June 26, 2025 at 10:15 am

Her Imprisoned Sister Is Demanding Money So She Can Buy Things In Jail, But She Doesn’t Want To Help Her Out

by Matthew Gilligan

woman wearing a red shirt

Shutterstock/Reddit

Folks, this is a tough situation

Imagine having a family member in prison and not wanting to help them out…

Yeah, tough, right…?

That’s what’s going on here and this woman turned to the fine folks of Reddit to ask them if they think she’s being too harsh toward her sister.

Read on and see what you think!

AITA for not helping my sister financially?

“I have two sisters, I’m (40f), the oldest, then 36f and 32f. Our mother went to prison when I was 11 for drugs.

My dad got custody of me and 36f sister, and 32f sister went to live with her dad’s family. So our mom did 7 years of a 10 year bid, came home and established a relationship with youngest sister. Middle sister moved out to our mom as soon as she turned 18.

It’s a complicated dynamic…

I have more of a friendship than a mother/daughter relationship with our mom. She did time, we all suffered in one way or another but successfully made it to adulthood. I’ve raised two children, both grown and doing good. 32 y/o sister doesn’t have kids. 36 y/o sister has one child, age 12.

Now for the bull ****.

36 y/o sister was in the military and doing great, a few years from her 20. Then got wrapped up with a jar head who “knew better and how to work the system ” and she got herself medically discharged.

Things got ugly.

They break up and she goes off the rails. Our mom and stepdad are raising her son. 36 y/o sister landed herself in jail for the next 5 years. States away from all of us so visitation isn’t an option.

My mom lost her job of almost 20 years a few months ago. So, financially she is only paying for my sister to be able to call her son. I accept her phone call once a week if I’m not doing anything or not sleeping.

She likes to call around 8 am on Sunday and I work 50-60 hours a week in a very physical job. I like to sleep in on the weekends so I don’t always answer.

Her mom wants her to be more involved.

Our mom had told me and 32 y/o sister that we need to answer our phones and put money on her books because it’s so lonely in there and she knows what it’s like, and she needs this and that, blah, blah, blah.

Last week 36 y/o sister had the audacity to send me an order form with everything she wanted HIGHLIGHTED on the order form! I saw red and was mad. 32 y/o sister and I are of the mind that we didn’t put her in there, she did and it’s not our responsibility to take care of her WANTS.

Oh, hell no!

If she needs something, soap, shampoo, okay. But the grocery list of snacks she sent me ****** me off every time I think about it.

Now our mom isn’t talking to us because “we don’t know what it’s like and her mom could only send her $25 a month because her brothers (2) were also in prison at the same time and she has PTSD whenever the calls come in and she can’t even talk to our sister.”

AITA for refusing to pay for my sister’s junk food in prison and occasionally missing her calls? You know, because unlike her I have a life that doesn’t revolve around prison schedules.”

Reddit users shared their thoughts.

This person said she’s NTA.

Screenshot 2025 06 04 at 5.12.44 PM Her Imprisoned Sister Is Demanding Money So She Can Buy Things In Jail, But She Doesnt Want To Help Her Out

Another individual spoke up.

Screenshot 2025 06 04 at 5.12.57 PM Her Imprisoned Sister Is Demanding Money So She Can Buy Things In Jail, But She Doesnt Want To Help Her Out

This Reddit user shared their thoughts.

Screenshot 2025 06 04 at 5.13.09 PM Her Imprisoned Sister Is Demanding Money So She Can Buy Things In Jail, But She Doesnt Want To Help Her Out

This individual chimed in.

Screenshot 2025 06 04 at 5.13.43 PM Her Imprisoned Sister Is Demanding Money So She Can Buy Things In Jail, But She Doesnt Want To Help Her Out

And this person didn’t hold back.

Screenshot 2025 06 04 at 5.13.52 PM Her Imprisoned Sister Is Demanding Money So She Can Buy Things In Jail, But She Doesnt Want To Help Her Out

This is a tough situation, all the way around…

If you thought that was an interesting story, check out what happened when a family gave their in-laws a free place to stay in exchange for babysitting, but things changed when they don’t hold up their end of the bargain.