Help! I Just Uncovered Something Deeply Troubling About My Old Mentor.

Dear Prudence is Slate’s advice column. Submit questions here.

Dear Prudence,

I recently went to dinner with a friend of mine and former mentor, Laura (57). A few years ago, I moved to the other side of the country, and moved back recently. I had been in touch with Laura sporadically and knew she’d divorced her husband and was dating someone younger. However, I hadn’t seen pictures of this boyfriend. Last week, Laura invited me and her boyfriend, Matt, to dinner. I had assumed Matt was in his forties when Laura said she was dating someone younger, but it turned out that Matt is in his twenties. I was even more surprised when I learned that Matt and Laura met while he was an intern at her workplace. At some point Laura mentioned that she broke up with her husband because she’d met someone new, but listening to their timeline, I realized she’d probably been having an affair with Matt when she divorced.

Matt struck me as extremely shy, awkward and immature. I was disturbed by their dynamic.
Laura used to be my mentor years ago (I’m 36), and I’ve now been thinking about several interactions I had with her when I was younger. I don’t think Laura ever took advantage of me, but I now have the unpleasant feeling she might have been testing the waters—and at the time I dismissed it as being friendly or ignored red flags. I’m fearing Laura may have tried to start romantic relationships with several interns or junior co-workers. I don’t know what to do. Should I tell someone at her workplace about this? I’m not positive Laura and Matt began a relationship while he was her intern, although I suspect it. I don’t really want to get Laura in trouble, but I also worry she may have crossed the line—if not with me, then with others, and that this might be a pattern with her. On the other hand, this is someone who was once a mentor to me and whose advice I valued. I don’t want to hurt her.

—Troubled Ex-Intern

Dear Troubled,

Laura definitely sounds like a creep who preys on younger and less powerful people in the workplace. Putting aside her possible affair, you just really cannot date an intern. You just can’t. Yet she did. You’re right to be disturbed and concerned. But telling someone at her workplace probably isn’t the answer. I say that because I’m just imagining the conversations would go like this:

You to Laura’s HR department: “Hello, this is a stranger. I want you to know that Laura may have started dating Matt while he was an intern and I now have the unpleasant feeling that she might have been testing the waters with me when I worked with her many years ago”

HR to Laura: “We wanted to talk to you about this complaint that we received.”

Laura: “Oh, I can explain. We actually started dating after he moved on. Yes, he’s younger, but it’s all above board.”

HR: “Thanks for that.”

See? There’s just not a lot to go on here.

The time to bring up your concerns will be if someone in your industry mentions pursuing an internship under Laura, or if you have some other opportunity to protect a young person from a potentially harmful professional situation involving her. Also, as I’m guessing you’ve lost a lot of respect for her based on these revelations, it’s fine to stop being available for dinners with her and her boyfriend/sexual harassment victim. You can just let the former-mentor-turned-friend relationship fade out.

“I would say they probably won’t do that but again, they’re asking for pens. So they kinda have a lot of nerve!”

Jenée Desmond-Harris and Joel Anderson discuss a letter in this week’s Dear Prudence Uncensored—only for Slate Plus members.

Dear Prudence,

Recently, my feelings for a close friend have grown deeper, with the increased time we’ve spent together. While I’m confident in his regard for me as a friend, I’m equally certain that he doesn’t view me romantically. Islam, my religion, is a fundamental pillar for me in envisioning a future partner. However, he approaches religions from an academic standpoint without practicing any specific faith. He consumes alcohol and eats pork, creating a stark contrast with the future I imagine. These feelings have left me torn between two difficult choices. On one hand, there’s the inclination to express my feelings despite the potential discomfort it might bring to our friendship. On the other, there’s the consideration that even if he were to reciprocate, I’m uncertain whether I could reconcile these differences, making any potential relationship seem unfeasible. The fear of initiating a romance that might be fundamentally unsustainable due to these disparities weighs heavily on my mind. Thus, I contemplate whether it’s better to create some distance, allowing myself the space to navigate and eventually move beyond these emotionally complex feelings.

—Feeling Lost

Dear Feeling Lost,

Keep this one to yourself. If you share your feelings, the best possible outcome is that you and this guy end up exactly where you are now, as close friends. But to get there, you would have to overcome the awkwardness of the announcement, the potential confirmation of his lack of feelings for you and the hurt feelings that might result or worse—the news that he loves you back but you two could never be compatible. He might even be offended that you would suggest initiating a romantic relationship while, in the same breath, giving him an ultimatum about him changing his diet.

Instead of going through all this, see what you can learn from the situation. Take note of the qualities that have made you fall for him and let them teach you something about what you might like in a partner who’s a better fit. I understand that when you have a crush, the person you’re into can feel irreplaceable, but I promise people there are other guys who are just as amazing as your friend and also pass on pork and alcohol. In fact, there are men who would not only follow the rules of your religion when it comes to what they consume, but also share your commitment to it, making your shared faith an exciting part of your connection. Spend a little less time with your current friend and go look for them.

