August 25, 2026 at 7:55 am

His Coworker Keeps Giving Him Free Food and Refusing Any Repayment—Now the Guilt Is Making Him Question What She Actually Wants in Return

by Liberty Canlas

Woman holding to-go coffee cups for several people

Pexels/Reddit

Some people are so generous that they don’t mind paying for other people without expecting payment in return.

This man works in a close-knit restaurant where coworkers often pick up food and supplies for one another. A generous coworker regularly buys things for everyone and rarely asks for anything in return. Feeling uncomfortable with how much she had spent on him, he tried to repay her secretly.

This is a wholesome workplace problem where both people seem to be coming from a good place. Read the full story below.

AITA for paying my coworker back without her consent?

I (24M) work in a restaurant as a bartender with a lot of younger coworkers.

It’s a very pleasant work environment where most people are just very nice to each other.

So much so that a couple times a month, someone has to go to either a grocery store or the market to get some supplies or just goes because they want to before their shift.

This person would then ask the rest of the group if they want anything and either send a money request or not, depending on the amount or if they owe anyone.

This man’s coworker generously buys him and his colleagues food without asking for payment.

Now, one of my coworkers (18F) is an extremely generous person.

She loves to get people food or drinks, sometimes without even asking them, as she knows most people’s favorite orders at this point.

The thought behind it is extremely nice, and she is truly an amazing coworker and person.

However, my problem with this is that she never asks for money in return.

I know that at this point she has probably spent around 50 bucks at least on stuff for me alone, and it just feels unfair.

I tried to get her some stuff in return, even backed her some cupcakes, but it’s almost impossible to keep up.

He secretly paid her by putting the money in her bag.

Now, fast forward to a couple weeks ago. She would again ask what I wanted from the store. I said that I didn’t need anything.

I had breakfast at home, had lunch with me, and didn’t need anything else.

Despite that, she still got me some of my favorites, which was probably around 5 bucks worth of stuff.

I thanked her but also said, “Please take my money in return.” She said no, smiled, and moved on.

It just so happened that I had a 20 in cash, so I put it in her bag.

She found out and gave the money back to him.

She found it a week later and tried to give it back to me, but I refused.

She’s not mad or anything, but I could tell she isn’t happy about it.

Am I the jerk?

OP clearly wasn’t trying to upset his coworker and just wanted to make sure her generosity wasn’t being taken for granted. Even I would feel a little uncomfortable receiving so much free stuff from a coworker. Perhaps finding other ways to return her kindness would be a better compromise.

Let’s read the comments of other Redditors on this story.

This person shares some advice.

Screenshot 2026 08 24 at 7.49.01 PM His Coworker Keeps Giving Him Free Food and Refusing Any Repayment—Now the Guilt Is Making Him Question What She Actually Wants in Return

Here’s an honest opinion.

Screenshot 2026 08 24 at 7.49.33 PM His Coworker Keeps Giving Him Free Food and Refusing Any Repayment—Now the Guilt Is Making Him Question What She Actually Wants in Return

Another valid remark.

Screenshot 2026 08 24 at 7.49.56 PM His Coworker Keeps Giving Him Free Food and Refusing Any Repayment—Now the Guilt Is Making Him Question What She Actually Wants in Return

This one gives a different perspective.

Screenshot 2026 08 24 at 7.51.14 PM His Coworker Keeps Giving Him Free Food and Refusing Any Repayment—Now the Guilt Is Making Him Question What She Actually Wants in Return

If you enjoyed this story, check out this post about an employee who gets fired, then ends up with extra cash due to a loophole in the termination letter.

Finally, plain and simple.

Screenshot 2026 08 24 at 7.51.42 PM His Coworker Keeps Giving Him Free Food and Refusing Any Repayment—Now the Guilt Is Making Him Question What She Actually Wants in Return

The best way to repay kindness is with kindness.

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Liberty Canlas | Contributing Writer, Lifestyle & Relationships

Liberty Canlas is a contributing writer for TwistedSifter specializing in relationship dynamics, social sciences, and modern family life. Leveraging her extensive professional background in scientific research and data analysis, Liberty brings a highly analytical yet empathetic approach to dissecting viral online conflicts and social media trends.

Rather than simply reporting on internet drama, Liberty uses her deep understanding of human cognition and behavior to explain why people react the way they do. She excels at transforming complex interpersonal debates into relatable, insightful commentary that helps readers better understand human interaction.

Outside of her editorial work, Liberty embraces a holistic, "semi-crunchy" lifestyle as a dedicated homeschooling mother. When she isn’t analyzing the latest trending relationship dilemma, she spends her time meticulously researching and planning her family’s next global travel adventure.

Connect with Liberty on Threads.