How do I talk to my girlfriend about occasional crossdressing?
March 30, 2014 9:23 AM   Subscribe

I'm a 30-ish heterosexual cis-male in a long-term relationship with an awesome woman. We've been together for about four years, have lived together for about three of those and I think we're both pretty happy with it. I want to talk to her about the fact that I sometimes like to dress in women's clothing and would like to get your opinions on how to approach that conversation. Snowflakey details inside.

Some background: Before I met my girlfriend, I'd sometimes wear women's clothing in private. This was an occasional thing and I had a small collection of clothing I'd wear every now and then. It wasn't a sexual kind of thing, it was just satisfying in some way. After thinking it over, I've come to the conclusion that I like it because it makes me feel pretty and there aren't many other ways to achieve that as a straight man (since straight men aren't 'supposed' to want to feel pretty).

The clothes I like to wear are fairly unremarkable. I'm not trying to play a role - it's just me in a dress. The clothing leans towards the feminine, but I think it's probably the kind of clothing that a woman of my age might wear.

Dressing up like this isn't a core part of my identity, although it's probably a bit more than peripheral. I got rid of my women's clothing when I moved in with my girlfriend. It would probably have been better to talk about it then, but it didn't seem important at the time and my attention was taken up with new relationship limerance, etc. I've thought about it on and off since then and finally got some new clothes, which I've worn a few times when my girlfriend's not around.

I don't want to hide this from her, which seems (and probably is) untrusting and disrespectful, but at the same time I'm aware that this might not be the easiest conversation to have, so I want to approach it carefully. I don't necessarily need for her to be OK with me doing this around her (although that would be great). She's pretty open-minded so I don't think she'd have a problem with the idea of people doing this in general, but I can understand she could have some concerns and worries with it happening in her relationship.

So how do I talk to her about this? Advice from people who have been on either side of the conversation is especially welcome.
posted by anonymous to Human Relations (38 answers total) 8 users marked this as a favorite
Honestly (and I know this is easier said than done), just be frank with her. Tell her that you've been a little shy to share this with her, but that you really trust her and hope she will be comfortable with this part of your identity. Just lay the facts on the table.

If she's as awesome as you say, she will be fine with it. She might be surprised at first, but any good girlfriend would be happy to see you do something that makes you happy.
posted by schroedingersgirl at 9:28 AM on March 30, 2014 [1 favorite]

you've been together FOUR YEARS and she doesn't know yet? maybe she knows and isn't letting on. lots of straight guys do this, it's nothing to be ashamed of. the next time she dresses up really good, just tell her "i wish i could get away with wearing that."
posted by bruce at 9:33 AM on March 30, 2014 [1 favorite]

You've been together for four years. I can see agonizing over this question if you're a few weeks or months into dating, but four years? How does this change your relationship in any meaningful way? Just tell her.
posted by Ndwright at 9:35 AM on March 30, 2014

Since this is just something you do to relax and not a sexual kink requiring her participation (passive or active), I would (as a straight lady) see it on the same continuum as, "I like to take my pants off and hang out in my underwear after work."

But emphasize that you're not asking for a new kind of gender-expression playtime in the bedroom (if that is indeed the case). You're just someone who likes hanging out in the comfort of his own home in a certain kind of clothing.
posted by blue suede stockings at 9:36 AM on March 30, 2014 [2 favorites]

I like to eat a pint of ice cream while crying and listening to Tori Amos from time to time. I only do it when my husband is not home, because it is a solitary pursuit. I don't want to incorporate it into my sex life. I just do it, because it makes me feel good. I only do it alone because I already know he doesn't want to see me all snotty and gross from the heaving cleansing sobs that only Little Earthquakes can shake from me.

If my husband told me what you've said above, my biggest concern would be an unspoken expectation of participation, followed by the fear of the immediate lady-boner-killer possibility of seeing my husband in a dress, which I don't find appealing/attractive. (Sorry, honey. Not my thing. You're still handsome.) If those are concerns for your girlfriend, and you don't think she needs to be concerned about them, head that off at the pass by offering to cross-dress only when she's otherwise occupied and out of the house.

