Dear Prudence

Dear Prudence Uncensored: The Cross-Dressing Boyfriend

This week, Danny M. Lavery and Grace Lavery discuss a Prudie letter. This week: the cross-dressing boyfriend.

Grace Lavery: I guess there are a few different elements to this story that are worth separating. Though of course the difficulty separating them is part of the problem. First, there’s the question of how you two can get adequate space from each other under social distancing conditions. Second, there’s the question of your response to your partner’s cross-dressing, and his response to you. Third, there’s the question of his having secretly worn your clothes, and your response to that. And then fourth, there’s the abstract question of how to think and talk responsibly about cross-dressing, what it might mean for you and your partner, how it intersects (and doesn’t intersect) with trans experiences, and how to affirm something fragile, without either closing off the possibility of further exploration or assuming that cross-dressing is an incomplete or merely preliminary activity.

Daniel Lavery: That seems to be about the whole of it, yes — my first concern, I think, is about making sure they can establish at least some time apart from one another while sheltering-in-place, even if that “time apart” is artificial, like “I’m going to listen to music in the bedroom with my headphones on for half an hour and pretend it’s my commute.”

Grace Lavery: I agree, I think that’s vital. It can of course be very tricky, and this kind of question intersects in important ways with that of housing security, access to adequate shelter, etc.

Daniel Lavery: right — and part of the problem with having to unexpectedly share very close quarters with a partner due to a crisis is that it can easily blur the lines between “snooping” and “noticing”

it’s really hard to keep anything private if you’re two people sharing one bathroom, one closet, one bedroom, and can’t leave the apartment very often

Grace Lavery: Yes. All of which is to say that I can understand both why the letter-writer thinks she wasn’t snooping, and why the partner thinks she was. Apropos of which, it may be that the partner himself doesn’t feel that he “has to hide” his cross-dressing. The implication that he has an identity in there that he has some responsibility to bring out is contradicted by plenty of testimony from cross-dressers who just want to dress up at home sometimes, and don’t see it as an especially big deal

Which isn’t to say that it couldn’t be an identity he might one day want to share with his partner, or anyone else. Just that I think one probably shouldn’t assume that it is

Daniel Lavery: right — I think part of what’s fueling the tension is this unanswered question of “What are we talking about here? A habit, an identity, a proto-identity?”

hence the beginning that’s like, he’s heterosexual, I’m cisgender

I agree that it’s best to think and talk about his cross-dressing not as a potential stepping-stone to future claims he hasn’t made about himself

So how do you talk about something with a partner like “I think he thinks I think he’s gay”?

or that dance of like — “I’M not ashamed, but I think YOU’RE ashamed”

Grace Lavery: Good question, and I think we have to embark from observing the structural homophobia of the whole scene. (I’m not trying to indict the letter-writer; it really is structural, not personal.) She has found out that her boyfriend has some private relation to femininity that appears at odds with her previous experience of his presentation of heterosexuality. She decides that that femininity is both vulnerable enough to require protecting, indicative of something profoundly true about him, but that that profound truth is not (and could not be) homosexuality. Lastly, she confronts him with having projected a homophobic response onto her, and invites him to do the work of reassuring her that her response is not phobic, but rather affirming. All of this has taken place prior to her real grievance, which is that she feels her own privacy was invaded.

I’m recounting all this in order to ask, how would this narrative look if we didn’t regard bisexual or queer or trans outcomes as challenges, but as exciting prospects to be approached with pleasure and delight?

Daniel Lavery: I mean, I’m certainly sold on that front already

Grace Lavery: Yes but I’m not sure the letter-writer is

Daniel Lavery: So do you think the first step for her is to honestly reassess her own reactions?

Grace Lavery: (For structural reasons, not individual ones)

I mean, sure. I’m not accusing her of malice in that respect (or any others and I think establishing boundaries is the most important action item, but really doing a thorough gut check to try to work out how structural homophobia and transmisogyny might be shaping one’s reactions is a good idea 💡

Daniel Lavery: yes, I do tend to be skeptical of responses run along the lines of “It’s not about [the thing itself], it’s about the way [the thing happened]” – I think it’s difficult, if not impossible, to separate “the thing itself” from “how the thing itself played out in reality”

which is certainly not to say I think it’s the LW’s job to just say “It’s fine, I’m happy that you wore my things without asking, especially after yelling at me”

Grace Lavery: I think it’s really important to separate out the two moments: the first discovery of transvestism, and the second discovery of boundary violation. I think it’s important to work out what are the assumptions and priorities in each case

It is clear, though, that the letter writer is perfectly entitled to draw a hard boundary around clothing-swapping, and I think that, given that her boyfriend hadn’t asked permission in advance, he violated an implied boundary there knowingly

Daniel Lavery: yes, absolutely

and there, I think, it will be important for her to be able to say: What I’m saying is reasonable and appropriate, it’s not judgmental or inherently shaming to say “Don’t wear my clothes without asking”

I got very angry on a letter-writer’s behalf last week whose boyfriend’s mother had been taking her custom-made bras and wearing them without asking

Grace Lavery: Wow, mothers

I was about to say something unkind about mothers but I shall refrain

And yes, that’s true, it isn’t intrinsically cruel to feel affronted on those grounds. Clothing - especially intimate clothing - can be cathected, and it’s reasonable to expect privacy around it

On the other hand, the criticism isn’t *incompatible* with transmisogyny. I can imagine ways in which demands for privacy might mediate or reproduce logics of shame or trans panic

Daniel Lavery: would you mind explaining “cathected”?

Grace Lavery: Subject to cathexis, an investment of libidinal energy in a particular psychic object. Like a child feels about his beloved blanket

Daniel Lavery: like my ratty old flannel I refuse to part with!!!

Grace Lavery: Your “blue friend.” But, I remain shocked about the fate of your former “red friend” - I have never known a cathexis to be displaced from one object onto another with such brutal rapidity. But you are an impressive and unusual person in many respects

Daniel Lavery: [Grace is referring to the other ratty old flannel I previously cherished, then promptly failed to reclaim when I realized I’d left it on a plane and would have to go all the way back to the airport for it. I have no object permanence, baby!!!]

I suppose the best advice I could offer the LW then is to try to make clear two things: One, that he can’t borrow her clothes without asking, that it’s a violation of her privacy. And the other, that she is not out to push or pry or use this as leverage to extract any sort of confession out of him — that he is welcome to talk about this with her if he wants to, but that she’s not going to force him to do anything.

Grace Lavery: That sounds right. I guess I’ve been emphasizing the emotional work the letter-writer can do herself to try to understand the vectors of transmisogyny and homophobia (and biphobia!) that are part of this scene even with everyone acting their best.

But I agree with your plan of action

Daniel Lavery: yes!

and obviously transmisogyny can be at play without the boyfriend in question ever coming out as trans or even understanding himself as having much in common with trans women

but that whole psychodrama of “women’s clothing needs to be hidden and shameful” is a lot of foundation to work against

Grace Lavery: Of course. Transmisogyny, at least in the Serano formulation, has to do with scapegoating of femininity. Trans women are just the scapegoats of all scapegoats - but femininity is the real enemy

Daniel Lavery: and obviously that didn’t originate with the LW, and the boyfriend in question is dealing with it, as you say, structurally

but I do really hope for both of them that they can find ways to think about and discuss this as something beyond just “a shameful secret” that was “discovered”

Grace Lavery: Yes. I really hope it’s clear I’m not trying to pathologize the letter-writer here.

Just calling for attention to the difficulties that both parties are bringing into the room

Daniel Lavery: absolutely! This is the water she’s swimming around in, not a…river she invented