October 26, 2026 at 5:15 pm

Woman’s Friend Gives Her Money For A Medical Procedure, But When They Have A Falling Out, She’s Not Sure What To Do With The Money

by Jayne Elliott

confused woman holding cash

Shutterstock

What would you do if you were friends with benefits with someone who tried to have the same sort of relationship with your younger sister? Would you be okay with that or end the friendship?

In this story, one woman is in that situation, and she ends the friendship, but that’s not even the real problem. The problem is that he gave her money when they were still friends, and now she’s not sure what to do with the money.

Keep reading for all the details.

WIBTA if I don’t give him his money back after he hurt my feelings?

I (F28) had this friend (M36) for 10 years. There were never any romantic feelings between us, but we did hook up once or twice some years ago.

We didn’t see each other that often, but I considered him a good friend.

Anyways, a few weeks ago, when I was hanging out with him, the topic came up that I had postponed a (minor) medical procedure because I didn’t have enough money for it.

This is very generous.

He just reached into his pocket and gave me some money, which is worth about $570.

I tried to decline it, but he insisted.

So I thought, why not? He has enough money, and I was very touched by the gesture.

This guy sounds like a player.

A few days later, we went to a party together and hooked up afterwards (that’s unrelated to the money transfer). “Hooked up” means up to third base.

I was in kind of a vulnerable state, so I accidentally caught some feelings for him. Which was stupid, because we just don’t match as “lovers”. But whatcha gonna do?

I also hang out with my much younger sister (F21) sometimes, so it happened that we all hung out together one day. Long story short, he hooked up with my sister like four days after he hooked up with me.

I am still very much confused about how he could think this was okay behavior.

She knows her sister isn’t completely innocent in this.

I was also very mad at my sister, but I forgave her because she’s young and stupid.

But he is like 36 years old?

I talked to him about it, and he was all like, “Ohhh, did it hurt you? I didn’t mean to… The timing was not ideal, admittedly.”

I then asked him to stop doing that with my sister.

She’s over him.

And he was like, “I need to think about it.”

Then (3 days later…) I was like, “Save it. I don’t wanna be your friend anymore. I think what you’re doing is wrong because of the age gap and because you’re inserting yourself between sisters.”

He then proceeded to hook up with my sister, and I stopped talking to him.

She still has his money.

So my question now is: what do I do with the $570? I don’t want it because I don’t need anything from that jerk. I haven’t spent it for that reason either. WIBTA if I don’t give it back?

Bonus question: What can I do with it? I don’t want to spend it on myself because I have principles.

I could also just give it back through a mutual friend. But I thought maybe there is something funnier to do with it, or I could give it to charity.

He gave her the money for a medical procedure she couldn’t afford. She should use it for that, the intended purpose.

Let’s see if Reddit agrees.

This person thinks she has two options.

2026 10 23 at 9.32.53 AM Womans Friend Gives Her Money For A Medical Procedure, But When They Have A Falling Out, Shes Not Sure What To Do With The Money

Another person tells her not to steal.

2026 10 23 at 9.33.02 AM Womans Friend Gives Her Money For A Medical Procedure, But When They Have A Falling Out, Shes Not Sure What To Do With The Money

This person thinks they all sound awful.

2026 10 23 at 9.33.18 AM Womans Friend Gives Her Money For A Medical Procedure, But When They Have A Falling Out, Shes Not Sure What To Do With The Money

If you enjoyed this story, check out this post about a woman whose family wants her to spend way too much time redoing paintings to make them match.

I have the same question.

2026 10 23 at 9.33.39 AM Womans Friend Gives Her Money For A Medical Procedure, But When They Have A Falling Out, Shes Not Sure What To Do With The Money

I wonder what happened that she doesn’t want to use the money for the medical procedure anymore. She should just use it for that unless something really changed where she doesn’t need it anymore. In that case, she can have a third party give the money back.

She’s better off without him.

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Jayne Elliott | Contributing Writer, Life & Drama

Jayne Elliott is a contributing writer and editor for TwistedSifter specializing in human interest stories, internet culture, and family dynamics. With over 12 years of editorial experience in digital publishing, Jayne excels at analyzing complex online communities and transforming viral social debates into thoughtful, highly engaging narratives.

Rather than simply aggregating internet drama, Jayne brings a sharp, empathetic editorial eye to everyday dilemmas. She has a unique talent for unpacking the nuances of pop culture and online conflicts, providing readers with relatable, well-researched commentary.

Based in California, Jayne spends her free time outside the newsroom exploring theme parks with her family or beach-combing along the coast.

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