Have you ever lent money to friends or family?

Eh. My mum considers my money to be her money because, as she likes to put it, I "owe her" for raising me.

She never bothers to ask me either, she just orders stuff online using my name.

No, because I never lend money. If someone I know needs it and I have the ability and desire to give it, then it's a gift, not a loan.

If they decide to return it at some point, that's their decision. But I don't put that expectation on them, because I've seen that ruin too many relationships.

I did before, and they either didn’t pay it back when I asked them to/at all, or I just told them they didn’t need it. Sunk costs either way.

Only to my daughter but she paid me back, certainly no one else.

under $100 I will consider it a "gift" i.e. it's a loan but I don't expect it repaid

over $100 and I will get you to sign a contract

yes but its drinks and stuff and I payed for my friends stuffed animal bc she couldn't pay for it

I have given money to friends and family, always consider it as gifts and don't expect it to be returned.

If they do return, then I consider it as a gift to me.

That way, I am spared any disappointment, they any embarrassment and both are sparred breakdown of relationships.

Also on one occasion, I was left short handed, so I requested for help - but not from the person who I had gifted money at that point.

Well I did and regretted about it

Yes.
Just because I don't have children, debt, and loans, they think I'm the best option if they want to borrow money...

Yeah. I lent some to my friend. It doesn't really bother me because as long as I know I have ennough money to take care of myself I do like to help out my friends.