AITA for giving a sitter a Xmas cash present?

A Redditor shares their story about giving a cash Christmas gift to their brother’s neighbor, Teddy, who often babysits the brother’s three children. The sitter, who went above and beyond to care for the kids while the brother was hospitalized, received heartfelt cards from the children and a financial token of appreciation from the Redditor.

However, the brother felt the gesture was excessive, claiming it made him look incompetent and could pressure Teddy into spending more time with the kids. Now, the Redditor wonders if they overstepped by giving the gift without consulting their brother. Read the full story below to weigh in on this family dispute.

‘ AITA for giving a sitter a Xmas cash present?’

My brother, Chris, is a single dad with a 15yo, 10yo and 7yo sons. He’s been dealing with multiple health issues. Luckily for him, I do have and make a nice amount of money to help them stay afloat and they don’t realize that they are poor.

Chris lives next door to a family and they have a son who is in his 20s named Teddy. He occasionally watches the younger two when Chris has to work or is not feeling well. A couple of months ago, Chris had to be admitted to the hospital for a few days and the neighbor cut his vacation early to watch the boys.

I was out of town but I was impressed that the boys didn’t miss any sport practices, the house was clean, laundry done and Teddy actually got the younger one bathed every night.

I do watch the younger two and it’s likely all three will eventually move in with me nect year and my brother might have to be put in a specialized care. On Tuesday I went to pick up the boys to do Xmas shopping and the 10yo asked if he could see Teddy.

I asked why and he said he had to give him something but wouldn’t say what. I found out my nephew made Teddy a Xmas card and saying he was sorry that he couldn’t buy Teddy something because he was broke.

I pretended that I didn’t know about the card and told my nephews that Teddy does a lot and we should give him a gift. The younger two made cards and the oldest bought one. I put cash in the envelopes and the boys put the cards in their mailbox.

My brother called me today and asked if I gave Teddy money. I said yes. He said that wasn’t my place and he was going to give Teddy like $50. My brother said the amount was excessive and made him look incompetent.

He said at the very least I should had asked him if that was cool with tipping his babysitter and all of a sudden Teddy feels obligated to spend time with them. I said I didn’t do anything wrong. This kid is richer and your son isn’t embarrassed about being poor and now you got a free sitter.

Here’s the input from the Reddit crowd:

Humble_Guidance_6942 −  NTA. You are a kind and generous soul. Your brother is trying to gain some semblance of control. Try to be a little patient with him. It is not easy to get sick and go from provider to burden. Thanks for stepping up for your family. I hope you have a wonderful Christmas with your family. I pray that your brother recovers.

Aware_Welcome_8866 −  NTA. Cash is the gift of choice for service providers. Also, tucking it in cards made by the boys doesn’t indicate who gave the gift. Is Teddy really spending more time with the boys, or is that what your brother fears will happen? That seems simple enough to solve. Just tell Teddy it was a gift, no strings attached, and you will continue to pay for his services as usual.

insignificantlittle −  NAH. You did a great thing, your brother is feeling embarrassed.

mostly_lurking1040 −  What you did was nice, but your brothers comments make sense. You could just be an adult and tell him you’re sorry you didn’t think of that. The gifts were really from “the family” and included him of course. Tell him in the future you’ll be coordinating anything like that with him.

RoyallyOakie −  NTA…Your brother should be gifting you two free words: thank you. Putting the money in cards made by the boys makes the gesture sweetly personal. Well done.

Desperate-Film599 −  I’m actually going with NAH. Same reasons others have stated. Your brother is going through a lot. He’s probably just frustrated and feeling out of control. His lashing out at you wasn’t nice, but good on you for trying to understand and let it roll.

Your brother is incredibly lucky to have someone he can trust with his kids. Especially on a moment’s notice. A lot of 20 year olds wouldn’t step up like that. And to do such a great job.The fact that your nephew made Teddy a card? Says a lot about how much he cares about Teddy. And wanted to give him a gift!

You facilitated that. You made it a fun project. I have no doubt those boys were beaming with happiness when they gave Teddy those cards. Thank you for giving them that. They will remember it.

I’m a service provider. I freaking LOVE Christmas bonus cash. Maybe you were a little extra. But a single parent with a reliable sitter living right next door and willing to drop everything in the blink of an eye? Absolutely f**king PRICELESS. Worth every penny you gave that kid.

Tell your brother you’re sorry. Didn’t mean to step on his toes. You got caught up in the excitement of the moment with the boys. And you just wanted to show your appreciation to Teddy for being so wonderful. I’m guessing all of those things are true. It sounds like his pride was hurt.

It’s gotta be rough losing his health and relying on others. Of course you weren’t wrong and didn’t deserve being chewed out. But this is one of those magical unicorn times when you actually should just be the bigger person. You can be happy… or you can be right.

This sounds like one of those times when it isn’t the hill you should die on. Sounds like he’s got worse things heading his way. Give him grace. He’s lucky to have you too. Thank you for being so thoughtful. 

Usrname52 −  YTA in terms of you being wrong. I don’t really want to say you’re an AH, but I definitely think that doing it through the kids’ cards was really bad form. The obvious assumption would have been that it was Brother, and that Teddy would call and thank him.

Which puts him in an incredibly awkward position of being blind-sided and have to say “I didn’t give it,” and setting a precedent that your brother can’t keep up with. You could have just sent a card saying “Teddy, Thank you so much for being an amazing support for my nephews in this tough time. Happy Holidays, From, OP”.

greenpepperprincess −  He said at the very least I should had asked him if that was cool with tipping his babysitter. Your brother is right. Simply asking him would have made all the difference. Soft YTA.

appleblossom1962 −  NTA. It wasn’t a tip. It was a Christmas gift.

swillshop −  I’m going to tell you NAH. You did something nice, and truthfully, your brother shouldn’t be upset with you. But please have compassion for him. He is struggling with a lot, and there’s so many things he can’t do/needs help with. He is not as clear-eyed as he might normally be.

You didn’t do anything wrong at all, but just let this dust-up fade away. If you have it in your heart, you can tell your brother, “I didn’t meant to step into your place; I was just reacting to the moment and trying to be helpful.” That’s not a lie; nor does it indicate that there’s anyone to blame.

If you don’t feel like saying that, I still think you are fine – you’ve been doing a LOT for your brother. You have your own stresses, and you’re human, too. Sending good wishes for all of you.

Was the Redditor wrong for giving a generous gift without consulting their brother, or was the gesture justified given Teddy’s contributions to the family? How would you balance showing appreciation for someone’s help while respecting family boundaries?
Share your thoughts in the comments below!