May 26, 2026 at 5:20 am

Commuter Buys Coffee for a Homeless Woman Who Ordered Every Single Flavor—Then Watches Her Instant Regret at the Subway

by Heide Lazaro

Woman preparing coffee using a machine

Pexels/Reddit

Kind gestures can sometimes lead to unexpected outcomes.

In this story, a woman regularly offered to buy food or drinks for homeless people during her commute to school.

When a homeless woman asked for a coffee with every flavor available, she agreed after confirming her decision.

Then, as soon as she placed the order and headed to the station, things quickly took a turn.

Read the full story below to find out more.

Want all the flavors? Ok then

My name is Sarah. This is a short malicious compliance story.

When I go to school, I take a bus to the CTA. It is the Chicago subway.

I use it to get to school.

When I see anyone homeless, I offer to get them Dunkin at the station.

This woman saw a homeless woman and offered to buy her something she wanted.

There was this homeless woman.

She was not exactly all there, but she was not aggressive.

So I offered to get her something. She wanted a coffee.

So we went inside.

The homeless woman asked for a coffee with every flavor in it.

I had her order. She said a coffee with every flavor.

I looked at her. I asked if she was sure.

The clerk did the same.

She confirmed.

She bought it for her, only for her to complain later.

So I paid for it plus my own food.

Then, as I was waiting on the CTA, I heard her complaining.

She was warning others to never add all the flavors to one coffee.

Lol. That’s funny! I couldn’t imagine what that would taste like.

It would have been better if she had just chosen one flavor, rather than getting everything.

Well, at least that’s a lesson learned for her.

If you enjoyed this story, check out this post about a thrift store worker who is absolutely exhausted by having to thwart theft attempts until after closing.

Let’s read the responses of other people to this story.

This user shares some interesting info about slushy.

Screenshot 2026 05 25 at 12.05.32 PM Commuter Buys Coffee for a Homeless Woman Who Ordered Every Single Flavor—Then Watches Her Instant Regret at the Subway

This one gives their personal thoughts.

Screenshot 2026 05 25 at 12.06.18 PM Commuter Buys Coffee for a Homeless Woman Who Ordered Every Single Flavor—Then Watches Her Instant Regret at the Subway

Have you heard about the “don’t care” flavor?

Screenshot 2026 05 25 at 12.06.35 PM Commuter Buys Coffee for a Homeless Woman Who Ordered Every Single Flavor—Then Watches Her Instant Regret at the Subway

Here’s a valid point from this person.

Screenshot 2026 05 25 at 12.06.58 PM Commuter Buys Coffee for a Homeless Woman Who Ordered Every Single Flavor—Then Watches Her Instant Regret at the Subway

Finally, short and sweet.

Screenshot 2026 05 25 at 12.07.20 PM Commuter Buys Coffee for a Homeless Woman Who Ordered Every Single Flavor—Then Watches Her Instant Regret at the Subway

Just because someone had offered “anything you like” doesn’t mean you should get everything you want.

Heide Lazaro is a veteran human-interest writer and digital culture expert with over a decade of experience in editorial strategy. Specializing in lifestyle, social dynamics, and the internet's most compelling stories, Heide has authored and published more than 10 books online. Beyond her daily reporting, she is a dedicated motivational speaker who helps audiences connect through the power of storytelling. When she isn't sifting through the web's wildest real-life drama, Heide is an avid runner, painter, and novel-enthusiast fueled by a truly excellent cup of coffee.