Okay, I did my best. Better than before and thanks for the help Elmer!
I can’t speak for others, but I select images that lose most of their meaning and inspire humor when stripped of context. My problem with photos from current events and politics is that all the jokes have already been made and propagated all over social media.
Okay, dudes- funny captions for that cat.
(Look, I know it isnt the best, but I will do better)
Work from home: I’m nude from the waist down.
The single best rule for what images to post is “funny”, with “weird” and “baffling” 2nd and 3rd.
Essentially you need to be able to post a link in the form of “http:/www.blahblahblah.jpg” for Discourse to preview that picture. When you’re more comfortable with posting links there are sometimes ways of getting at the address of graphics on sites where right-clicking the image doesn’t directly give you a postable link. (By using a page editor to dig out that site’s internal link to where it stores graphics).
I did “funny”, next time I will try the others.
Back to the contest!
“As head of HR, we want to find an equitable outcome for everyone; just sign here.”
"What I’m mostly looking for in the home of the family that adopts me is black upholstery. Lots and lots of black upholstery. "
Not in play: That’s a very good photo for this contest.
“We can sit here all day, but I still don’t know how your favorite dress got shredded.”
And once again, Colin’s kid left the Zoom cat filter turned on.
Jeffrey Toobin figured that with the Zoom cat filter on, if he got caught wanking onscreen again, no one would know who he was. If only he’d remembered to delete his name…
Blofeld never suspected that Mr Fluffypants would one day stage a coup and take over SPECTRE.
I’ll bet you’re wondering why I called you here.
Lumpy, you win! 
You are up!
Not in play, but today happens to be the anniversary of the O.J. Simpson slow speed chase.
I think it works as a caption.
Looks like I’ll be late for diner again!
“Line up and wait” taken to an extreme when the President decides that nobody can operate a motor vehicle while he plays golf.