Over the past couple of months, my son has been sneaking into my wife and my room and taking her bras and underwear, putting them on and falling asleep like that. He is otherwise a totally normal 8 year old boy. Up until this, he would normally sleep naked, despite numerous attempts to get him to stay in his pajamas. He is normal in school and play. The only major life difference that has occurred is that I have been attending seminary and am out of town two nights a week. It was shortly after I started this schedule that this new behavior appeared. His mother and I are happily married, with respectable jobs even if a meager income. He is close with his grandparents, even though he lives three hours from his paternal grandmother and his maternal grandparents live in South America. I am a bit concerned about this behavior and would like some advice as to how to deal with this in a productive way without making him feel any humiliation or other awkward feelings.
From: Steve, York, PA
Believe it or not, this behavior happens more frequently than you might expect, it's just that parents typically are too freaked to talk/ask about it. At this age, wanting to wear mom's underwear could be because:
1. It's a source of comfort. It's possible he doesn't view them as "girls' clothes" but as "mom's clothes." This particularly makes sense if the changes in your family's lives have been trying.
2. It's an indicator that he might someday identify as gay, bisexual, transgender, or gender nonconforming.
3. It's a fetish (ie, a source of sexual satisfaction).
The fact that he falls asleep in it likely means he is not embarrassed or ashamed (that's good) but that doesn't mean that at some level he isn't wondering why he does this.
Initiate a conversation in a non-judgmental way: "I've noticed that you sometimes take mom's underwear and wear it....." Your goal is to keep shame -- yours or his -- out of the equation so that he will speak freely. Tell him that while not everyone does this, some people do. Ask if he would like to share why he does it, but keep in mind that he may not have a clue. Offer to find a professional he can talk to who will help him understand why he does this.
Here are some resources: gender spectrum.org; PFLAG (Parents, Families and Friends of Lesbians and Gays); "Raising my rainbow," a blog by a mom of a "gender creative" child, especially this post; and a terrific book, "Gender Born, Gender Made," by Diane Ehrensaft.