I’m wealthy, and I want my girlfriend to quit her menial job: money advice.

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

Dear Pay Dirt,

I’m a 55-year-old divorced college professor who earns $140,00 a year (plus interest, dividends, and royalties). I have around $3.5 million in investments, home equity, and savings, so I am fairly well off. My 51-yearold girlfriend has little savings, works an hourly wage job, and earns around $40,000 a year (she’s had a much tougher life than me).

I would be happy to support us both and would like her to quit working (or work much less) so we can travel more and have more free fun time. But she is worried about losing independence and being financially dependent on me. She’s also worried about being perceived as a gold digger or sugar baby. I see her concerns as entirely legitimate. But I really want to be with someone who can, say, take a month off in the summer and go to Europe with me, go skiing for a week in the winter, and also go to the Caribbean for a beach vacation every year. This lifestyle is affordable for me (and I’m happy to pay—I don’t expect or need her to foot part of the bill), and it’s not uncommon among successful academics like me. But I know it’s also totally alien and unobtainable to many working/middle-class folks. This travel and fun are all very appealing to her, but there’s always the money/work/independence issue that seems to get in the way. We don’t really fight about this, but it is a key difference that is always present and creates tension. How do we bridge this?

—Want My Partner to Live the Good Life With Me

Dear Good Life,

Your girlfriend does not want to be dependent on you financially, a sentiment your columnist understands because she’s never wanted to be financially supported by a significant other, either. In light of this, she may be uncomfortable with the idea of you paying for things because she may feel it compromises the independence she’s trying to build.

Another factor is whether she likes her work. Not all working women want to work less or retire. So it seems as if the issue is that she doesn’t get enough vacation time for you to spend the time you want together, which isn’t surprising given that two weeks’ vacation annually is pretty standard (if paltry) for jobs in the U.S. Your girlfriend might not need to work less; she just needs a better paying job with more flexibility. But that’s her choice to make.

In the meantime, you should have a conversation about how you see your respective futures financially. Does your girlfriend want to keep working like this, or does she envision a long-term situation more similar to yours? How important is travel and down time to her? If her work hours and pay don’t accommodate these things now (and let’s be honest, an entire month off is pretty unobtainable for most people), does she think they will in the future? Because this conversation is really about the kind of life you envision together and not her work hours or disposable income, per se.

Dear Pay Dirt,

My father-in-law recently fell into a fundraising thing where he sends money to a person in Pakistan so they can get people out of indentured servitude. This began right after he retired. This whole thing has sent off alarm bells for my husband and his sister. I don’t think it’s unreasonable to think this thing might be legit, but the manner and speed in which it is unfolding is just odd. He is so obsessed with this that it’s all he talks about. He tells us about it over and over, like it’s the first time we are hearing of it. His passion is wild. He says things like, “We saved 150 people this weekend! Can you believe it only costs $140 to free someone?” He has used some of his own money and money that friends have donated to fund this.

The thing is that he has gotten my kids to want to shell out their own money to save other kids from indentured servitude. He found this person he is contact with in Pakistan on the internet. The man calls him at least three times a day to give updates. They FaceTime, and he gets photos of the ex-servants. My husband has just kind of shrugged his shoulders at this kind of stuff, but I don’t like seeing my kids get involved in the weirdness of it all. Should I just let my kids donate some money? They are very moved by this whole thing.

—The Kids Want to Save the Servants

Dear Save the Servants,

This sets off alarm bells for me, too. It’s possible that what your father is doing is legitimately helping people, but it sounds as if no one’s really checked. There are plenty of NGOs that do this kind of work, and you should be able to research the organization if it’s legitimate—if there is an organization, that is. It sounds like it might be one guy in Pakistan. If you father knows all of that and wants to take the risk, it’s his money, and he’s an adult, and while I think you can encourage him to explore other avenues for approaching this particular problem, you may not be able to persuade him to change course.

As for your kids, consider this an opportunity to teach them about how philanthropy works. If they’re old enough, let them research some charities that do this sort of thing and pick one themselves. Explain to them that your father-in-law is trying to help these people and there are many ways to do that. It can’t hurt for them to learn about generosity—and how to spot scams.

Dear Pay Dirt,

What do I do about my privileged brother who’s been living in our parents’ house for 25 years with no job? He got involved with drugs and booze in junior high, and my parents did everything for him, from putting him in “drug treatment” to taking care of his kids (he had two sons by an ex-girlfriend out-of-wedlock). Meanwhile, I minded my p’s and q’s—aka be little Miss Perfect. When he moved back home, our parents said that it was “for two weeks.” He pays no rent and no bills. Meanwhile, I’m on my own and broke.