Dear Prudence,

My mother remarried while my sister and I were in college; we never lived with her husband’s daughter, “Chelsea,” who was in her final years of high school. We would only see Chelsea on the occasional holiday and were never involved in each other’s milestones, like weddings and baby showers. This is why Chelsea’s over the top blow-up at our holiday gathering was so bizarre.

Before the holidays, my husband helped land a huge client and as a personal thanks, his boss offered the use of his tropical vacation home. With the bonus money, we could afford to treat my mother and her husband, plus my sister, to a vacation. (My sister is a middle school teacher and doesn’t make that much money. Our parents are retired.) We did get Chelsea’s kids gifts since they would be at the family gathering, but neither she nor her kids were included in the vacation offer. Chelsea got very upset and tried to pick a fight, saying that we ruined Christmas for her kids because they have never been on a “real” vacation before, and it was “cruel” for us to bring the offer up and not include them. It got so uncomfortable that her father had to intervene.

Now everything is sour. Our mother says that she and her husband won’t come because of how upset Chelsea got, and her husband would rather we give them the money we would have spent on their airfare so they can treat Chelsea and the grandkids. My husband says that will happen when hell freezes over. I don’t get the level of entitlement coming in from Chelsea or know how to deal with it in the future. And the kids didn’t even get upset. They were too busy playing with their toys. So what now?

—Vacation Woes

Dear Vacation Woes,

While it may have been a little insensitive of you to bring this vacation offer up in front of Chelsea at your gathering, you can sidestep this pretty easily: “Hi mom and stepdad. Can you let us know by [date] whether you plan to join us in Aruba? I’m sorry the vacation planning caused so much stress over the holidays, and if you decide to pass because of the conflict with Chelsea, we’ll understand, even though we would really love to have you. As far as the request to redirect the cost of airfare for other purposes, that isn’t something that will work for us. Anyway, a picture of the vacation home is attached. We were thinking you could have the bedroom with the king-sized bed and the patio facing the ocean. Let’s talk more about the details if you’re on board! And if not, let’s start thinking about a visit in the spring.”

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Dear Prudence,

I have a question about something that has plagued me for a few years. I am 32 and live in a different state from where I grew up. I have an older brother that has the same dad and mom as me, as well as two younger half-siblings (a decade younger) from my mom’s second marriage. Our mom died from cancer when I was 17. Her death really marked my life and it is still something I deal with to this day. My stepfather is a cruel, manipulative alcoholic, and I have kept my distance from him since my mom died. My younger siblings were 6 and 7 when mom died, and since I broke contact with their dad, a relationship with them was tough. Between the age difference, the fact that I couldn’t be around their dad, and then the literal distance when I moved out of state, I don’t really have adult relationships with them and we speak rarely.

They are now 21 and 22, and the youngest—my sister—got married last year. I was invited and attended the wedding to show support to her and her husband. Around the time of the wedding, our shared grandmother told me that my sister is often confused as to why we aren’t close, and why I “don’t like her.” It saddens me to hear that she is troubled by the distance, as she truly did nothing wrong, and it was more about me trying to protect myself when I was young myself. I don’t really see how we can have a relationship now: Aside from the age distance and the miles, we are on extremely different ends of the political spectrum, and I don’t think we have much in common. She is also close with her father, and I do not resent that at all—but also because of that, she has no idea why I never maintained a relationship with him. It was never appropriate for me to tell her how he treated me and my older brother. Some days I feel terribly guilty for not maintaining a relationship with my siblings, who endured the same tragedy as me, with an unstable father as their guide. Other days, I have compassion for myself since I was also young and navigating tragic circumstances. I guess I am left wondering if there is something I owe my siblings, who are now adults that I barely know. Any insight you have would be helpful.

—Not My Sister’s Keeper

Not My Sister’s Keeper,

Here’s a text or Facebook message for you: “Hi, I hope you’re doing well! How was the honeymoon and how’s married life? I wanted to reach out to you because Grandma shared with me that you were hurt by our lack of closeness. I need you to know you did nothing wrong and it’s not your fault. My relationship with our dad is distant and painful, and I’ve honestly never figured out how to work around that to get to know you well. I spent most of my younger years trying to protect myself and still struggle with some family dynamics. In other words, it’s not you, it’s me! Please share this with your sister if she has similar concerts. Your wedding was beautiful, and I was happy to be there to celebrate you, and I love to see your updates on Facebook. If you are ever in my area, please let me know and we should definitely get together.”

How do you manage working at home when your toddler knows you’re in the house?! We have a nanny so my 2-year-old is routinely at home. I work from home three days a week. On the two days that I’m in the office, she is fine with the nanny all day. On the days I’m home and in a different room, she’s a complete wreck. Having to leave the house to work in a different location seems to defeat the perk of working from home. Any suggestions?