"Listen, you and I are going to play a game called 'Guess What I Just Swallowed.' Go."
But most terrifying of all is that at one point or another, parents eventually have to let the child go. They have to back out of its bedroom while it cries, close the door and let it learn to deal with darkness on its own. There are just some lessons parents can't teach. Of course allowing kids to learn through trial and error means a few of them will break bones climbing trees and others will get Legos lodged in their ears and still others will go a completely different route by deciding it might be fun to cross-dress for a summer, like I did, when I was five.
In an effort to understand how parents find the right balance between helping and staying hands-off, I recently spoke with my mom and dad about the month period in my childhood when I thought I might like wearing a dress. While I remember both of them being supportive at the time, as an adult I wanted to know what they genuinely thought about my decision. I can't say for certain that that point in my life taught me anything except maybe a healthy surrender to embarrassment, but I was far more curious to find out what my parents learned, or thought they were learning about me. Below is the full and completely real interview I conducted.
Me: So right off the bat, do you remember the time in my life when I experimented with dressing as a girl?
Mom: Well yeah. Of course I remember. Which time?
Me: There was more than one?
Mom: There was the time your grandmother and I made you up like a prostitute for Halloween and there was the time you wanted to have a dress to wear so I bought you one.
Me: The second one.
Mom: Oh. OK then. You know, your grandmother and I really bonded over that prostitute thing.
Me: We'll talk about it if we have time. So you remember when I owned and wore a dress?
Mom: Of course I do. You were darling in it. I still have have it, just a second.
Dad: Not really, I kind of remember. [Pause] Hold on, Mom is showing it to me right now. It's kind of pink with some flowers on it. It's a very nice dress.
I can't even claim to have done the damage in the lower left. Even time was tougher than I was.
Me: Do you remember why I showed an interest in wearing it?
Mom: Yes, you were about 5 and we were staying in the house on Cape Cod. Your cousins dressed you up in a dress and you kind of liked it or at least you thought it was OK. Mostly your cousins were showing you a lot attention which, of course, was something you loved. It was that summer you insisted on being called Pickle. I don't know why you did that. That was weirder than the dress thing.
Dad: No, I don't remember. And you didn't show an interest in it for very long. Why are you doing an interview about this?
Me: I'm doing it for my column. I thought it would be funny.
Dad: Oh. Alright. I guess we'll see.
Me: Do you remember when I asked you to buy me one?
Dad: No. I think it was the kind of thing that just happened.
Mom: I do. After we got home from the Cape you asked for one and I said, "Sure, that would be great." And I got you a calico dress with smocking on the front and a white collar.
Me: Really? That sounds fairly conservative. I didn't want anything more low cut than that?
Honestly, this feels more my speed.
Mom: No, you were just happy to have a dress. You didn't care about the style, that wasn't important to you.
Me: What was your thought process when I asked for it?
Dad: You know, kids that age do all kinds of crazy stuff and you just have to go, "Oh yeah, well ..."
Mom: I thought it was interesting and that it was kind of nice that you were exploring all these things without being afraid of them.
Me: Would you say you were proud?
"Honey, mommy just needs a minute, OK?"
Mom: I don't think I'd use that word. I was curious about it and happy to support you. There wasn't too much you didn't get to experience that you were interested in.
Me: How many ti-
Mom: It's not like you could do anything you wanted, you weren't running around without rules. But you were allowed to try things that were harmless and there was nothing harmful about a kid wanting to try something like wearing a dress unless adults made it harmful.
Me: How many times did I wear it?
Dad: I don't know, but not very many.
Mom: You wore it a few times. You and your brother would get buzz cuts in the summer so it was funny to see you with a shaved head wearing a dress. You also had a summer later on where you wore bracelets that went all the way up your arm.
Me: Friendship bracelets?
Mom: No, I don't think so. I don't think anyone gave those to you. You went out and got them.
There's a very good chance some of them contained puka shells.
Me: OK, let's stick to one emasculating piece of my childhood at a time.
Me: Did I seem to be enjoying myself when I wore the dress?
Mom: Yeah, you liked wearing it the first couple times and then you didn't wear it anymore.
Dad: I remember you wearing it once. You seemed to be having a good time, I guess.
Me: Did I ever wear it out in public?
Mom: I think so, or maybe I just mentioned it to other people. I can't remember. I just remember people saying, "You bought him a dress? Why would you do that?" And I said, "He wanted one." I didn't particularly care what other people thought. I knew it was okay to let you try things like that.
Dad: Maybe once but we didn't go out to dinner or anything. Later on my mom dressed you up like a hooker for Halloween. Then you went out. You were a good looking hooker.
Me, c. October of 1991
Me: Thanks. Do you remember why I stopped wearing the dress?
Mom: It lost its novelty. You also didn't have your cousins there and it wasn't like all the other kids you knew were going to start wearing dresses. Although, who knows what they would have done. It really was a cute dress I picked out.
Dad: I have no idea. I have no idea why you ever started, but I know it didn't last very long.
Me: Did you ever secretly hope that I would have been born a girl?
Dad: Of course not.
Mom: Sure! I don't know if I would call that a secret. I wanted a girl. Sorry. This whole thing was a great opportunity to buy a dress for someone. I was pretty excited because I was missing out on that. I was more amenable to it maybe than someone who wasn't missing those chances.
I can't imagine why.
Me: Anything else you want to add?
Dad: If you're looking for embarrassing stories, why don't you interview us about the time you used to go out at night as a superhero? I bet everyone would like to hear about that.
Mom: You should do an interview about the time we dressed you up as a prostitute.
Dad: You were too old to be doing that superhero thing. I don't remember you stopping a single crime either. You were pretty bad.
Me: Thanks. Maybe next time.