If you’re going to give a family member a large financial gift, you can’t dictate what they do with that money. You can advise them all you want not to blow five figures on online sports gambling, but if they’re determined to do so, they will do it. If you’re loaning money to a close family member or friend, that totally changes the dynamic of the relationship. One of you now is financially indebted to the other, so you cannot be equals. Gifting someone money can be a great way to help out without totally changing your relationship to one where one person has power over the other. But if you’re going to gift someone money, you have to be okay with that money going to something you deem foolish. There’s a reason people don’t give large sums of money to extremely irresponsible family members. They don’t want to see it go to waste.