Should I Shame Someone Into Paying a Debt by Pretending to Be Concerned?

Some people treat a $72 debt like it’s a casual suggestion. This Reddit post is about exactly that, except the “casual suggestion” involves softball registration, a whole season, and OP covering the gap for everyone else.

OP runs a softball team for 10-plus years, fronts registration each season, then collects each player’s share. This year, a new player agreed to pay, kept showing up, and repeatedly said they forgot, asking OP to email them as a reminder. OP followed up multiple times, but by season’s end, everyone paid, except this one person who still owed $72.

And then OP did what petty people do, they looked up the player on LinkedIn, found their job, and started wondering if contacting their boss with a fake “are they okay?” concern would finally get the money paid.

Original Post

Ok so I know I should probably let this go, I don't need the money but the principle of it annoys me. I have run a softball team for 10+ years now and we always have new people join the team, every season I front the team registration and everyone pays me their portion based on how many people are playing.

This year we had a new player, they agreed to pay, and at several games kept saying sorry I forgot to pay you send me an email to remind me. They made no objection to paying their share.

But by the end of the season everyone had paid me but this person, meaning effectively with their 72 dollars outstanding the season has ended and I've paid 144 to play for the season while this person paid zero and everyone else paid 72. I've sent several emails and a text message to the person asking to be paid and it's all been ignored.

Now I know what this person does for a living, and it took me all of 10 seconds to find them on LinkedIn and see where they work. We work in the same industry and I know this person is easily making a 6 figure salary.

Their ability to pay is not in question. (Neither is my ability to absorb the cost)

WIBTA if I used some of my contacts to reach out to their boss and feign concern for them by saying hey, I've been trying to get a hold of C for a couple of weeks as they owe me for our softball fees, but they have not been responding and I want to make sure they are ok and have not had something happen?

I'm 99% sure they just don't want to pay me but this might shame them into it. Edit: Thanks everyone for the feedback, you are right there are better ways to handle this, which I should have realized.

When I came here asking for opinions that was pretty much all the confirmation I needed that it was an A move.

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It’s a lot like the sister who kept asking for babysitting, and the family member trying to set firm boundaries.

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OP’s emails and text to the new player got ignored, even after they promised they’d pay and kept blaming “forgot to pay you.”

The part that really stings is the math, everyone else paid $72, OP paid $144 total, and the only person who didn’t pay is the one who can obviously afford it.

Then OP’s LinkedIn search turns the “just pay your share” problem into a workplace leverage idea, hitting the player’s boss with a fake concern message.

So the question becomes less about softball fees and more about whether shaming someone through their job is the move OP thinks it is.

What are your thoughts on this situation? Share your perspective in the comments below.

Nobody wants to pay $72, but nobody wants to be dragged into a fake workplace concern either.

For another inheritance power struggle, read what a woman did when her estranged father demanded a share of their grandfather’s art collection.