Dear Prudence

Help! Our 50-Year-Old Friend Says He’s Fallen in Love With Our 19-Year-Old Daughter.

Read what Prudie had to say in Part 1 of this week’s live chat.

Young woman on the left; two people loosely holding hands at right.
Photo illustration by Slate. Photos by Craig Whitehead on Unsplash and Dan 7Kidz on Unsplash.

Daniel Mallory Ortberg is online weekly to chat live with readers. Here’s an edited transcript of this week’s chat. 

Danny Ortberg: Good morning, everyone, let’s chat!

Q. “Uncle” is falling in love with our daughter: A college friend has long been an “uncle” to our two children. He has been there for school events, milestones, vacations, etc. Our daughter went away to college this year, to a town about 45 minutes from this friend’s house. He volunteered to look out for her, take her off campus for movies, send her mail, and drive her to and from our house for various events. The other day, our almost-50-year-old friend admitted that, for the past five months, he has been “falling in love” with our barely 19-year-old daughter. He says this is not OK and that he’s been trying to prevent the feelings, though he has not reduced his interactions with her.

He asked my husband and I not to tell her so their relationship wouldn’t become awkward. We’re floored. We told him we’d have to tell her, and he’d have to cease all contact with her. I feel intensely angry, betrayed, and suspicious. We haven’t told our daughter yet because we want to do it face-to-face after her finals have ended. What do we do going forward? How can we ever trust him again? Should we? Do we tell our son? Mutual friends?

A: That is tremendously distressing, not least because your friend decided to unburden his feelings onto you while also refusing to limit the amount of time he spends with her. That he told you while asking you not to tell her demonstrates astonishingly bad judgment, not to mention selfishness. He expects you to, what, calmly absorb this information while he continues to deliver your daughter’s mail to her and “show her around town”? He’s asking for your implicit approval in order to continue to court her without her knowledge, and you’re right not to countenance that request. I’d hold off on telling your son until you’ve spoken to your daughter in person. This may be shocking and deeply upsetting to her, and she has a right to decide who she’s comfortable with your speaking to about the subject.

The arrangement he suggested in the first place was not a good one—it’s one thing for a family friend to give a college freshman a ride to family events and let her know the best place to do off campus laundry, but it’s another thing for a 50-year-old man to volunteer to regularly take her off campus to go to the movies one-on-one. I think his offer of helpfulness went above and beyond the normal “friend-of-the-parents” call of duty because he had designs on her from the start. I don’t buy his story that he suddenly and without warning fell in love with your daughter because they happened to be thrown together. I think he’s deeply untrustworthy, and it’s monstrous that he’s asking you to lie to your own daughter in order to preserve her misplaced trust in him. I’m so sorry you’re dealing with this sudden revelation about the character of a man you’ve trusted for years, but don’t let him snooker you into thinking this “just happened” or that the worst thing that could happen now is his relationship with your daughter could “become awkward.” Most college freshmen aren’t champing at the bit to go to the movies with their parents’ friends. Had avoiding awkwardness really been his concern, he could have placed boundaries on his relationship with her himself the second he noticed his own interest becoming something other than avuncular. He instead went out of his way to be “helpful” at every turn, and then announced his feelings to her parents. He does not have her best interests at heart.

Q. The boys’ Cinderella: I am 20 and feel more like a housekeeper than a daughter and sister. My stepmother walked out of our lives without a word, leaving my stepbrothers and half-brother behind. We don’t know where she is. This happened when I was 14, and since then I have had to be “the woman of the house.” All the cooking and cleaning fall to me, even though all the boys are in their teens. They will not pick up after themselves and prefer to sleep and play video games. I fight with them about this all the time. My dad takes their side. He says I have to be more responsible because I’m older and he doesn’t have time to deal with my drama.

I work and go to school. Sometimes I get so tired, I come home and just cry. I have lost all my friends since I have no time for them. One of my classmates offered to let me move in with her on a reduced rate. I want to do it badly, but I know the house would fall apart without me. I told my dad, and he yelled that I was just like my stepmother for abandoning my family. My brothers also got upset with me. They promised to change, but that hardly lasted two days. I love my family, but I feel trapped. What do I do?

A: Move out. You have put yourself through the wringer a number of times for them, and they’re not going to change. The house will not fall apart without you. What will happen is that your father and your brothers will squabble and then figure out a way to continue surviving. Either the house will become a lot messier, which will not kill any of them, or they will find it worth their while to pick up after themselves. These are not little children who require constant care and supervision. They’re nearly grown, and you don’t have to do their dishes for them just because you’re older and your father has abdicated his position as the responsible adult in the house. The difference between you and your stepmother is that children are supposed to grow up and develop their own lives. That your father would try to use her as a reason for you to stay is more than a little creepy and totally inappropriate. Move in with your friends, enjoy your college years, and don’t get sucked in by their attempts to guilt you into coming back and reminding them what hand towels are for.

