Pay Dirt is Slate’s money advice column. Have a question? Send it to Kristin and Ilyce here. (It’s anonymous!)

Dear Pay Dirt,

I am a 77-year-old man with two adult children. My wife, their mother, died three years ago. Last year, I met a woman who is two years my junior, and we had a connection. Our relationship has been a small miracle for an old man who thought that part of his life was behind him.

The “problem” I’m writing about is about our difference in economic circumstances. I’ve had many lucky breaks in my life, and I have the wealth to show for it. My girlfriend has not enjoyed the same economic prosperity in her life. She is a single mom to one daughter and a true American “pull yourself up by your bootstraps” story. She became the second person ever in her family to graduate from college at age 45 (her daughter was the first). She is a remarkable woman. She retired from teaching at age 65 and lives on a very fixed income. When we met, she was on a once-in-a-lifetime trip for her, her very first cruise, with her best friend. It was my ninth cruise that year.

Anyway, we live in different cities. I own a huge house on the water in my city. She lives in a small rental, so I have been flying her out here or we meet somewhere between us. I always pay, of course, and when we are together we stay in hotels of my standard, which she has never experienced before. It does feel nice to be able to give her these experiences, but I’m also struck that she goes home to live a very frugal lifestyle while I go home to my own lifestyle. I have visited her city once, and we stayed at her apartment one night before going on a roadtrip. It was very small and not very comfortable, though she had of course done what she could with it.

She is already someone who is very important to me, and I keep thinking about how I could make her life easier with some of my money. For example, giving her the downpayment for her first home or, if she isn’t interested in buying, giving her money so she could move into a nicer apartment. I also think about leaving her something if I die first, but I think I’m more interested in giving her this money now. But I don’t know what’s “appropriate” or who to talk to about it. And I do have some concerns.

My main reservation is my kids. My kids know that they’ll split what’s left of the estate when I die. I’ve never been forthcoming with them about exact amounts. But I do imagine that, if they cared to, they’d be able to see whatever gifts I give her now, if they wanted to do some forensic accounting. I don’t really think they’d object, but I haven’t talked to them about it. They know that I am with my girlfriend and say they are happy for me but they also, it’s clear, are not interested in meeting her. So that is one thing that gives me pause.

My other fear, I’m sorry to admit, is that if I did give my girlfriend a large gift, she would no longer be interested in me. Or that if I made it an “allowance” it would really underlie our difference in status and change our dynamic. There’s nothing that has made me feel that she’s only with me for the money, but it’s certainly something she enjoys and something I feel proud to be able to offer her. Perhaps part of that for her is the idea that there might be something more for her, financially, one day. (Though I was clear from our first meeting that I will never remarry.) I would be very sad if giving her a large gift now ruined our relationship, which I have come to cherish.

Can you help me think this through?

—Late-in-Life Boyfriend

Dear Late-in-Life Boyfriend,

Stop. Your girlfriend hasn’t asked you for anything. She hasn’t complained about her apartment or how hard her life is. She hasn’t hinted that she needs rescuing. So why are you so eager to swoop in with your checkbook?

You spent one uncomfortable night in her small apartment and now you can’t stop thinking about buying her a house. That tells me this is about your discomfort, not hers. You feel awkward about the disparity between your financial states. But, she’s going home to a life she built herself—a life she’s apparently proud of, given that “pull yourself up by your bootstraps” framing.

Think about it this way: Maybe she likes her independence. Maybe she doesn’t want to be someone’s charity case. Maybe the relationship works precisely because it isn’t tangled up in financial obligation. You don’t know, because you haven’t asked.

Before you do anything, examine your own motives. Are you trying to lock her in with money because you’re insecure about what else you bring to the table? Are you feeling guilty about the inequality? Those are your issues to work through, not problems for her to solve.

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The best thing you can do is talk to her. Not “I want to buy you a house”—that’s overwhelming and presumptuous and frankly a little weird. Try: “I really enjoy our time together. Is there anything I could do to make your life easier or more comfortable?” Then listen to her response. If she says she’s happy with what she has, believe her. She might be happy just spending time with you and having you treat her to things she couldn’t otherwise afford. Right size gifts might include continuing to cover her travel costs, buying her a new phone, a lovely piece of jewelry, or a gift card to her favorite store. Not a car. Not a house.

Once you feel more settled with your friend, talk to your kids. Why won’t they meet someone who’s been important to you for a year? Are they still grieving their mother? Do they see any woman as a threat to their inheritance? You don’t need their approval to spend your money any way you wish, but you should understand more about their reticence before doling out the bucks. They might be concerned it’s too much too soon and they don’t realize how significant a part of your life she is, even if you’ve decided not to remarry, a fact they might find comforting.

—Ilyce

Classic Prudie

I’m in a pickle, or rather my son is. He is 17, is about to graduate high school, and likes to smoke pot, which is illegal in my state. He has been through a teen-intervention course for having pot and paraphernalia in his vehicle (teen court, tour of the jail, the works), and we thought that would scare him, but once he met his community service requirements, he started smoking again. This past December, between his work and holiday money, he spent about $500 on pot. He wants to move out and live on his own when he is 18—he says his goals are to just “work and smoke pot.”

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