Dear Penny: Should I Give Money to My Jailed Nephew’s Girlfriend Again?

A woman's reflection is shown on a blue and yellow wall. She's holding a toddler.
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Dear Penny,

My nephew is currently in jail and has been most of his adult life. He is 41 years old. During one of his releases, he met a girl in rehab, and they were in love and conceived a baby, who is currently 2 years old. My nephew was sent back to jail when the baby was 6 months old for a parole violation. The mother of his child is not working and does not drive or own a vehicle and lives with her mom.

Initially in December 2021, when they reached out to me for help, I gave them money to help out with the baby. I had never met the baby’s mother. She indicated that my nephew would be released in June of 2022. I gave them over $3,000 during this period. When my nephew got into more trouble in jail, they extended his release date to ???.

I have chosen to refrain from giving more money, and the baby’s mom incessantly continues to beg me for money. I don’t want to assist any longer, as it’s digging into my hard-earned savings. I have realized that doing something nice for them, initially, has now put me in a position where they have grown to resent me. I understand their situation and choices are their responsibilities, and they should take accountability; however, I was helping out for the baby, not my nephew.

— Disheartened Family Member

Dear Disheartened,

Isn’t it ironic how when you help someone, it often spurs resentment instead of gratitude? Still, I get why you feel torn, given that you just want the best for this child. But you’ve made your decision, and I think it’s the right one.

I’m not sure if you’ve met your nephew’s girlfriend since you initially gave her money. Regardless, I don’t think you know her well enough to be confident that any money you’d give would actually go toward the baby.

Dear Penny

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Now you need to stick to your decision. Your nephew and his girlfriend’s feelings on the matter are irrelevant. I’d suggest shutting down any future requests without engaging in a drawn-out conversation.

Next time your nephew’s girlfriend begs you for money, respond with a simple “no,” or “I’m not going to give you money again” or “I’m not in a position to help out.” End of discussion.

Avoid discussing the “why.” As in, don’t explain that further assistance would eat into your hard-earned savings or give any explanation of your own financial situation. Someone who constantly has their hand out will only use that information to argue about why they need your money more than you do. Likewise, don’t lecture your nephew’s girlfriend about accountability or question her life choices. When you say more, you give the impression that something is actually up for debate.

If you’ve made it clear you won’t be helping out again, I don’t think you need to respond to future communications from your nephew’s girlfriend. You could simply ignore her texts or phone calls. You could also put her contact on “Do not disturb” so that she’ll be muted when you don’t want to communicate, or you could block the contact altogether.

Since you’ve given the girlfriend money in the past, you’re a logical place to start when she needs cash. But if you consistently say “no” or you simply don’t respond, my guess is that she’ll eventually move on.

If, for some reason, you want to help your nephew’s son in the future, I’d avoid giving cash directly to the girlfriend. For example, you could buy them groceries if she says she’s out of food instead of giving her money. But again, that’s only if you change your mind. You’re not obligated to offer any assistance.

I think the hard part here is that you’re more or less powerless. Sending another $3,000, or even $10,000, isn’t going to change the fact that this child has been born into a really tough set of circumstances. Nor will it prompt his parents to make different life choices.

Try not to waste any more time worrying that your nephew and his girlfriend resent you. They’re allowed to have their own thoughts and feelings, no matter how illogical they may be. But let this be a hard-won lesson about the high price of helping someone out. Stand firm, and don’t let your nephew or his girlfriend treat you like a human ATM.

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Robin Hartill is a certified financial planner and a senior writer at The Penny Hoarder. Send your tricky money questions to [email protected].