If that's the case, you are really only up for cross-dressing for you, and don't want to bring it in to your relationship as an element other than aiming towards honesty generally, you've got the odds in your favor of this not really being a big deal. If this is a solitary pursuit, tell her that upfront!
posted by juniperesque at 9:44 AM on March 30, 2014 [34 favorites]

Honestly, the way you describe it here makes you come across as thoughtful, sincere and very normal.

I would start by saying that you've been hesitant to bring this up, but you wanted to talk with her about it (don't over-apologize or introduce this as a Deep Dark Secret - it's not that big of a deal and you want to prime her to see it that way). Then just say what you wrote here. I think if you are forthright, willing to answer her questions and talk this through*, and confident about this part of yourself and what this means, everything is going to go well.

*Keep in mind that she may have questions about whether this extends beyond what you're telling her - since you kept this from her for years - so this part of the conversation may be a bit tense. Just assure her of the limited scope of this (i.e. you're not secretly bi, which some women might unfairly jump to upon hearing this) and be transparent after this conversation.

posted by leitmotif at 9:45 AM on March 30, 2014 [8 favorites]

this is not as remarkable or potentially catastrophic as you think it is. tell her the truth just like you told us. FWIW, if i was your GF i would have no problem with this and would probably even be supportive of it. it's just a thing you like to do, without asking for her direct participation; it's really not a big deal. better that you tell her this now than she stumbles upon a small collection of women's clothes and assumes/starts to consider that they belong to another woman.
posted by zdravo at 9:46 AM on March 30, 2014 [2 favorites]

I'd do it like this:

"When I was younger, I used to enjoy occasionally wearing feminine clothing by myself at home. I'd like to experiment with that again. Would you go shopping with me?"

(If you're interested in her participating)

Go somewhere like Ross and no one will even glance at you sideways when you're trying things on. Let her be part of your experience - rather than this being something you were ashamed of or were concealing from her, give her the chance to share it with you and support you. I know she will. I'm another one that would be wholly supportive of this if you were my partner. Congrats!
posted by arnicae at 9:47 AM on March 30, 2014 [1 favorite]

The grains of salt that you should take my advice with are that I am a straight cis woman who does not shave but otherwise is mostly gender conforming these days. (partly because "gender conforming" is a bit more broad for women than for men.)

If I were dating a person I loved, and lived with them, I would absolutely 100% want that person to be happy without harming me or other people, or themselves. That would mean that this person would wear whatever the hell they wanted. I would fight to make a safe space in that persons life for their comfort. If that meant he wants to wear dresses in the house, that's awesome. If that meant he wants to wear dresses out to dinner, that's awesome too.

I'm at a point in my life where I'm feeling the itch to have a baby more and more strongly as every day passes. I'm envisioning the world and the relationship I want that kid to see. A world where one person has to hide who they are for fear of upsetting a partner does not seem like a healthy or fun place.

So, if you were dating me, I would want you to say to me something like, "Hey, bilabial, I'm really comfortable with you, and I want you to know a little more about me. Sometimes I want to try on dresses." My response would be, "Would you like help picking out a dress?"

Now, if you don't know how your girlfriend feels about crossdressing at all you might need an approach that's a few steps back. In that case, maybe find some events where male identified people are dressing up in women's clothes, either for charity or just for whatever. Point it out and just ask her how she feels. I would respond like this, "Oh hey, they are quite a group! That one guy looks kind of uncomfortable. I wonder if it's his underpants or something someone said" In the event that I was looking at pictures of men dressed as women just for laughs, I'd be upset, for two reasons. First, I don't think the way women dress is inherently funny. Second, I really don't think the concept of men dressing as women is funny. Making such things a public spectacle forces men to have to explain why they are doing it, when I don't think it should be up for comment/approval/scrutiny/whatever.

If your girlfriend is appalled at the idea of any man ever dressing in women's clothes, then her acceptance of you doing it may be hard to come by, and I can absolutely see how the information could "damage" the relationship. However, if she really feels that way, then your relationship is already damaged, because you would have to live a very different life, one that involves not even being able to state what your "100%" would look like. She might even say something like "I'm so glad you never do that" or "They must be gay." Those are super huge warning signs.

But difficulty is also possible if she is aware of and in agreement with progressive attitudes toward gender constraints, because many people think they are comfortable with a thing and then in reality find that it takes a lot of work to really embrace it.

