Dear Prudence

Help! My Fiancé Just Won a Bunch of Money Gambling, but He Won’t Share Any With Me.

Read what Prudie had to say in Part 2 of this week’s live chat.

Woman sitting with her head in her hand on top of a graphic of a cruise ship.
Photo illustration by Slate. Photos by Getty Images Plus.

Dear Prudence is online weekly to chat live with readers. Here’s an edited transcript of this week’s chat. (R. Eric Thomas is filling in as Prudie for Jenée Desmond-Harris while she’s on parental leave.)

Q. Not smooth sailing: I am struggling with my feelings about a vacation I just took with my fiancé.

I gave my fiancé a cruise with his favorite musician as a birthday gift. I paid for everything, including a high-end cabin and specialty dining. During the cruise, he spent a lot of time in the casino and won the equivalent to the entire amount I spent, plus about 30 percent more.

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He pocketed all of it. This is typical. He gambles on vacations (not problematically) and often wins, but never does anything for me or us with the money.

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Shortly after we got back from the cruise, an expense came up with the house we co-own. I told him I needed him to cover it because I was tapped out. He was really pissed that I wouldn’t split it as we normally do (40/60 because he makes a lot more than me). He didn’t express a shred of gratitude for the cruise.

Am I right to be concerned that he is all about splitting costs, but not sharing the wealth? Or am I just feeling embarrassed that I overspent and wasn’t prepared to meet our agreed obligation? I also feel bothered that he is so focused on splitting things instead of viewing us as a household. We have only been engaged for eight months but we have lived together for six years. I’m guessing this won’t change after marriage and it feels bad to me—but is that because I make less? Were his actions selfish and a potential red flag, or am I the one being selfish?

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A: It sounds like that cruise struck an iceberg that runs a lot deeper than it appears. Your mind has changed about your financial arrangement. This is fine; it happens over time. But your frustration is coming from the discord between your new perspective on your shared finances and the old rules. You’re not being selfish, but it’s not fair to be resentful if you haven’t talked to your fiancé about your new relationship with money.

It’s time to renegotiate. When you sit down to talk about money, make sure to begin by talking about what money means to you, and how you respond to it emotionally. It’s possible you place emotional value on money in different ways—he’s a gambler who likes debts to be settled fair and square; you saved and sprang for an expensive gift as a token of your love. Both of those expressions are fine and not necessarily mutually exclusive. But you both need to talk about how money will work for you going forward.

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How to Get Advice From Prudie:

• Send questions for publication here. (Questions may be edited.)

• Join the live chat Mondays at noon. Submit your questions and comments here before or during the discussion.

Q. Trying to move on: My girlfriend and I have been together seriously for nine months. I have a 12-year-old and a 9-year-old, and she has a 4-year-old.

My ex and I have a strict custody schedule because of the bad blood between us. Short of fire and blood, we go exactly off the custody orders and switch off at a local coffee shop. My girlfriend had the opposite problem. She and her ex get along too well, in my opinion. They broke up during the pregnancy, but he started to spend the night to help with the baby three nights a week. They still do this because their kid refuses to sleep anywhere but their own bed. The ex had a bedroom for them at his place but will sleep on the trundle bed here instead.

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My girlfriend and her ex don’t have lingering feelings; he has his own girlfriend. But this arrangement is killing our future.

The 4-year-old has fits if Daddy doesn’t spend the night, and will cry until they are sick if they have to spend the night anywhere but home. I had to get up and make awkward small talk with the new girlfriend, who slept on our sofa because it was their date night.

This is weird and getting to be too weird for me. I love my girlfriend. Our kids get along. We are discussing marriage, but it is hard to take it seriously when her ex spends more nights here than I do. They aren’t having sex but are too tangled up together for my comfort. My girlfriend says I am biased and unfair, considering my relationship with my ex.

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A: I know it’s hard to navigate the superclose relationship that your girlfriend has with her ex, but it doesn’t sound like a shared problem. In fact, it seems like they’ve worked out something that fits their lives and the life of their child. Even if he stops coming around as much, he’s always going to be in his kid’s life, so the question you have to ask yourself is “Am able to be a part of this system?” And maybe the answer is no, and that’s OK. But I’d encourage you to find ways to be an asset to the larger unit and to support your girlfriend. If you don’t want to make small talk with the ex’s new girlfriend, you don’t have to. But just as these people have worked through the weirdness in service of something greater, you can too. If you want to.

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Q. I swore an oath: My brother is dying. We have a large family, and he has been estranged from everyone—except me—for decades. Prior to him telling me that he was in a terminal condition, he made me promise not to reveal what he was about to say to anyone. I agreed. Now, I feel terrible, because this will be his last chance to possibly reconcile, or maybe just speak his piece, or maybe just see them once more.

