Workplace: Should I take the L?

This is long... DV or don't read if you do not want to...

I am a shift leader in a warehouse. We hired a 26 year old machine operator about a year ago... nice enough kid but always seemed like he was everyone's "bro", I kept my distance and always interacted with him in a professional manner. A couple months ago our boss/manager sends him to the warehouse side of operations for him to be cross trained, I am in charge of training him so naturally we shoot the shite and he tells me about his life... grew up in a shitty situation, has never filed his taxes... has had many jobs and then just found out he has a 5 year old son he never "acknowledged" or in his words "knew" about. The only way he found about his son is because the mom left the kid in the car at a wal-mart during the winter and it was court ordered he take a paternity test and sure enough he was the father... so now he just started getting dinged with 300$ child support payments every paycheck (twice a month) so he is really complaining about being broke all the time... mind you he has a 2022 car he bought last year that his younger sister co signed for and he gets door dash delivered to work almost every night... he has razzed me à few times about driving a shitty car and I just laugh it off and tell him it's nice not having a car payment.

HERE IS THE STORY: We had a 4th of July potluck last week for Thursday evening, I made Lil smokies and he said he wanted to make some buffalo chicken dip but was broke and did not have the stuff to make it but wanted to... so being nice I fronted him à 20 dollar bill and told him to make the dip and don't worry about paying me back... well he shows up Thursday afternoon with no dip or nothing and I confront him about it and he says he needed to put gas in his car and im like your serious dude but let it go for the time being... well we had our pot luck and he proceeded to pig out on everyone else's food like nothing even happened!!!

Would you ask for the money back and possibly make drama at work over 20 bucks or just let it go? I am not a manager but am one step below so I don't know how this could be thought of... Right now I am leaning towards letting it go but F being nice or lending somebody money ever again!