And as juniperesque mentions, there are definitely a variety of time and company preferences among crossdressers. Some want to be told that they are really rocking that dress. Some want total privacy. Others want to go catch dinner and a movie in some smoking heels. It helps if you can openly discuss where you fall along that continuum, and be prepared for some compromising.
posted by bilabial at 9:47 AM on March 30, 2014 [6 favorites]

You might find this High Maintenance webisode gives you some perspective or inspiration.
posted by caek at 10:01 AM on March 30, 2014

Try a litmus test: watch Tim Burton's Ed Wood together. Johnny Depp is running around (I mean literally) in pumps and angora sweaters for a good bit of the movie, and cross dressing is talked about in a light hearted manner, though his wife does have some problems with his behaviour.
posted by effluvia at 10:21 AM on March 30, 2014 [4 favorites]

I agree with others who say that you sound thoughtful and caring. If I were your girlfriend, I'd want you to say something like, "When I was in college [or whatever time period it actually was; i.e. before the relationship], I used to occasionally wear dresses to relax when I was by myself at home. It's just something I found comfortable. I've been thinking lately about doing this again, primarily at times when I've got the place to myself. What do you think?"

Rather than asking for her immediate approval or disapproval, you're just asking for her thoughts. I also wouldn't immediately say "But don't worry, it's not sexual!" for the same reasons it's impractical to say to someone "Don't think of an elephant!"—now the elephant is the only thing they can think about. If she asks, you can reassure her that it's not sexual (and that she need not participate), and then you're not the one bringing up the sex angle.
posted by ocherdraco at 10:31 AM on March 30, 2014 [4 favorites]

If you know that she loves you, I would advise that you bring it up like others have suggested. If you don't know how she feels about you (which seems unlikely given that you've lived together for three years) I would probably wait on it.
posted by sockermom at 10:54 AM on March 30, 2014

FWIW I wouldn't try a litmus test like effluvia describes. People might say things in a casual theoretical interaction that would be different from how they'd react to the same situation if it were someone they loved. (Witness e.g. how many conservative politicians' views on gay issues change when their kid comes out.)

I've read a bit on this exact situation, and the research says most wives end up okay with it. You've addressed some of the common worries (is it a sexual thing, is my partner actually gay), so do that when you talk with her. Be aware too that many women in her situation will be less okay the more public the cross-dressing is, and will worry that cross-dressing in private is just the beginning -- that their partner may actually be transsexual, and will later want to live as a woman. To the extent you can speak to those questions, that may alleviate anxiety on her part.

Good luck.
posted by Susan PG at 10:57 AM on March 30, 2014 [9 favorites]

Maybe something like this:

"Hey, can I talk to you about something? Do you think it would be weird if I wore a skirt or a dress around the house? It's not a sexual thing, it's just that they're comfortable and let my man bits air out. How do I know they're comfy? Well, I actually used to wear skirts or dresses back in the day, but I was to embarrassed to let my roommates / siblings / parents know because I was afraid they'd think it's a sex thing. It's not, I just like to wear them sometimes. I got this the other day, would you freak out if I wore it?"

At this point, if she's crying and freaking out, it's probably best to stop the conversation. If she's as awesome as you say, though, she'll probably be saying, "Sure, I don't care. Whatever makes you happy."

I would not care even a little bit if you were my boyfriend and had this conversation with me -- well, I actually would care in that I'd care that you're comfortable and happy. I think that since you know her better than we do, you should try to work into the conversation that it also made you feel pretty -- because my premise is about comfort and that's a teensy bit dishonest based on the motivations you've described in your questions. Maybe one way to do that is to work from black maxi skirts to skirts or dresses that are more feminine and if there's a conversation about it, just say, "It makes me feel pretty," then go back to gaming or reading or making dinner or whatever you were doing.

