OP, I'm so sorry.

I think you have to figure out what feels right to you, and what feels fair in terms of your family (and especially your husband) and make your decision based on that.

The obvious answer is that no - you don't give someone with the behaviors you describe more money. But things aren't so black and white with family. So what can you live with?

I don't know exactly what I'd do in your shoes, but I've been in a similar place with a sibling and I did eventually have to totally cut him off. The last time I helped him I gave him a gift (not a loan) and said he didn't have to repay me but it was the very last time I would be giving him money. Ever.

Maybe you could give your dad some amount of money in that way, and tell him that this is the last time and if he chooses to end your relationship over it that is his decision.

I'm really sorry.

Anonymous wrote:If he repaid in a timely manner I don't see any problem in loaning it again. What he does with the money is his problem, as long as he pays you back again in a timely manner.

You must be OP's crazy ass daddy!!!!
Do
Not
Lend
Money
He will bleed you dry!

OP, I was you, only chid, family of my own.
Parent who was a gambler. Short answer to loaning money is HELLLLLL NO!
I paid a few utility bills, bought groceries (that were not eaten) and paid for replacement dentures. I hit my limit.
I will not co- sign on dysfunction, it makes it worse. You cannot make someone be someone they are not, you just can't . Loving someone means not participating in your lived ones illness. Set clear boundaries, be willing to help them get in a progr, take to doc appointments. Helping is NOT paying off gambling debts. My parent ended up dying from complications of a chronic illness. This person did not take their medicine, they spent the money gambling. It was sad existence and I feel sadder about that than for having lost them to death. They were just never happy.

1. The threat makes it a no go
2. You need to tell your mom. Her long term financial well being is at stake here.

If he repaid in a timely manner I don't see any problem in loaning it again. What he does with the money is his problem, as long as he pays you back again in a timely manner.

I dunno, he repaid last time, so I would be tempted to loan again.

Nope. If you loan it, you are enabling. You said last time was a one time thing. Time for him to get help.

Just say you can't afford it. No way no how.

No, I would not. I dont believe being a close relative is a free ticket to be a dick.

OP, don't do it. Just let him know you don't have that kind of money right now. Blame it on something else if you find it hard to turn down...car repairs, new water heater, etc...

Anonymous wrote:Not a chance. I would happily purchase groceries, help out with utility bills if necessary, but no way I would give money for a gambling debt. His wife likely has him on a tight financial leash and others giving him money enables him and undermines her efforts for him not to gamble. If he ends his relationship with you, so be it. If he is willing to do this, the relationship is not worth having.

I'm sorry your dad is like this, OP.

I totally agree. It's blackmail of the worst kind. So sorry

Not a chance. I would happily purchase groceries, help out with utility bills if necessary, but no way I would give money for a gambling debt. His wife likely has him on a tight financial leash and others giving him money enables him and undermines her efforts for him not to gamble. If he ends his relationship with you, so be it. If he is willing to do this, the relationship is not worth having.

I'm sorry your dad is like this, OP.

If a parent who had a gambling debt asked you their only child (having 2 kids and living comfortably but no real extra income) for money would you give? This is the second request having lent $5k first time that was repaid in a timely manner. It was made clear it was a one time favor though. He's borrowed from everyone else and really doesn't have any viable sources (although there are several other distant relatives that could help but he won't ask out of pride). It's not a life/death situation, it's also not something that is clear on what this money is needed for could be a past or current debt nor to whom. But it is true he probably feels compelled to ask me as a last resort. There is a question of whether his wife is aware of the situation and/or whether he truly needs to borrow (in reality) or just wants to borrow so as to not spend his own. He's not a great person and the history of the relationship has been tumultuous. Nevertheless there's no other immediate family - mom or siblings - by not lending the money the relationship will end from his perspective as he "will remember it." So - is a relationship worth saving with someone like this and 2. If so, how many times do you lend the money - what happens next time if he asks? And 3. Even though I like to be repaid if not we will be ok - is it really helping him?

He's still my father - is there a line drawn with family?

Husband supportive and the amount asked for is similar to first loan amount. Wwyd?