Help! Our Daughter Already Wasted a Huge “Business Loan.” Now She’s Blackmailing Us for More.

Dear Prudence is Slate’s advice column. Submit questions here. (It’s anonymous!)

Dear Prudence,

Our daughter had a terrible first marriage. Her husband was a narcissist and a liar. We gave them over $50,000 in what was supposed to be a business loan. The money went to fund a lavish lifestyle, and when that crashed and burned, my daughter parroted whatever her husband said and claimed it was a gift. She cut us out of her life for two years after we made noises about seeking legal counsel. We ended up writing off the money, but privately agreed that while we wanted a relationship with our daughter, we would never be put in a position like that again. Our daughter came to her senses and divorced her husband after he got in serious trouble with the law. We welcomed her back and never mentioned the money, until now.

Our son and other daughter are getting married and looking for a new house, respectively. We are paying for it. Neither has asked us to support them since they graduated college, so it seems only fair. Our daughter caught wind of the arrangement and is now demanding we similarly help her out. She is engaged again, but neither makes much money. We reminded her of the original fifty thousand and she cried, saying she couldn’t believe we were “throwing that in her face” again after everything she has been through. We don’t want to lose her again, but neither do we want to give into blackmail here. What should we do?

—Money Matters

Dear Money Matters,

I don’t really see where you’re being blackmailed, but I understand that this must be very tough, and that everyone’s traumatized by your daughter’s awful first marriage. I don’t think this is what you want to hear, but if you can afford it, why don’t you go ahead and give her a gift equivalent to the wedding and down payment gifts you’re providing to her siblings? Hear me out! The 50k you gave her was a business loan. Sure, it was a loan that you ultimately had to write off, but it seems most of the blame for that was on her narcissistic, lying, criminal husband, who I’m guessing was manipulating her pretty intensely. So she’s actually never had the “Here’s a chunk of money from your parents as a gift to help you get started in life” experience that her siblings are about to enjoy. And right now she could really use it. I don’t like that she “demanded” the money. That’s entitled and obnoxious, definitely. But if you can keep in mind that she’s had a really hard time recently and forgive that (and again, if you have it sitting around), why not?

Now, if it’s the case that you had an account with 50k earmarked for each kid and drew from that when she and her ex didn’t repay their loan, she’s out of luck.
The money simply isn’t in there. I’m hopeful that if you explain that clearly, without throwing in anything judgmental about her bad romantic choices, failed business, or lavish lifestyle, she’ll be able to move past her disappointment.

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Dear Prudence,

I (39M) have been close friends with my current girlfriend (38F) since our mid-twenties, although we didn’t start dating until just a few years ago. Our relationship is fairly casual in terms of life markers (we do not live together, nor do we plan to; we do not want to have children together, and our finances are separate), but emotionally intense. Our connection has from the start been deeply entwined with mutual artistic creativity as well. I care deeply for her and have never met anyone that I have felt so mentally and creatively attuned to. I have dated other people during the time that she and I were only friends, as did she, but we have both acknowledged to each other that during that time we were mentally holding up all our partners and comparing them against the way it felt to be together, and finding those comparisons lacking.

When we spend time together, it is always wonderful—everything from deep excited creative sprints, meandering philosophical conversations, amazing sex, or comfortable quiet cuddling on the couch to watching a movie or just existing with each other in pure contentment. Basically, I love her intensely and want our relationship to last in more or less its current configuration for the rest of our lives, and she has repeatedly expressed her reciprocation of these feelings. It is very difficult for me to imagine finding another person like her in the whole world, let alone one who also does not possess the traits of hers I have qualms about.

And Prudie … boy, do I have qualms. I consider myself to be an easygoing, flexible, and generally tactful person; she holds to a philosophy that tact is just a nice name for lying, and is very exacting about wanting things her own way all the time. While she is willing to compromise if I push back, it takes a lot of energy to negotiate compromises with her. Our compromises are generally harmonious when I care enough to spend the energy, but because I’m almost never as firm in my expectations and requirements as she is, I wind up giving way most of the time because it is simply easier for me to flex around her than to try to make her bend even a little. She also maintains a carefully private and locked-down social media page that only I and a few other very close friends have access to, in which she speaks very cruelly about her current roommate/former girlfriend and other people (her father, her younger siblings + nieces/nephews, other close and mutual friends) and makes it clear that if someone doesn’t know something she considers obvious, she believes them to be at best idiots and at worst deliberately refusing to understand her.