If she reacts poorly, then still 100% good for you for being true to yourself. There are totally women out there who wouldn't mind this at all.
posted by mibo at 10:58 AM on March 30, 2014 [3 favorites]

I don't think it's necessarily untrusting and disrespectful, I see it as more of a sense of self-preservation kicking in. I have been on the other side of this (except in his case, it was sexual)...please feel free to pm me if you have specific questions you'd like to ask.
posted by kattyann at 10:59 AM on March 30, 2014

I have had a close friend deal with this situation, and he was just honest and upfront about his interest, and his fiance (now wife of many years) was OK with it. I suspect his rather casual attitude (it's this thing that I like, as opposed to it's this Big Deal) made a difference.
posted by GenjiandProust at 11:08 AM on March 30, 2014

I wouldn't see it as untrusting either. Even though it's easier for a man to cross gender boundaries than a woman, this is one of those areas where it's quite understandable for someone to keep quiet out of self-preservation, just like kattyann says.

I would see it as disrespectful but that's because I am particularly open and vocal about liking people who play around with gender like this, and I'd wonder if my partner had been paying any attention to me at all over the years.

It sounds like it would be smart for you to focus the conversation around trust and comfort. I wonder if there are any hobbies or activities she used to engage in that she doesn't anymore because her lifestyle has changed? You might want to think on that and mention it to her - "Hey, remember when you told me you used to [activity]? Ever thought about taking that up again?" That would place the crossdressing in her mind as something equivalent you do just for yourself. As for trust, frame it first. "I've got something really private I want to tell you, and it's because I trust you and love you so much that I really want you to know." This gives her kind of a boost, and puts her in the position to respond with kindness and understanding really easily. Also make sure you don't have this conversation at a time when you would normally then engage in sexual activities. Make it super mundane and the whole "wait is this a sex thing?" part will feel less awkward.
posted by Mizu at 11:15 AM on March 30, 2014 [3 favorites]

One of her questions may be why you kept this from her for four years - I know that would be at the forefront for me and I would take it as untrusting and disrespectful that you had hid it for so many years. So you may want to think about why you didn't and be able to explain that to her. My next thought would be "what ELSE has he not trusted to tell me?" so address that head-on that there are no more secrets. I also think you should bring up the sexual angle rather than wait for her to ask (to me, that is too close to a lie of omission and I would distrust you answer that it was not sexual just because you had avoided the specific sexual topic just as you had avoided telling her you liked to dress in women's clothing and actually purchased some). I am really surprised at how many people say it is not a big thing in their social circles because I know in my circles (where homosexuality is completely accepted and most kinks are ok) there is still a pretty strong reaction against men cross-dressing or straight feminizing their appearance.

I know a few women that are initially accepting of behaviour outside the norm from their partners which rapidly turns into an escalation of behaviour beyond what they are comfortable with accompanied with emotional manipulation: "You said it was ok for for me wear this when you weren't home, why can't I wear it when you are home, oh, i don't feel like taking me dress off, i think I will have sex with you with it on, lets go shopping together - how does this dress look on me?" I think you need to reassure her what the boundaries are and that you will not cross them. If you don't feel you are certain of what your own boundaries may be then find a kink friend therapist and explore your own feelings before you try to work it out-loud with your SO.
posted by saucysault at 11:58 AM on March 30, 2014 [7 favorites]

If I heard a partner say, "it isn't sexual; it just makes me feel pretty"? For me as a straight woman, feeling pretty and feeling like a sexual object for the straight male gaze to appreciate are like two circles on a Venn diagram that mostly overlap. So my reaction would be to think, "my partner is dressing like a sexy lady but he's telling me it isn't sexual and seems to honestly think it isn't sexual, so is he just not in touch with this aspect of his sexuality or what?"

If I heard a partner say, "it isn't a core part of my identity but it isn't exactly peripheral either" or "I don't necessarily need to do this around you (although that would be great)" I would feel confused. I would worry that you're still working out how big a part of personal identity it might be, and how involved in it you'd want me to be, and that it may actually run a lot deeper than what you're currently aware of. I would say be a lot more certain and clear about exactly what it is that you want, and find a way to talk about exactly what you'd ideally like with your girlfriend, not just some crumbs or half-measures that you might feel are all you can hope for.
posted by Bentobox Humperdinck at 12:20 PM on March 30, 2014 [24 favorites]

From an anonymous commenter:
When you tell her it could be good to frame it as "I like to wear dresses" and not "I like to dress like a woman." My long-term boyfriend liked to cross-dress, and the first time he showed me I freaked out even though he'd told me about it beforehand. I'm a jeans-and-T-shirts sort of woman who doesn't wear makeup, and so seeing him in a fussy dress, lots of makeup, pantyhose, and heels made me think that was his idea of what women should dress like.
I've since apologized to him for being self-centered at a vulnerable moment for him, and told him how brave he was. This was in a small town a long time ago. Society has grown a lot since then, and your girlfriend probably won't be as shocked as I was.
posted by restless_nomad at 12:33 PM on March 30, 2014 [5 favorites]

As a wife, I'd want my husband to be happy and fulfilled.

