Dear Prudence

All I Want for Christmas

Prudie’s advice on a boy who begged Santa for a skirt, a boorish brother-in-law who ruins holidays, and a gift-giver who’s had a change of heart.

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There will be no live chat at on Monday, Dec. 27. Prudie will resume Monday chats on Jan. 3 at 1 p.m.

Dear Prudence:
I am the father of a bright, artistic, and thoughtful 5-year-old boy. He enjoys playing dress-up and, from time to time, putting on his mother’s shoes or jewelry and declaring that he is a girl. Recently, when my wife and I asked him what he wanted for Christmas, he told us he wanted a skirt so that he could be a girl. We weren’t sure whether he was serious, but when he saw Santa at the mall, he very earnestly declared that he wanted a skirt. Since that time, he has written several letters to Santa, and in each he has asked for a skirt. (As an aside, we gladly let him dress up as the Wicked Witch of the West for Halloween, which provoked some stares and insensitive comments, to which he was thankfully oblivious.) While we want him to be his own person and be comfortable in his own shoes (ruby or otherwise), my wife and I aren’t sure whether to honor this request, as he undoubtedly will want to wear the skirt outside of the home eventually, which leads to a series of difficult conversations that we aren’t prepared to have with a kindergartener. Yet we know he will be heartbroken if Santa does not bring him a skirt of his own.

—Conflicted at Christmas

Dear Conflicted,
How lucky that your son has parents such as you, who will adore him, ruby slippers and all. It’s too early to know for sure where his desire to dress up will lead. But studies show that little boys with a persistent interest in wearing girls’ clothes, and who have other nonconforming gender behaviors, have a strong likelihood of eventually identifying themselves as gay. If that is the case for your son, when the time comes for him to come out, happily for your relationship with him, it will come as no surprise. My colleague Hanna Rosin’s fascinating piece about these children makes the important point that the vast majority are not transsexual. To the concrete-thinking mind of a 5-year-old boy who likes typically girly things, saying he’s a girl is a way to express this interest. I spoke with Catherine Tuerk, co-founder of the Gender and Sexuality Development Program at the Children’s National Medical Center. She said it’s very important that you have a talk with your son because you’ve got reassuring news to tell him: that although he may suspect he’s the only boy who feels the way he does, actually there are a lot of boys like him, and as he gets older, he will make friends with many of them. Explain to him that there are different kinds of boys—he’s a boy who’s interested in things girls also like, and that’s terrific. You can tell him some boys act more like bumblebees, some like butterflies.

When he opens his present, he will see that Santa heard his plea and delivered a skirt. But Tuerk said you need to have another conversation, one that’s going to be a little harder, about the skirt. You have to explain to him that not everybody understands how many different kinds of boys there are, and so if he wears his skirt to the playground, or to school, there are going to be people who say mean things or make fun of him. Tell him you want to figure out the places he can wear his skirt—at home, maybe grandma’s, etc.—where he can enjoy it and feel comfortable. This conversation is not about conveying shame, but about giving your child good options, and not locking him into a limited identity (“The boy who dresses like a girl!”) with his classmates. As Tuerk points out, often as these boys get a little older the intense desire to dress up wanes, and they find other avenues—art classes, theater—to express their interest in beauty and fabulousness. There are many conversations ahead for all of you, and at the CNMC Web site are materials on childhood gender issues, book suggestions for you and your son, and information about support groups. Talking about your bright, thoughtful, artistic son with other parents of similar children will benefit you and your darling butterfly.


Dear Prudence: Holiday Ingrate

Dear Prudie,
My husband’s sister recently got married, and none of us can stand her husband, “Blake.” He is an arrogant, rude know-it-all who has never said one pleasant thing to anyone in the family since we met him. It’s all about how much more he knows about everything than the rest of us. We now dread family functions if Blake is going to be there. I’m afraid someone in the family is going to break and either chew him out or punch him. I’m also afraid that it’s only a matter of time until he starts treating his wife like the rest of us. Is it appropriate for someone to have a private talk with Blake or my sister-in-law about his treatment of us? My sister-in-law is the sweetest person, and I don’t want to tell her how much we hate her husband. Should we just grin and bear him for her sake?

