Dear Prudence

Dress-Up Dilemma

In a live chat, Prudie counsels a woman whose husband forbids their toddler son from putting on her shoes.

Emily Yoffe.
Emily Yoffe

Photo by Teresa Castracane.

Emily Yoffe, aka Dear Prudence, is on 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

Emily Yoffe: Good afternoon. I look forward to your questions.

Q. Boys Will Be Boys: I have a 19-month-old son who is an all-around joy! He has taken to the habit of putting on the nearest pair of shoes, grabbing his diaper bag and my keys, and pretending as if he is about to go bye-bye. He usually puts on my shoes because my husband’s big shoes are much too heavy for him to walk in. My husband has taken issue with him wearing my shoes (generally ballet-style flats) because he doesn’t think that a little boy should play dress-up in women’s shoes. I don’t care if he plays in them, and although I don’t believe at this age he knows the difference in gender-bearing apparel, I would not care if he did. My husband, however, makes him take them off, often prompting an emotional response from my son. My son’s hysterics then cause my husband to make him sit until he calms down. We’ve argued about this issue so much. I see no harm in letting a child explore his curiosity and imagination in this nonharmful way. My question is how do I get my husband to lighten up about it? He is from a culture where males are supposed to display typical male gender roles and characteristics only.

A: Please enroll together with your husband in a parenting class—many YMCAs have them. You want this to be a joint experience for the two of you. You want to avoid sounding as if you are sending your husband alone to the dunce’s corner, no matter how much he may belong there. I totally agree that your 19-month-old is doing what every toddler is programmed to do, that is imitating his parents, the most important people in his life. Your husband’s overreaction to his son’s sweet and charming behavior is crushing and confusing. Since this is a recurring problem, look with your husband at the Gesell Institute website which has lots of material about children’s developmental stages and what to expect. I also will reiterate my recommendation of Haim Ginott’s Between Parent and Child, a book that really helps a parent understand a child’s mind and respond with compassion. You do not want to set up a dynamic in which you attack your husband’s culture—you married him knowing what it was, and presumably that he embraced some of the tenets. Instead you want to examine how some of these beliefs affect your family, and work together so that all three of you treat each other with gentleness and respect.

Dear Prudence Classic: Kinky Mom

Q. Background Check on Questionable Fiancé?: My younger sister is engaged to be married to someone she only knows from online and has never met. They’re planning on meeting when she drives out east to help him move into her apartment back on the West Coast, and marrying around the holidays. We know nothing about this guy. No Facebook, nothing. But she is very trusting and gave me his name and birthdate and I know which state he lives in. Should I have a background check run? I am willing to take the risk that she’ll hate me forever if I can at least check out that he’s not a criminal or already married.

A: Time for an intervention with little sis. It just can’t be that the only evidence that she is troubled and unable to make good decisions is this engagement. This is a potentially very dangerous situation. She is leaving her home to drive across the country to have sex with a man she’s never met. Unless she has a substantial bank account he can tap, I’m doubting a marriage is going to ensue. Yes, your sister is an adult, but I’m hoping she has good enough relationships with her family that she will be willing to listen to reason, and even talk this out with a professional. It’s fine for you to check this guy out. But do it quietly and hold the information in reserve until you try to get your sister to reconsider. Even if he’s a registered sex offender, people like your sister tend to believe the accounts from their beloved that it was all a terrible frame-up.

Q. Stalked by Co-worker: I am a 24-year-old female who changed jobs six months ago. Since my first month in the new company, a co-worker has been persistently trying to ask me out. He let me know early on that he has a girlfriend, but things are not going so well between them. I already told him that I like him as a friend but nothing more. We used to hang out a lot earlier, but after this exchange, we have slowly stopped hanging out and talking as much. I recently told him about how addicted I have become to the website Reddit and have been enjoying my conversations there. I have a common username that I use on all social networking sites. Last night, he sent me an email quoting a comment that I made on that website specifically about how I am annoyed by my co-worker’s advances. I don’t know how to deal with this situation. On one hand, I feel stalked and harassed. But on the other hand, I also don’t want to make things any more awkward between us than they already are.

A: First of all, get a new username that hides your identity. Unfortunately, you tipped off this guy to one of your pastimes and presumably your username is close enough to your own that he was able to discern you went online to complain about him. He is not your friend. You need to make explicitly clear to him that you are co-workers and you want to get along in that capacity, but that he has been crossing the line and it has to stop asking you out. Then stop all conversation with him about your personal life. Keep the email he sent and any others and if he continues to harass you, go to HR. Explain you’ve tried to deal with his advances yourself, but this has become a workplace problem that they need to address.

Q. Re: Boys will be boys: My brother is 10 years younger than I am and he practically worshipped his big sister. He used to put on my actual ballet shoes and other various items. He also once stuck a sanitary napkin in his pants. Today he is a macho masculine guy and not one person would ever consider him even remotely effeminate. But he does respect women and knows how to treat them properly.