—Tired of the Lies

Dear Tired,

I understand your frustration and know many people who’ve been in this situation. The problem child often gets the most attention. But ultimately, your parents’ decision to support (or maybe indulge or enable) your brother is their call. They certainly don’t owe him shelter and financial support, but they don’t owe you that either.

However, if you need and want help from them, you should ask directly. I doubt your brother hesitates to do that. But I wouldn’t hold out much hope that your brother, who seems to be unemployed long-term, will suddenly change his behavior, even if your parents decide to kick him out of the nest. It also wouldn’t necessarily mean they’d begin using those resources to support you. It’s not necessarily a zero-sum situation where you get nothing because your brother gets something. So you need to think about your brother’s situation as completely separate from yours in any discussions with your parents, because in their minds, it probably is.

Dear Pay Dirt,

I graduated undergrad with nearly $130,000 in student loan debt, because I had severe health issues throughout college that resulted in me essentially paying for two full semesters I did not attend, as well as what could have been better parental guidance. Nearly four years out of college, that looks like a $1,150 payment a month, which has essentially been a full pay check for my entire career. Looking at my career opportunities, I decided that the only real tenable solution was to go to grad school so that I can make significantly more money. I specifically chose a one-year program in the non-U.S. country I have citizenship in to try to keep the fees down as much as possible. I also applied to scholarships but am unlikely to get one, so it’s looking like I’m going to have to take out another very large chunk ($50,000 to $60,000) of U.S. federal loans.

I am confident that grad school is the right decision and will enable me to make more money and breathe a little, but taking out new loans is really bringing up all of the stress and anxious feelings I have about being so saddled with debt that I am usually good at tamping down. Barring any lottery wins or an extremely lucky career, I am going to be stuck with this debt into my mid-40s. How do I learn to be OK with it?

—Submerged in Student Loans

Dear Submerged,

I graduated with around $80,000 in student loans in 1999 and considered that a compelling reason not to go to grad school, even though I would have loved to. (In fact, if I ever win the lottery, I might go back to school, even though I don’t need another degree.) But plenty of people make the same bet you’re describing, in the hopes that the earning power of two degrees is exponentially higher than an undergrad degree alone.

But it’s not a given that an additional degree will net you more money, and it really depends on what you’re planning on going to grad school for.  There are certainly lines of work and study that would generate more income for you if your plan is to try to get yourself out of undergrad debt as quickly as possible. But do you want to get an MBA and become an investment banker? Or go to law school and become a corporate lawyer? You need to make a cold assessment of what your earning prospects are going to be with the specific degree you plan to get before you decide to accumulate more debt—particularly if the debt is what’s making you miserable right now.

It’s not inherently bad to hold student loans until your 40s. Barack Obama and Ted Cruz paid theirs off in their 40s, and they seem to be doing OK. But if the primary reason you’re going to grad school is to get in front of your undergrad debt, it’s a big gamble to take out even more loans. That said, federal loan programs are fairly flexible and will generally tie payment terms to income, so you’re not going to starve if you decide to do it. Just make sure you’re clear about your own motivations for wanting to go to grad school, and if money really is your primary motivation, make sure you’re very clear on what typical earnings are for people with your desired degree.


More Advice From Slate

I am a relatively young, male, and not-yet-tenured professor at a university. My department is overwhelmingly older (55-plus), white, and male. Several of the senior professors in my department, including the chair, have attitudes toward women that are downright sexist. On a number of occasions I have heard these faculty members make comments about the physical appearance of young women that are inappropriate and creepy. However, recently a female student confessed to me something that truly disturbs me. She said that two of the senior faculty, one of whom is the chair of my department, pays her for sex. She said she does not want to tell anyone else, partly for fear of getting in trouble because prostitution is illegal, but also because the two professors are essentially paying her college tuition in exchange for her services. I feel this is an extreme ethical violation, and judging by the character of the two professors probably only the tip of the iceberg. But I am at a severe power disadvantage in this situation. My boss can easily fire me. The dean and provost at my university are also member of this misogynistic “old boys’ club” and I don’t feel I can trust them. If the student refuses to testify, then the perpetrators can simply deny it and no one would believe me. What should I do?

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