re: Workplace: Should I take the L?

First of all, no self-respecting adult man should ever “loan” twenty dollars. That trivial amount is always a gift. No strings attached. I believe this extends all the way up to $500 or so…but can understand it could be lower to some, such as $100. Anything lower and you just simply can’t afford to gift or loan money because you’re just as broke.

Secondly, any self-respecting adult man who happens to receive such a “gift” should always return said favor at the earliest opportunity. This could be giving that amount directly back, buying a meal, taking a turn to buy something else, grabbing the next round, bringing in donuts to the office, whatever, etc…

This just serves to distinguish who is a respectable man and who is a POS loser. Let the chips fall where they will. You don’t need to call out the guy because he already knows it, and so does everyone else.

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Take the L and never loan him money again

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Ding Ding

Take this to heart because he will ask you again. He thinks you're a mark now.

Dude is clocking you

Knows he can con you and is also seeing if you’ll come at him about it.

Be prepared for more shenanigans from ole baw.

He’s clearly winning

You got off cheap and learned a lot about the dude. Money well spent. Take the L with a smile.

I was going to post that clip

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I can't believe this is even a serious question. 20 bucks? You are presumably a grown arse adult dealing with someone much younger that apparently has a shitfest of a life anyway. And not only that you didn't even "loan" him the money, you gave it to him with the full expectation that it was gone from your pocket permanently.

Asking for it back because you didn't get a shitty tailgate dip is just mega strange.

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You're not one for accountability I see. This is about character, not $20.

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His nickname going forward is “20”. So he is reminded he is a POS everyone you interact.

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I'd go with:
Two O or Andy (for Andrew Jackson)

You let him hold a $20

For the record... he never asked, on Wednesday I asked him what he was going to bring to the potluck, he said he wanted to make his dip but didn't have money for the ingredients (we got payed that Friday)... the issue isn't the 20 dollars, it's that he used it to put gas in his car... I did ask him last Thursday how he thought he was going to get to work if he didn't have my money to pay for his gas and he said he was going to ask his sister. I have only seen him in passing at work since then because he is back working on the manufacturing side of the building... and no he doesn't seem bothered by what he did because he is still trying to make small talk and tell jokes but I have been pretty short with him so far. I think he just grew up in such a shite environment that he saw his "parents" do stuff like this and feels it is no big deal... lesson learned about his character.

Make a big batch of buffalo dip for the whole crew to enjoy, but don't let him have any.