A: I love the image of a sister-worshipping boy wanting to use a sanitary napkin! I am hearing from a lot of readers whose sons and daughters behaved similarly. Wherever a child ends up on the gender identity scale is fine. But a toddler trying on the clothes of mommy, daddy, sister, and brother is not indicative of anything but loving the big people in his or her life. The father described in the letter needs some serious education on child development and sexual identity.

Q. Transphobic Mother: How do I tell my mom that I’m dating a transgender man? I’m an adult, but I still live with my parents, and she has made some jokes about people that are transgender and has said that they don’t know what they want. I know that it’s within my right to not say anything, but I am very close to my parents, so I hate keeping things from them. She’s met the guy in question, so I can’t just not mention that he wasn’t identified a man at birth. How should I handle this?

A: Since you’re an adult, you start working toward being able to live in your own place so that your social life won’t fall so directly under your parent’s purview. I don’t think you should say anything to your parents at this point. You’re dating someone who identifies as a man and that’s all your mother needs to know. She’s met him and didn’t have any questions about his gender. If you two decide to marry, then yes, this would be something to discuss with your parents, but that sounds as if it’s not now on the agenda. If your mother talking about transgender people is a constant theme, then you should do some educating—and you can make it general for the time being. If she just makes an occasional remark that is not offensive, you can ignore it or address it as the situation demands.

Q. Co-worker Wedding Invite: I am a new teacher and I love my job! I have two wonderful hard-working assistants. However one gets jealous of the other and reverts back to childish behavior (silent treatment) and it will build up for days and explode. This individual also will hear things that weren’t said and blow it up! I literally do not know how to fix it because it’s her own issue. She is wonderful at her job 99 percent of the time. That 1 percent is the only time I dread going to school. I am getting married in the near future and will be inviting one of my assistants but not the other. I want advice on how do I face the backlash when she realizes she is not invited? I know there will be backlash but I rarely do for myself and this one day I want to be peaceful.

A: This is not a question about wedding invitation, it’s about managing an employee with a serious problem. I wonder if you’re teaching math, because I get the feeling your percentages are way off. If your assistant goes cuckoo only 1 percent of the time, that would hardly be noticeable at this point in the school year. But what you describe sounds like a running theme. Yes you’re new and inexperienced, but your assistant’s personality problem is affecting everyone and needs to be dealt with. If you have no idea how to handle this, go to your administrators, describe what goes on, and ask for their input. As for the invitation dilemma, of course you are entitled to invite whomever you like to your wedding. But if you include only one of two people you work closely with every day and who hold the same position, surely you know this exclusion will get out and you’ll just have to deal with the subsequent bad feelings.

Q. Sandwich Generation: My elderly mother-in-law lives in our town in a very nice senior community. Our toddler grandson lives three hours away. My husband and I are old enough to be great-grands (well, at least HE is) but we have only the one young grandbaby. Now that we are retired, we would like to move close to the grandchild so we can be actively involved for as long as we have some energy left. 90-plus-year-old MIL does not want us to move. She thinks we should just drive back and forth to see the baby. This is 1) tiring and 2) does not allow us real involvement. We don’t see MIL that often, even though we are in the same town. My husband does not feel close to her (never has, as she is a pleasant but emotionally chilly person). How awful would it be to move anyhow?

A: I can understand that your mother-in-law wants you around for her last years, but your grandchild will quickly pass through toddlerhood and if you want to be there to help be part of his life now (and the parents of this grandchild are on board with your move) you should do it. This will just mean that the three-hour trek will be to see your mother-in-law. Given your current visiting schedule, it doesn’t sound as if coming every two weeks or so will be that much of a difference. Make a commitment to come on a predictable schedule and call frequently so that all of you are as comfortable as possible with the new arrangements.

Q. Cheating Friend: I just found out that my best friend has been cheating on her husband for the majority of her marriage of a few years. I’ve always known it wasn’t a perfect marriage, but my friend has always painted herself as a victim of her husband’s mistreatment and my support and advice have been based on that perspective. Now that she’s dropped this bomb on me—she’s cheated with multiple people, some emotional affairs, some just physical—I’m kind of at a loss for how to respond. I think I’m the only person she’s told. What is my responsibility here? I still love her as a friend, but I can’t respect her actions. If I come on as too judgmental, I know she will never want to talk about it with me again.

A: You respond honestly but temper the outrage. You say that this gives you a totally different understanding of the dynamics of their marriage, you say surely she knows her inability to be physically or emotionally faithful makes a successful marriage impossible. You tell her you love her but find her actions deeply concerning. If she wants total support and will cut you off because you can’t give it, then the basis of your friendship is as shaky as that of her marriage.

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