Emily Yoffe, aka Dear Prudence, is online weekly to chat live with readers. An edited transcript of the chat is below. (Sign up here to get Dear Prudence delivered to your inbox each week. Read Prudie’s Slate columns here. Send questions to Prudence at prudence@slate.com.)

Q. My Sister’s Parenting: My sister has this idea that she shouldn’t confine her son to traditional gender stereotypes. Recently she started dressing him in feminine clothing. He is 4 years old and gets teased at his day care and has expressed many times how much he hates his dresses and pink tutus. She keeps telling him the other children are wrong to tease him and he should be proud of dressing that way. What can I say to her without insulting her parenting skills?

A: Your sister’s behavior will not have your son embrace her ideals of gender fluidity, it will make her boy turn against her and forever scar their relationship. My daughter was a decidedly un-princessy little girl. If at 4 years old I had insisted she go to school in a tutu, she would have ripped it off and refused to leave the house. (Even in nursery school she picked her own outfits and one of my favorites was the Tyrannosaurus rex sweatshirt and pearls.) If your nephew insisted on wearing a pink tutu and was teased because of it, that would be an understandably difficult situation, but one that everyone could work on together to make her boy feel happy and secure. But what you are describing is a deranged attempt by your sister to impose her views—or even work out her issues—literally on the back of a small child. I hope you have some influence with your sister and can tell her that her ideals are lovely, but children need to have their own identities and it’s painful to see your nephew so miserable because he can’t wear the normal boy clothes he desires. If she won’t see reason, then it is reasonable for you to privately contact the head of the day care center and ask her to try to intervene with your sister, explaining her son’s misery over his clothing is stunting his social development.

Q. Demented Director?: The director of my division at work is in his early 70s and I have noticed he seems to have speech and memory difficulties that are getting worse as time goes on. It has caused some problems where he is unable to remember important facts and also in communication with upper management and clients, although nothing devastating (yet). I’m considering bringing up my concerns with my direct supervisor, who has known him for over 20 years. Should I do this or just wait for him to decide to retire?

A: Having someone in, say, a fiduciary position who is no longer mentally competent is creating a legal risk for the company. It may seem like a kindness to ignore that this man is failing, but it’s not. Note instances of what’s going on, then go to your supervisor or HR and say it deeply pains you to have to report this, but you are worried about the mental status of your director, and he needs a medical evaluation.

Q. Family Secret—I Might Be the Only Person Who Knows: In 1962 my older sister and I shared an apartment for a summer. We became very close. I had just broken up with my boyfriend. A year previously she had been dumped by her boyfriend when she got pregnant with his child. She moved to another state (not telling anyone in my family she was pregnant), had a boy, and placed him up for adoption. She asked me not to tell anyone, and I have not. She later married, had a child (a boy), and unfortunately died when her son was 10. I have never been close to my brother-in-law or nephew as they live across the country. I wonder 1) if the son my sister gave up for adoption has searched for her family; 2) did he find my brother-in-law who hasn’t shared the information with my family; 3) do I broach the subject with my brother-in-law, and if so, how? or 4) do I search on my own for my nephew, and if so, how?

A: First of all, you have a nephew you don’t have to search for—he’s there across the country, disconnected from his mother’s family. Unless something happened that caused an unbreachable estrangement, it is very sad that you have lost touch with your sister’s son who probably would like to know more about his mother and her family. If you’re going to start doing reaching out, please start there and get to know your nephew. As far as your unknown nephew is concerned, you could do your own search. There are various registries for parents who placed children and children looking for biological parents (and relatives). Maybe this now-middle-aged man has your sister’s name and has been trying to find her. If so, you can answer his request and fill in some holes in his family history.

Q. Missing Teeth: I am a woman in my late 30s who has survived two serious illnesses. I am lucky to be alive and healthy. About six months ago I met a great guy, and I see a future with him but I have a big secret that I’m not sure how to mention. One of the treatments I had caused great damage to my teeth. The dentists tried to fix and save them but ultimately I lost about 10 of my teeth. I now wear a partial plate in my mouth that is fairly unnoticeable but it’s become a worry for me as to how to tell the guy I’m seeing about it. I know I look horrible without it, and so he’s never seen me without it in. I’m scared to tell him. I really like this man, we are skirting around the L-word but I’m afraid he won’t even want to be with me because of this. What should I do?