How to Get Advice From Prudie:

• send questions for publication to prudence@slate.com. (Questions may be edited.)

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

• call the voicemail of the Dear Prudence podcast at 401-371-DEAR (3327) to hear your question answered on a future episode of the show.

Q. Re: “Uncle” in love: Seriously? They are both adults, let them manage this like adults. If she wants to date him, or have sex with him, or cut off contact with him, that is her business.

A: They are not “both adults” in a number of real and meaningful ways. She is 19, he is pushing 50. A year ago she was in high school, a year ago he was in his late 40s. She is a college freshman who has never lived independently, and he’s a grown man who’s acted as a relative to her for years. To call them “both adults,” as if there weren’t a very real power imbalance between them, is an elision of reality.

Q. Bridging the knowledge gap: Both my daughters are complete bookworms. They are intellectually gifted and have skipped grades, and we have college students coming in every week to tutor them. My mother and sister cannot relate to them. At all. I know they love them, but they interact with them like they have never had a conversation with them. For gifts, my sister and mother give them dolls and Disney princess outfits they will never wear. They tease them about boys “liking” them or talk over them when my girls express interest in science or books. It is frustrating because I can tell my girls prefer my wife’s family over mine. They get animated and excited if my in-laws are coming. I tried to explain this to my mother and sister, but I ended up putting my foot in my mouth and offending them. Neither of them is what I would describe as intellectual, but they are good people. I am worried that my girls will grow up without that important influence. How can I bring the ladies in my life together happily?

A: It sounds like your girls are growing up with lots of good influences, so I think you can rest easy, at least in part—they don’t seem in any danger of being neglected or of having their dreams belittled out of them. I do think it’s worthwhile to continue pushing back against your mother and sister if they ignore your daughters when they’re talking, or attempt to turn conversations repeatedly to what boys might like them, but I don’t think you can—or should—have as your goal “make sure my daughters like my mother and sister as much as I do.” They’re going to develop their own relationship with your mother and sister, and if they ultimately have a marked preference for your wife’s relatives, then that’s a pretty common, everyday occurrence in families. You can make sure they see one another regularly, you can love them all independently, and you can hope for the best, but you can’t force closeness where none exists. You also can’t hurry affection, but it may come with time as the girls get older and your mother and sister continue to try to find other ways to relate to them besides getting them presents they don’t like.

Q. Third wheel at work: My two closest friends at work have started hooking up. We’ve all been working together for over three years now, and they’ve been getting closer, hanging out a lot outside of work. I mostly just hang out with them at work—we’ll get lunch and go for walks in the afternoon—but occasionally I’ll hang out with one or both of them outside of work. Their banter was always been flirty, but until recently one of them was in a relationship. As soon as the coupled girl broke up with her boyfriend, the two of them started hooking up.

How do I navigate this? I’m annoyed, honestly. It seems like it will cause drama, and I was already feeling like a third wheel when we hung out. I definitely don’t want to hang out with them together anymore, but I also don’t have a problem with them individually and would like to be able to keep the individual friendships. Is that possible? I’m going to be declining lunches, and hopefully just taking my own walks instead of going with them, but they will probably notice if I just stop all group-hanging.

A: Taking a step back seems like an eminently sensible idea, and I hope the two of them will get the hint and start setting firmer boundaries between how they treat one another at work in front of their colleagues and how they flirt with one another after hours. (I don’t think they’re likely to get any hints, given that they’ve already demonstrated more than a little short-sightedness on the subject, but one can still live in hope.) If either of them tries to push the issue or asks why you’ve started scaling back, you can say something bland about trying to refocus on your projects at work and socializing a little less. If they still don’t let up, then you can say, “I’m happy for you, but there are a number of potentially uncomfortable outcomes if things don’t work out, and I’d rather not get more involved in your romantic relationship than I have in the past.”

Q. How do I quit?: I thought I was friends with “Jessica.” We talked a lot at work, and I was very sympathetic to her plight as a single mom. I offered to babysit her son if she needed me. Jessica took me up on that, but I feel I am no longer a friend, only a free babysitter. Jessica no longer works with me, and in the three months since she’s switched jobs, I have gotten texts about her leaving her son with me for a few hours at least three times a week. She always makes these plans on short notice. He is a good kid and loves to play with my dogs, but I want to quit. Jessica never makes plans with me or asks me about my life. She goes out on dates, does errands, or goes out with other people. The few times I have gotten her to agree to an outing, she has canceled on me. Jessica is very charming, and I am not very good at talking with people. I have tried voicing my concerns to her, only for her to turn the tables on me and make me feel like an idiot and a bad person. How do I quit this friendship that isn’t a friendship?

