Dear Prudence

Help! My Son’s 24-Year-Old Nanny Just Said She Has a “Serious Crush” on Me.

This is pretty awesome, but there are also a number of complications.

A young woman and a little boy reading a book together. The woman has illustrated hearts around her head.
Photo illustration by Slate. Photo by Getty Images Plus.

Our advice columnists have heard it all over the years. Each Sunday, we dive into the Dear Prudie archives and share a selection of classic letters with our readers. Join Slate Plus for even more advice columns—your first month is only $1.

Dear Prudence,

I am a 38-year-old widower. Three years ago, my wife passed away after a long illness. Our son was not quite 4. Since her death, my focus has been exclusively on him and my work. I have had no social life. My mother-in-law helps out, but she is quite old. I recently hired a woman to take care of my son until I get home from work. The woman is 24 years old, and my son adores her. She has a boyfriend of several years who seems like a good guy. Here’s the “problem.” She just told me she has a serious crush on me and is restless in her relationship. She has also made feints into discussions about sex with me, which I’ve brushed away. She is very attractive, and I have been completely alone since my wife passed, so this is pretty awesome on about 100 levels. But, of course, there are also a number of complications. I will not do anything if she is still seeing her boyfriend. If she does break up with him, what are my options? I pay this woman to watch my son. Does that arrangement end if I begin seeing her? If we eventually break up, can I (gulp!) hire her back? Do I sound as creepy as I feel?

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If your name is Von Trapp and hers is Maria, that would color my answer. But before you two burst into a chorus of “My Favorite Things,” I’m afraid pursuing this young woman, awesome though it may sound, is a bad idea on about 100 levels. It is perfectly understandable that you are eager to fall into bed with her; it’s about time you felt alive enough to pursue another woman. Since you’re already wondering whether you can hire her back when things don’t work out (answer: no), you clearly aren’t interested in her as more than a jumpstart to your too-long-dormant sexuality. Hooray that your sap is running again. So use the motivation she’s provided you to start looking for someone more suitable to date. This young woman has a pre-existing condition: She’s your son’s baby sitter. Both you and your son have been lonely and in pain since the terrible death of your wife. But he’s now made an emotional connection to this young woman, and it would be unnecessarily confusing for him to lose her as a baby sitter because you started an affair with her. I applaud that your response to her feints has been to brush them off and not to ravish her. Since nothing’s happened yet, keep it that way. You need to tell her that you appreciate the wonderful job she’s doing with your boy, and you want her to continue, but you two must leave your relationship strictly as employer and employee. If she can’t accept that, then you have to let her go. And now that you’re ready, you must put out the word with your friends—who have surely been waiting—that you’re in the market. —Emily Yoffe

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From: “Should I Sleep With the Nanny?” (March 4, 2010)

Dear Prudence,

I just think this is so bizarre, and I want an outsider’s opinion, so I hope you answer.

My niece recently got her septum pierced. I’m not one for piercings or tattoos, but it’s her body and her choice; it makes no difference to me. She also has several visible tattoos and multiple ear piercings. The trouble started a few weeks ago when she asked me to recommend her for a job at the hospital where I work. She’s a nice girl, so I said I would. But I warned her that the hospital has a very strict appearance policy. If she got hired she’d have to take all but one set of ear piercings out, cover her tattoos, and somehow cover up the septum piercing.

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Apparently what I said was interpreted as “mean and vicious.” She and her parents won’t speak to me and are posting on Facebook about how I “body-shamed” her. I tried to defend myself but just got slammed for my efforts, so I unfriended all of them. In doing so, they claim that I was “showing I knew I was in the wrong.”

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I’m totally at a loss here. Honestly, all I wanted to do was give my niece a heads up that if she showed up for an interview with visible tattoos and multiple piercings it might affect her chances of getting the job, and that she’d have to compromise her freedom of expression while on the clock.

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You are young. Can you tell me if I’m out of line and how to make things better (whether I was out of line or not)? Thanks.

I’ll take you at your word and assume you didn’t disparage her appearance or say, “Be sure to cover up your disgusting tattoos, you monster.” You informed your niece of the dress code at the hospital she’s interested in working at. That is not body-shaming. Disengaging from an online feud is not the same thing as an admission of wrongdoing, and it’s more than a little immature that your niece dragged her parents into her temper tantrum. You’re not out of line, and it’s not incumbent upon you to make things better. You politely acknowledged the reality of your workplace, and she threw a fit. Too bad for her. —Danny M. Lavery

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From: “Help! I Told My Niece to Hide Her Tattoos and Piercings at Work. Am I Body-Shaming Her?” (Apr. 11, 2016)

Dear Prudence,

I am engaged to a wonderful, funny, intelligent man, who, as we approach our wedding date, will be meeting more of my extended family and friends. I graduated from a prestigious university, and my family and friends usually assume that we either met there, or that he attended another notable school. However, he got his GED after dropping out of high school, and it embarrasses him when people ask where he went to college. He has a successful career, his lack of degree has never been an issue for us, and we know people only ask to make conversation, but it still makes him uncomfortable every time the question comes up. What is the best way to respond to spare him (and the asker) embarrassment?

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There are lots of successful people who just weren’t cut out for school—Richard Branson, for one. Sure, dropping out of high school is not the usual path to becoming a billionaire, but your guy has made a success of himself without academic credentials. It’s too bad he’s insecure about this. He needs to embrace his unique path and also put others at ease when they make small talk. You can help him. Tell him you know this comes up all the time and he shouldn’t feel self-conscious. When asked where he went to college, suggest he smile and say, “I didn’t. Heather and I met at a conference.” That way he will deflect the awkwardness and express his own comfort with his choices. —EY

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From: “Help! My Fiancé Is Embarrassed About Not Having Gone to College.” (Oct. 27, 2014)

Dear Prudence,

Some friends of ours adopted a dog a couple of years ago. The dog has some aggression problems with both dogs and people. We have a 4-year-old dog that does not have these issues. These friends recently had a baby, and the dog is no longer working out. They have been pressuring us to take the dog so it has a good home.

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We don’t want this dog; our dog is a show champion and stud, and we have plans to take a puppy of his instead of a stud fee. We also don’t want an aggressive dog! We said no, but the friends are very hurt and accused us of elitism. Any advice?

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Let your friends be hurt. They are only as wronged as they want to be. “We don’t feel safe taking a dog that you yourself believe to be unpredictable around a baby; this dog requires extensive rehabilitation and training that we can’t provide” is a perfectly reasonable answer to “Will you take our aggressive dog?” If your friends can’t see that, then no explanation, however rational, would satisfy them. They are looking to feel persecuted; don’t let them guilt you into endlessly justifying your decision. —DL

From: “Help! Our Friends Want Us to Adopt Their Aggressive Dog.” (Aug. 8, 2016)

More from Dear Prudence

My husband and his brother, who are close in age, were orphaned as toddlers. They spent their childhood shunted among family members and spent some time in foster care. They were sometimes neglected and abused, but thankfully they have grown up to have stable families. They are nearing retirement age. My husband lost his business due to the financial crisis and now works two jobs. Retirement is looking impossible. Several years ago my brother-in-law won the lottery, netting $50 million. He has bought several multimillion-dollar vacation properties and is living the good life. He and my husband have a good relationship and speak often. What I don’t understand is how he can stand to see his little brother so stressed and working so hard while he has more money than he could spend in a dozen lifetimes. Obviously he is under no obligation, but he does not seem to realize how hard it is to see how he spends his money on travel and amusements. I think he should help his brother out. What do you think?

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