A: I hope you haven’t been hiding the fact that you are very lucky to be alive, and I hope his response to this is has been that he’s lucky, too. In that context, your partial is a very trivial thing. Sure, it’s big to you, but it’s so cosmetically effective that he hasn’t even noticed. So what you do is tell him. I suggest you start with, “There’s something about myself I haven’t told you and I really need to.” This will get him thinking all sorts of horrible thoughts: You’re married, you murdered your last boyfriend, you’ve exposed him to Ebola, etc. When your next sentence is, “I wear a partial denture because one of my medical treatments damaged some of my teeth,” he should feel great relief. I hope he let’s you know it’s no big deal, and that you can feel grateful that a denture is a small price to pay for being here to enjoy the rest of your life.

Q. Re: Family Secret: I work at an adoption agency, both in helping to place children with a family and in helping adopted children find their birth parents, or vice versa. You get a lot of questions regarding adoption in this column, and I would like to clear up a misconception: Many states have pretty strict adoption laws that make it very difficult for anybody other then the birth parent or the child to find relatives. While your advice is decent, this LW needs to accept the fact that chances are very good the bureaucracy of adoption means that she is not eligible to find this child. It seems, in this column, that people are under the impression that anybody who is related to a birth mother or an adoptive child have an automatic right to these records and that is not the case.

A: Thanks for this clarification, but aren’t there nongovernment registries where people go to try to find each other? I was suggesting that the aunt perhaps put her sister’s name on one of these and see if she is contacted by the nephew. There are lots of ways outside of official channels for family members who want to look for each other to start searching.

Q. Job Recommendations: I have my dream job, working for a cable TV network that has a lot of rabid fans. Because of this, I am constantly getting requests from friends, friends of friends, and friends’ mothers’ accountants, etc., all wanting help getting a job there. I’m always happy to put in a good word and/or pass on a résumé and cover letter to HR if I think someone’s talented, and I’ve done this a few times for close (qualified) friends since I started. But thanks to social media I get these requests almost daily. (My manicurist’s brother has a brilliant idea for a new TV series! My cousin’s daughter just graduated college and would be perfect for an internship!) I simply can’t help all of these people … partly because I’m not high enough in the ranks, partly because I need to maintain my own reputation, and also partly because I find this pretty presumptuous. What’s a polite way I can give a firm, understood “no” without being rude?

A: This gives me the opportunity to tell you about my idea for an HBO series about an advice columnist whose live chat, which she does at home, is constantly being interrupted by the bathroom needs of her dog … excuse me, I’ll return in a sec. OK, back to your question. If you have a résumé from someone who is so good your bosses would be grateful, then you directly pass it on. Otherwise you memorize the email address at your company’s website that anyone can use to apply for a job, and you say they need to send a cover letter and resume to that address. When they press you for a personal hand off, you just shake your head and tell them you’re so low on the totem pole, you wouldn’t even know whom to speak to.

Q. Husband Not on My Side: I’ve been married to a wonderful man for almost a year now. He’s great with the kids. Not only does our 10-month-old love him, so does my 10-year-old and 6-year-old from my previous relationships. The problem is I have to threaten to leave him in order for him to take my side on issues with others. When we got engaged, a few friends of his started sending me insulting Facebook messages about our relationship. When I mentioned this to him, instead of doing something about it, he just told me to ignore them. When I told him that I wanted him to remove them from his life, instead of doing so, he wanted to talk to them. It wasn’t until I threatened to leave him that he begrudgingly removed them from his Facebook and phone. It then happened again after we got married. His dad and brother started pestering me through Facebook with snide remarks and other insulting posts. Like last time, when I told my husband, he first told me to ignore them. Then when I asked him to choose between them or me, he said that he wanted counseling for us. I shouldn’t have to threaten him for him to give me my place. How can I make him see that when someone insults me he should take my side and leave them behind?

A: Either you’re paranoid or you have a way of making enemies. Frankly, from reading your one paragraph, I’m not too crazy about you. Get off Facebook. Maybe you inspire people to post insulting comments about you, or maybe you read insults into run-of-the mill remarks. In any case, you don’t have the temperament for social media, so instead of trying to force everyone else to unplug, you should do so. Also, immediately take your husband up on his offer of counseling. You just had a baby with this man and now you are getting into showdowns with him over the future of your marriage. You’ve got three children by three men, so if you want to stick where you are and have this good man be a father to all your kids, you will address with a professional some serious problems you have in getting along with others.

A: Thanks, everyone. Talk to you next week. Look for my HBO series: “I Let The Dog Out, Again.”

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