent. Can also have a positive connotation, for example Sean Paul's album title "Dutty Rock".
"The girl is pretty but she corrupt and dutty!"

or, in a positive usage:

"Booya! That freestyle was dutty!"
Dutty by J Hall April 3, 2003
Word of the Day on October 1, 2026
korean word for madam, older woman
Ajumma wait a moment
Ajumma by aintnotinbutnice July 5, 2009
Word of the Day on September 30, 2026

Slop Grenade

When someone uses AI to generate a large document, slide deck, or piece of code/software and tosses it over the fence for you to deal with.
Chad: Hey Brent I sent you the new backend API change to review, it’s only 100 files changed.

Brent: he just tossed me a slop grenade
Slop Grenade by Joe Squid September 28, 2026
Word of the Day on September 29, 2026
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