I guess I see a few things to remember in this based on other comments...if you phrase it as asking for permission, you're leaving yourself open to her saying you can't. It's not really her call. Opening up to her and being open to her questions and allowing her to react honestly then to process it slowly are the best ideas. Please don't take initial shock to mean she won't be ok. I tend to prepare people for the worst then they're delighted it's not as serious, or serious at all, as they were expecting. Maybe it's cruel, but I'd not be casual about it at all, I'd be quite formal but loving and open.

To me, the more important take home for you from this, for all readers, and the rest of society is...You are normal; the whole range of gender identity is normal.

Normal is a weird word. We should really talk about common or uncommon, or actually known to us, and not known to us.

Anyway, if you reassure her that your relationship and sex life isn't going to change without her wanting it to, but that you now feel strong enough in your commitment to her to be open about this wonderful thing in your life that makes you feel good...I think you'll be fine. I'd want to be reassured about those things. And I'd be touched that my significant other was feeling safe to. There's no timeline about when this stuff should happen in a relationship. Some people don't feel comfortable getting MARRIED for many years. It's taken you four years to get to this point? I'm cool with that. It means a lot NOW.

Hugs. I know it might seem scary, but it really sounds like you're both going to be ok.

Just for further emphasis though: You are normal; the whole range of gender identity is normal.
posted by taff at 2:31 PM on March 30, 2014 [2 favorites]

You guys like Eddie Izzard? Might be a good icebreaker...

My response as a straight married woman is somewhere along the lines of "eh. I wear pants...". Woman get a lot more leeway than men sometimes. Maybe ease her in with a Utila-kilt?

My biggest concern (outside of sexuality/kink stuff, which doesn't seem to be the case here) would be that you want to look like the guys in Great Britain (ridiculous) rather than Eddie Izzard ("professional transvestite").
posted by jrobin276 at 4:08 PM on March 30, 2014

It has been my experience that unless a woman is rather conservative and old-fashioned, she'll usually be OK with the man in her life being a little glam rock. If you are transgender, things can get more complicated. After all, not every girl is going to be OK with her boyfriend transitioning into her girlfriend, for example. But as a general rule, cool girls like dudes in eyeliner. (Rock stars wear that stuff for a reason!)

If you truly feel like cross-dressing is as far as this will ever go, I'd say tell her that and this probably won't be nearly as big of a thing as you're worried about.

FWIW I wouldn't try a litmus test like effluvia describes. People might say things in a casual theoretical interaction that would be different from how they'd react to the same situation if it were someone they loved.

Seconding this, with qualifications. It is entirely possible that your girlfriend would say harsh stuff about Johnny Depp in a dress (he does look pretty bad in his Ed Wood drag) that wouldn't reflect how she'd feel about the man she loves wearing a dress. On the flipside of that, even if she's a big fan of The Rocky Horror Picture Show and thinks Frank is super hot, that doesn't guarantee she'd be OK with her boyfriend dressing up.

All that being said, it could be useful to start some conversations about pop culture things that feature crossdressing. That way you can get some idea of what she currently feels about male crossdressing, and you can express your appreciation for the movie/band/whatever-it-is and plant the seed in her head that you are at least OK with the idea of men in drag. I'd suggest talking about the stuff where crossdressing is presented as something lighthearted and glamorous (Rocky Horror and Eddie Izzard's standup both being natural topics for discussion!) instead of anything where it's part of a story about transgender people or it's presented as an "issue." You don't want to get into a big discussion about The Crying Game, for example, because that's a story about a cis male/trans woman romance, and brings up issues that aren't really relevant to your situation.
posted by Ursula Hitler at 4:49 PM on March 30, 2014 [1 favorite]

You asked for experiences from either side of the conversation, so I would suggest that the way my platonic straight-identifying male friend told me is ... well, one way of doing so, but maybe not for everyone. He asked me to go for a curry after the pub, proceeded to get even drunker and just blurted it out, sat back and looked at me with a mix of anxiety and relief. He needed some help obtaining items of clothing and footwear and I was pleased to be able to assist him over the next few years with that.

