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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