To ask for money

[ForBrickSnake]

My older brother over the years has been crap paying his way or expecting something for nothing.

99% of the time I hear from him when he needs something, hardly visits, never invited round. He lives a 10min walk away.

Now he is plastering his holiday for this year abroad and next year too.

I'm so tempted to invoice him for things ive helped him with, car rental, joint birthday gifts where he didn't pay up. Picking him up when car broke down etc. Why don't people say here you go when they can - paying things back. I'm such a bloody mug.

YANBU but all you can really do is too being a mug. Do you send him birthday or Christmas presents? Stop! And no more shared presents.

You are not being unreasonable to ask for money off him but I doubt it will be repaid.
Personally I'd wait until the next time he asks for money and say I'm glad you've brought it up because I won't feel comfortable ever lending you money again as there's been all these occasions you haven't paid me back (list a few and see what his response is)? Just be ready for the conversation to happen, or better yet pick a time he's rolling in money and telling him you really need to borrow some, when he asks how much then say hmm probably about as much as I lent you for x,y,z etc!!

I would probably be very sarcastic and say must be nice to have holidays when you still owe me x amount but at least I know you won’t be asking me for a loan ever again or going halves for gifts when you obviously have money.

Sounds just like my brother OP. He is now saying he can't attend mum's big birthday party as either date we have proposed clashes either with work or a works do. I told him he can go to work's do anytime his mum isn't going to be 70 again. It's just pure selfishness. Some people just don't care that much about other people. I stopped lending him money years ago.

You resent him for picking him up when his car broke down, really? Surely that's just something siblings do to help each other out and not keep score.

It's in the context of everything else he's done/not done. But you know that.

No the other stuff I get but that just seems like a favour you'd do for a family member or friend.

so you can mention it now, he won't pay you back obviously but next time he asks for a handout - ready the response "I don't lend money anymore, been too many instances of not being paid back"

I had a "friend" who kept asking us for money, £10, £20 here and there, never paid it back then there was an ask for more, this one was quite funny because she also asked my husband for money and hour before in a FB chat, telling him she was waiting to hear back on a loan - whilst messaging me the same ask - i was the loan! obviously not realised we communicated... so the "I don't lend money anymore, been too many instances of not being paid back" was the answer in both the messages.

then it was "can you be a guarantor" that was a definitive no as well. Repeat until they stop asking.

You keep lending, they keep asking. You're the cause of the ongoing problem.

It was your choice you weren't forced into it?