—I Don’t Know Enough

Dear Don’t,
Since Blake knows everything, I wish he could enlighten all of you as to why a sweet person from a nice family would marry such an overbearing loud-mouth. It is amazing how one person can hijack an entire group’s good times, but all of you can’t let blow-hard Blake ruin your family gatherings. It probably won’t be too productive, but it’s worth it in advance of Christmas dinner for someone to pull your sister-in-law aside and say that sometimes Blake gets argumentative at family gatherings, and you would all appreciate if she could ask him to tone it down. But the rest of you can’t let Mr. Supercilious ruin your holiday. Everyone should have some stock phrases ready: “Please let me speak, Blake.” “Blake, this is becoming a filibuster.” “You certainly are well-informed.” Perhaps there’s an older relative with some patriarchal or matriarchal chops who can address Blake. Someone with authority who’s willing to say, “Blake, you’ve been dominating the conversation. Please take a break and let someone else speak.”


Dear Prudence,
I recently broke up with my boyfriend of several years due to his infidelity. I’ve attended numerous events and holidays with his family, whom I have grown to love, and am friends with many of them on Facebook. I want to somehow communicate with his family that I care for them and am sad that I won’t be seeing them anymore. I’d also like them to know that our breakup is not because of something I did, as I doubt my boyfriend will give them the real reason. Is there a respectful, classy way to say goodbye to his family? Or should I just quietly disappear?

—Broken Up

Dear Broken,
How ideal for you that the Christmas card was invented. Sending them will give you the opportunity to express your good wishes and wistful regret that you’ll no longer be at family functions. The card is not the forum—actually, there is none—for you to express your hope that they are able to enjoy their Christmas despite the horrible fate of being related to such a lying ratfink as your ex. Instead, you include a note in the card that is personal while also being neutral enough to be displayed on the mantelpiece. Just say how much you’ve enjoyed their hospitality over the years, that you think of them fondly, and you hope they have a wonderful new year. Restrain yourself from adding, “And please warn the next woman he brings around to get checked regularly for STDs.”


Dear Prudie,
A friendship of several years has inexplicably run its course. Nothing happened—she just got “too busy” and quit calling me or returning my calls, and now we haven’t spoken in many months. I have accepted this but am now wondering about a gift I gave her for Christmas a few years ago. It was handmade, took me a long time to craft, and was expensively framed. I have never asked for a gift back, but in this case, I strongly suspect it’s in a box in her basement, as she has recently moved. If she values it, then I absolutely want her to keep it. But would I be wrong to ask for it back if it is in said basement box and is likely to remain there for eternity?

—Want It Back

Dear Want,
Inexplicably ended friendships are always painful, but you don’t want to compound the hurt by finding out that your lovingly hand-stitched rendering of a mongoose has been turned into a dust rag. A gift to a friend should be freely given with the hope that the recipient enjoys it. The recipient’s responsibility is to express proper appreciation. (In ongoing gift exchanges with those you are close to, if you notice your gifts are never displayed, used, or worn, then maybe it’s time to put a halt to the gift-giving.) Accept that your friend has dumped you and possibly dumped your gift, too. Don’t let that sour you on making beautiful things for people. Simply accept that once it’s given, it’s gone.


More Dear Prudence Columns

A Cornucopia of Crises: Prudie takes on Thanksgiving quandaries involving uninvited guests, the ghosts of holidays past, and exiled smokers.” Posted Nov. 18, 2010.

Bob & Carol & Ted & Malice: My parents’ swinger friends are trying to blackmail our family after Mom and Dad’s tragic deaths.” Posted Sept. 30, 2010.

No Debt of Gratitude: I borrowed cash from Dad to care for my dying mom. Now he’s demanding payback.” Posted Aug. 12, 2010.

Dirty Pretty Things: My girlfriend has worn the same undergarment for weeks. Isn’t that disgusting?” Posted Aug. 27, 2009.

More Dear Prudence Chat Transcripts

The Grinch Who Stole Thanksgiving: Prudie counsels readers on Turkey Day predicaments, such as flying solo for the holiday, hosting irritating in-laws, and attending multiple dinners. Posted Nov. 22, 2010.

Baby Mama Drama: Prudie counsels a sleuth who uncovered a baby-trap scheme—and other advice-seekers.” Posted Nov. 1, 2010.

The Family That Bathes Together: Prudie counsels a mother who wonders when the time is right to stop bathing with her little boy.” Posted Oct. 12, 2010.

Help! I’m Too Hot for My Age: Prudie counsels a woman whose youthful looks bring her nothing but problems—and other advice seekers.” Posted Feb. 8, 2010.

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