My Problem Is Solved.) Disregard.

I understand wanting the money but if it's like $5, she just may not think it's a huge deal and therefore forgets. If they are well off, it wouldn't be foremost in her mind bc she wouldn't think $5 would be a concern. But you gave her an out. She said she wanted the tshirt. I don't think you should feel like you pushed her into it. So no problem being gently persistent. I feel like there's always someone is slow paying or doesn't. It's always a risk when you put money up front. I always try really hard to make sure I repay but who knows - I may have spaced somewhere along the way and I'm very money conscious too and really try to repay. Reminds me I think the family we carpooled to soccer with never repaid me for a team item I paid for. Other familes I barely knew paid me. They have the money for it bc it wasn't a lot ($5?) but I also know they're just a disorganized family... Sucks to have to keep asking but do so nicely and don't be too mad at her. If it's over $20, then I'd start to get mad and we're not even pinching pennies. That's just an absolute amount of money that someone should repay... Then I'd start getting less polite about it.

No good deed goes unpunished. I can totally relate. We can speculate on her financial situation all we want, but it doesn't change the fact that she did say she would pay you back. It's irresponsible of her not to pay you back. If she can't afford it, she should've told you up front. I'd just text her one more time and let it go.
So sorry you're going through this. If people owe me money, you bet I want to be paid back. You don't have to miser or scrooge to want your money back.

No, I don't think you are a Scrooge. I wonder if she has just forgotten, or if she really doesn't have the money to give you or if she sent it with Johnny and it never made it to you. I think I would call her and tell her you haven't gotten the money yet and that you would appreciate it if she could settle up with you. See what her response is. If she is in dire financial straits, I would let it go and avoid buying things for her son that you expect to get reimbursed for. If you like this boy (your son's friend) and you want to be kind to him, i would buy the shirt out of my own pocket. I'm guessing this doesn't happen very often.

Not a scrooge, but forgetting does happen. It doesn't sound terribly responsible, but sometimes I have to do something right in the exact moment that it's on my mind or I will completely lose that thought. That might happen multiple times before I actually get it done. Send her another text that simply reads, "Reminder". See what happens after that.

You did this without first talking to the other mom. What if she is in a similar situation as yourself or worse to where she cannot afford to pay you? She agreed to do so perhaps more out obligation than anything else. I'm not saying she isn't beyond grateful for you doing what you did for her son. If you knew that making that extra purchase would put you in a pinch, be it monetarily or emotionally, you should've passed. I realize that yes then the other child may have felt left out but sometimes you cannot always help others. However, if I were you I would just chalk it up to a lesson and if/when this happens again in life don't put yourself out unless you can do so without issue.

Thank you for including the other child and whether you are paid back or not look at what good it did for that child. That is what should be the main focus at this point as to not bring extra stress upon yourself. Smile at the good deed you did and move on.

Here is the thing. You bought it. She didn't ask you to. You chose to. And it was nice of you. Let it go.

You don't know what her tax bracket is. unless you do her taxes. You might know where she lives. But again you don't know her situation. We lived in an affluent neighborhood. My kids went to private schools. We drove nice cars. I was going through breast cancer treatments and my husband was hurt at work. he was off for 7 months. we still lived in the same house, same schools etc as we had paid tuition ahead. But we lost our house and until it happened no one knew about it. Because we were going paycheck to paycheck before I got sick and hubby got hurt. my son went to a birthday party where the parents paid for the bowling. but each kid was required to pay for their own shoes. he didn't have the money and he wouldn't ask us for it. the parent was pissed at him because he came without the money for shoes. when she said well can't you ask your mom he said nope and explained why. she was shocked. I was embarrassed. You don't really know whats going on. But bottom line you chose to purchase this shirt for the kid. Let it go and use it as a lesson. Don't purchase stuff for others unless you get the money first. The bad feelings that you hounding her for it may come back to bite you later.