A: If you want to quit being friends with her, then don’t voice your concerns, just announce your resignation. Say, “I’m not available to babysit anymore,” then decline to get drawn into an argument about the subject. If she tries to turn the tables on you, then end the conversation; since you’re not interested in maintaining her good opinion, it hardly matters if she takes the news badly.

Q. What do I owe my ex–real estate agent?: Two years ago, I used a buyer’s agent to assist with the purchase of my home. He did a fine job, but my partner felt like he was a bit untrustworthy. Nothing bad happened, my partner just got a bad vibe and was brought up to not trust people in sales. We recently sold this same home using a different agent. Now the first agent has emailed me and my partner, CC-ing his boss, to ask why we didn’t use him. He has called me and texted me as well. I don’t really have anything constructive or substantive to offer him—I happened to strike up a conversation with the new agent, and my partner was more than happy to try someone new. Without having anything useful to tell the old agent, I’d rather not say anything at all. Can I just ignore these messages? On the one hand, I don’t feel that I owe this person anything, and I really don’t want unnecessary confrontation in my life. But the flipside is that I hate being ignored personally, so I’m loath to do it to someone else.

A: If you don’t want to totally ignore him, just send back a brief email that says, “I happened to find a new agent who suited my needs; you did a fine job when I purchased my home, and this was not a reflection on your work.” Then ignore him.

Q. Grieving strangers: A client had to cancel on our meeting due to the loss of a family member. We’ve only had two interactions at this point, so I barely know this person. How should you respond back to an email informing you of something like this? Saying, “I’m sorry for your loss. Can we reschedule for next week?” seems too rude, but since we’re relative strangers the usual platitudes seem inappropriate. “You’re in my thoughts”? Not really. “If you feel like talking, I’m here for you”? Please don’t. “He’ll be missed by many”? I don’t know this person. What’s the polite thing to say?

A: “I’m sorry for your loss” is just fine, but instead of suggesting a time to reschedule for—since you don’t know if they’ll be planning a funeral or dealing with other family members—say instead, “Let me know if you’d ever like to reschedule. I’ll be available, and hope you’re looking after yourself.”

Q. Update—“Uncle” in love: Since I originally wrote, our daughter has come home from college. We told her, and she was surprised and skeeved out. She says she honestly had no idea. We told her we’re no longer allowing contact from him, and that she should let us know if he tries to reach out. The friend has since blocked us on social media. My husband says he will reach out occasionally, in the interest of our decades-long friendship, just to make sure he is getting some help. Thanks for validating our feelings on this one.

A: I’m glad you’ve talked to your daughter and that you have a plan in place should he attempt further contact. I’d encourage your husband to consider what he means by making sure his friend is “getting some help.” What would help look like in this case? How might it feel to your daughter to know that her father is still periodically in contact with this man? What actions would this man need to take that would demonstrate a good-faith effort on his part? The temptation to normalize and excuse a long-time friend’s behavior may be a strong one, but the level of his deception, the wildly inappropriate nature of his disclosure, won’t be adequately addressed by a few months of therapy and an assurance that he’s “all better now.”

Q. Update—Wireless in the woods: I’m the letter writer with the rural internet situation. We appreciate all the advice from you and commenters! My husband told the cantankerous neighbor that we would let him on to the private network we set up if he 1) granted the easement (in case the phone company ever comes back), and 2) paid $2,500 in setup cost. We did not explain where we came up with this number, just asserted it (it comes out to about 25 percent of the cost we incurred on the project). He immediately accepted, with gratitude.

A: I did not expect such a universally pleasing outcome, but it goes to show that every once in a while, “Just ask—the worst thing anyone can say is no” is a pretty useful strategy.

Discuss this column with Dear Prudence on his Facebook page!

More Dear Prudence

I’m Afraid My Mother Is Going to Disrupt My Friend’s Wedding.
It’s Annoying When My Hypersensitive LGBTQ Friends Make Fun of My “Vanilla” Sex Life.
I Ran Over and Killed My Neighbor’s Toddler. I’m Overcome With Guilt.
My Roommate Won’t Let Me Shower With My Boyfriend
Why Do My Girlfriends Always Think I’m Still in Love With My Ex-Wife?

And find even more letters in the Dear Prudie archive.