I know the chances of reconciliation are slim. I know my brother doesn’t want it. I know the rest of my family has written him off, forever, and for reasons that many would agree with (he’s never done anything evil; it’s politics and demeanor). I feel bound to keep my word, but at the same time, I don’t want my angry, difficult brother to be mourned by just one, when there’s an equally angry, difficult family that once loved him.

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Maybe on some level I’m seeing this as an opportunity to fix my family, which I know is impossible, but which I think all of us, somewhere, deep down, must long for. Do I break my word? How do I handle the aftermath if I don’t?

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A: Honor your word. Your brother has made his desires clear and any attempt to reconcile him with your family would be serving your interests, not his. You will regret not keeping your word to him if you bring in the estranged family members at this point. As to the fallout, you don’t have to let them know you knew. Or you can and state that they were as capable as you of reaching out. Everyone is an adult here and they’ve all made their choices.

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Q. Accentuate the positive: Please help! My best friend is getting married, I am the matron of honor, and her parents are paying for the wedding. I understand they feel this gives them a significant level of say in the wedding planning, but they have now, unsolicited, delivered to my friend and her fiancé personalized thank-you cards for them to write to the wedding guests that did not include her fiancé’s accent marks over his name! They did not even ask my friend and her fiancé if they wanted these thank-you cards in the first place, and they said they could not find anyone who “does” accent marks with letters.

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Overall, my friend’s parents are kind and well-meaning, but I do not think they understand how insulting and hurtful this is to the newlyweds-to-be. I want to find some additional stationery for them that spells his name properly! What else can I do to be helpful and supportive?

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A: Leave it be. If your friend and her fiancé want to get new thank-you cards, they can. But this sounds like something that doesn’t concern you, and inserting yourself in this will only make things complicated for your friend. Instead, you can be helpful and supportive by providing a listening ear and, when asked, serving as an intermediary for the other wedding issues that pop up.

Q. Thanks a lot, Putin: I moved from the U.S. to a central European country several years ago and I’m planning to have my wedding here in a few months. In order to help cover flights and other costs, I decided to invite only one friend from the U.S. (in addition to relatives).

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The thing is that since I invited her, the war in Ukraine started, and she’s understandably concerned about the situation here. My country doesn’t share a border with Ukraine, but we’re close to the conflict in the sense that there are already many refugees here, there are fresh memories among older generations of Soviet occupation, and I guess there could be fallout here in the case of a nuclear attack (though I think and hope that would be very unlikely).

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My friend asked me if I think she should still travel here for the wedding, and I honestly don’t know what to say. She wants to go, and seems really disappointed at the possibility of not traveling since this would be her first time abroad, so I don’t want to tell her no. But I also don’t want to say yes and then feel like I have some responsibility for something bad happening to her in the unlikely event that the war spills over here. What would you do in this situation?

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A: Unfortunately, neither you nor I can control war. Your concerns are very kind, but your friend expressed a desire to come to the wedding and is an adult who is just as aware as you are of the global political situation. If she wants to come, let her, have a wonderful time, and remember that the weight of the world isn’t on your shoulders.

Q. Re: Not smooth sailing: You’re 100 percent correct on the renegotiation, Prudie, but she can’t count a gift into the equation at all. That isn’t a household expense and the winnings don’t factor in either. She shouldn’t have paid for the cruise if it made her unable to contribute the agreed-upon amount in expenses. Don’t buy someone a gift you can’t afford and don’t hold it against them later.

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A: That’s fair. Gifts should always be free and clear of expectation. However, I suspect that the feelings around the gift point to a place where they may be misaligned emotionally. I think this couple thinks of money differently, and so when they renegotiate, which I hope they do, they’ve also got to bring all that extraneous stuff in, not as evidence against the other but as part of the complete emotional picture.

Q. Re: Thanks a lot, Putin: I agree with Eric about this being kind of out of your hands. I would only add that you should let her know that you will accommodate her decision, whatever and whenever it is. My house burned down three weeks before the out-of-town wedding of a close family member. She called to make sure we were all OK, and then very sweetly said that I could let her know as late as I wanted if I had to change my mind or decided I could take the weekend for the wedding. I really appreciated that.

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A: That’s such a good idea. Taking the pressure off the other person so they don’t feel like an imposition, no matter what they decide, makes a huge difference.

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R. Eric Thomas: Thanks for chatting, everyone! Be good to yourselves and others this week!

Don’t miss Part 1 of this week’s chat: I Found a Weird Way to Calm the Dog Next Door. My Neighbor Is Furious About It.

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From Care and Feeding

My 16-year-old daughter has been begging us to let her get a tattoo for at least a year. She just wants to get the birthdate of her (deceased) little brother on her shoulder blade, which I am, of course, extremely sympathetic to. However, her father and I have been extremely clear that she can get this tattoo when she is 18, and not before.

Well, last week she came home with a fresh tattoo on her shoulder blade.

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