While she has the capacity to be deeply kind and supportive to people she cares about, and has come through clutch for me and other friends on a number of occasions, she also has the capacity and willingness to be very cruel. And I know already that she will not take feedback about this cruelty; she believes her treatment of others to be justified, and believes that keeping the ranting to a private space is a sufficient concession to social harmony. However, she has shared screenshots of text conversations with these people, and she speaks to them in much the same way she writes about them; she’s very harsh and does not consider that people have different perspectives and knowledge bases than she does. Basically, deep down inside I have a sinking feeling that our relationship is only this good because I’m carefully avoiding anything that looks like conflict with her. I’m not sure this is a wise or legitimately sustainable relationship. There is a part of me that thinks there must be a relationship out there with someone I wouldn’t have all these qualms about, but I don’t see a point in dumping my girlfriend “on spec” of something better maybe existing.

Fundamentally, this is my question: Is it better to date someone who I love intensely but also have reservations about (so long as she continues not to unleash her cruelty on me directly or cross some as-yet undefined line of cruelty to others), or should I work on extricating myself from an intense involvement with someone whose expectations and treatment of others I sometimes find deeply troubling?

—Concerned

Dear Concerned,

That sinking feeling is right. You wouldn’t be dumping her “on spec.” You’d be dumping her because going through life avoiding conflict with a person you see as cruel, controlling, and narcissistic sucks and is no way to have a relationship. But for what it’s worth, yes, there is someone out there who isn’t this mean.

Dear Prudence,

I have a dilemma at work that I’ve left to simmer for too long, and now I’m about to burst. I am white in a very diverse workplace for a very diverse public university. One of my coworkers has been using the word “herro” instead of “hello” CONSISTENTLY for the ENTIRE year and a half I’ve been here. The only reason I haven’t said anything? She’s Asian. But it’s starting to eat at me because I know she is Chinese. And my understanding of the word “herro” is that while it was originally perhaps used to make fun of anyone with an Asian accent, it was derived from specifically the Japanese accent in that “l” sounds don’t exist in Japanese and are substituted with “r” sounds. As someone who taught English in Japan, I know for a fact that the “l” sound is really, really hard for native Japanese speakers! And my Chinese-Canadian coworker has a Canadian accent—i.e. she was born and raised in Canada, English is her first (or primary) language. So every time she says it, I cringe.

I really hate to be a white person policing Asian use of a word that was used to make fun of Asian language speakers. But I am starting to feel like I’m betraying my Japanese friends, former students, and the Japanese population of our school by not saying anything! Asia is not a monolith and what is offensive to Japanese speakers may not be offensive to Chinese speakers. I’m pretty certain I should say something, so I guess my question is: 1) Should I bring it up to her manager and ask the manager to speak to her, to avoid complicated office politics (which are SUPER complicated at this time, not the least because this coworker is technically my superior and takes feedback poorly)? 2) If I should bring it up myself, what’s my script so I don’t come off as a preachy white busybody?

—Should I Stay or Should I Go?

Dear Stay or Go?

I started to fact-check this letter to get a better understanding of whether there was a legitimate concern about your colleague’s pronunciation offending the Japanese population at your school. And then I started to read it over to try to figure out whether you think she is doing this intentionally or not. But then I stopped because it doesn’t matter that much. While the issue you’re worried about may be real, this isn’t your business, it isn’t affecting you directly, you don’t manage this woman (in fact she’s your supervisor!), no one has complained to you, and you already know that your feedback wouldn’t solve the problem.

So I have a script, but it’s for you to say to yourself: “My strong reaction to the way my colleague says this word is a reminder of how much I care about making this university an inclusive place.
I am going to be strategic about how to do that in ways that match my role here. There are many cubs and affinity groups here who might appreciate my support, and there will be many moments in which my voice as a white person is powerful. I will look for opportunities to be an ally. When it comes to standing up for marginalized groups, I’ll follow the lead of the people who I hope to protect.”

Catch up on this week’s Prudie.

I came home last night after a girls’ night out and noticed that my husband’s phone was not plugged in. I picked it up, plugged it into the charger and took a peek to see what’s happening on Facebook. I open it up and there I see a picture of one of his friends in a bikini, zoomed into her body and chest. I woke him and asked him about it, and he, in a sleepy daze, admitted that he used it earlier in the night to masturbate to. I can honestly say I lost it.