I’m a lottery millionaire. I can’t believe what my family is “forbidding” me from spending it on.

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Dear Care and Feeding,

My neighbor, “Treena,” came out to me as a lesbian when she was 16 and asked me not to say anything to her parents, as they are very conservative Catholics. Last summer, the day after Treena graduated from high school, her parents found a card from Treena’s girlfriend and confronted their daughter about her orientation. When Treena told them she was a lesbian, they kicked her out and she ended up on my doorstep, sobbing, with a hastily packed suitcase in hand. To add insult to injury, her parents also refused to pay her tuition at the college she would be attending in the fall. I let her crash with me, thinking her parents would come to their senses. They have not. My attempt at asking them if they would be willing to reconcile with her was met with a terse “you took the little (anti-LGBTQ slur) in; she’s your problem now.”

Twenty-five years ago, I won a significant amount of money in my state’s lottery, and thanks to savvy investments I am set for life—several lifetimes, in fact. I am not married and don’t have kids of my own and have decided to pay Treena’s way through college. Treena left for school in August, and I am happy to say she is thriving away from her repressive parents.

A few weeks ago, I was having lunch with my sister, “Madison,” and told her about what happened to Treena. Madison was all sympathy—until I told her of my decision to pay for Treena’s education. Then she upbraided me for “paying out so much money for someone who isn’t family.” That’s when things started to go off the rails.

I was extremely generous with my entire family when I won the lottery money. I paid for my niece’s wedding and bought her and her husband a house. I fully funded Madison’s son’s college tuition and am currently paying for her daughter’s graduate program. I covered Madison’s legal bills when she divorced her ne’er-do-well husband, and bought her a new condo so she could have a fresh start. I am also paying for our parents to live in an expensive retirement community. In spite of all this, paying for Treena’s education isn’t going to put a dent in my finances; our entire family will still be extremely well taken care of.

When I pointed all this out to Madison—along with the fact that I have known Treena since she was 3 years old—my sister got huffy, so I left. She has been giving me the cold shoulder since then, and, worse, has told everyone that Treena is using me for money. There has been no end to correcting the record with numerous friends and relatives. About half have been understanding and are disgusted with Madison, but the rest believe her and have been haranguing me about my decision to help Treena.

I am furious over the rift Madison has caused in the family and am half-tempted to stop paying for my niece’s graduate program, but I don’t feel right punishing her for her mother’s deplorable behavior. All I want is for things to go back to the way they were, especially with the holidays just around the corner. I usually host a big gathering that we all look forward to, but since Madison upended everything, I know I’m going to be spending the entire time being hounded by half my relatives about this. The trouble is that it will cause even more friction in the family if I exclude those who think they have a right to tell me what to do with my money. What’s the solution here?

—My Bottom Line, My Business

Dear My Bottom Line,

I get why it feels terrible to be subjected to your relatives’ interrogations and condemnations just because you’ve chosen to be generous with a young family friend—particularly when many of those relatives have benefited from your generosity over the years. I’m glad you were there for Treena when she needed you, and of course it’s very kind of you to finance her education. It’s not as if you’ve denied your relatives the same support, so they truly have no cause to be upset.

The immediate decision you’re facing, about whether or not to host your annual holiday party, really depends on you and how much you actually want to see and spend time with Madison and other trouble-making relatives right now. If you think it would make for an unpleasant experience with half the guests harassing you over your kindness to Treena (which again, is frankly bizarre on their parts), maybe you should just do what feels best for you and forgo the big party this year. You might feel sad about that—which is ok; you have a right to—and others may be peeved if they aren’t invited to the festivities. But you know, if people wanted to be invited to your place for the holidays, they could have behaved better. Carefully expressing concern is one thing; being angry with you for helping Treena is another. You don’t owe anyone a huge party, ever, and you definitely don’t when they are currently committed to judging how you use your own money. Spend time with the people you want to spend time with, and protect your peace during the holidays.

As for all the days after, it could go a few different ways over the long term. You should tell Madison and anyone echoing her selfish arguments that this topic is off-limits, and be ready to end the conversation if they don’t listen. Make it clear that their petty pressure campaign is pointless, because your mind is made up about helping Treena. Left on their own to stew, Madison and your other difficult relatives might exhaust themselves and give up this particular fight, particularly once they realize it’s futile. I strongly suspect that they won’t want to risk permanently alienating you or losing their own access to your money.

I don’t wish to invent motives or hurt your feelings, but I think it’s worth considering why Madison and others are behaving this way. Because I don’t think the real issue is that they feel entitled to tell you what to do with your money; I think the issue is that they clearly feel entitled to the money itself—so much so that they can’t even bear to see some go to Treena, a young woman who has essentially lost her family due to no fault of her own. You helping her doesn’t take anything away from your relatives, who will still want for nothing if you continue to be generous with them. While you don’t have to cut your niece or anyone off at this moment, I do think it’s ok to let your family know that if this is the attitude they’re going to have, you will need to seriously consider how much assistance you offer them in the future.

—Nicole

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