In the context of a more intimate relationship, I think the sorts of questions that might arise after the initial shock wears off could include issues around whether there is a sexual element to this (my friend was very clear that there was, although there was also an element of self-soothing involved) and also whether you'd used anything of hers when the crossdressing happened.

Sending you my best wishes.
posted by Martha My Dear Prudence at 5:17 PM on March 30, 2014

Personally I feel that the "show her X/go to X/etc. and get her to express her feelings about crossdressing" tactic has a sort of facial logic to it but would actually be kind of weird in practice. If someone did that with me, I would be a bit confused, until I started to catch on and then might start to feel like my intelligence was being insulted.

if you phrase it as asking for permission, you're leaving yourself open to her saying you can't. It's not really her call. Opening up to her and being open to her questions and allowing her to react honestly then to process it slowly are the best ideas.

I think this is really great. She doesn't get to decide whether or not it's ok for you to like crossdressing any more than you get to decide whether or not she can be interested in taking up a string instrument, or whatever. It sounds from your description like she's a good person and won't react horribly.
posted by threeants at 7:16 PM on March 30, 2014

Just as an anecdote, this transgendered woman's blog (mostly safe for work, a few underwear photos, the text all seems pretty tame) mentions how she eased into the subject with her wife (casually mentioning buying tights/pantyhose on a foreign business trip "to keep warm," jumping on an opportunity to model things for her "as a joke," and dressing up as a woman for Halloween). You say you're cis-gendered, so it's not really the same thing, and I'm not sure I'd advise the same method (I think bringing it up somewhat directly, especially freely on your own before she accidentally finds your stash and thinks something worse), but some of the trepidation and nervousness may be familiar and maybe you'll find it a helpful read.

You might also get something out of some of the posts on His Black Dress, in which the cis-male author talks about the personal and politics of wearing a dress and feeling pretty.

Oh, and I guess if I were your girlfriend in this conversation, I think the thing I would worry the most about is what this would mean for us, how it would change things. I think the best reassurance would be that this did not mean that you wanted her to change (you're attracted to her, you don't want to leave her for anyone else, you don't want her to become anyone else) and that you don't want to change (assuming this is true: you don't want to become a woman, you wouldn't rather date a man, you don't need her to participate necessarily or do anything different than she has been doing, you still love her and are committed to her). It's understandable that such a long-term secret would be worrying and, depending on her history, may be triggering for this to have been kept quiet for so long, but I don't think this sort of thing is on the same level as other types of secrets may be--you want to tell her, but due to the sensitive nature you just didn't know how yet, and now you want to tell her, because you love and trust her and want her to know about your life, you're opening up to her. You want this to bring you both closer, not drive you farther apart (which may be her worry; reassure her). You're still the same man she fell in love with, and this does not make you a different person. Hopefully, you can get this across as a very loving and trusting step forward in intimacy between you both, not at all a divisive measure of secrecy or shame.

Just throwing thoughts out there. Good luck!
posted by spelunkingplato at 9:49 PM on March 30, 2014

I would just... tell her.

I mean, she's not a bigot about gender stuff, homophobic, anti-feminist, etc, right? And she's a youngish, liberal, freethinking sort of person, right? And you're not asking her to take part in anything sexual that she wouldn't be comfortable with, right?

What do you think is going to happen? It's a tough conversation because you're filling her in on a somewhat important thing that you've been keeping from her for a long time. But I would just preface it with "I need to come clean about something" or "there's something I want to be open about with you that I haven't felt ready to talk about until now", or the like.

Tell her what you told us above. You did a great job of explaining exactly what the deal is.

You may want to also clarify your gender and sexual orientation, if you feel like she could get jumbled up with the idea of cross dressing = gay or women's clothing = identifies as a woman.

I personally don't see what this would change, at all, or what it would even have to do with me, if I were your girlfriend. If my boyfriend told me this, I'd say, "Oh, OK. Yeah, sure, feel free to wear whatever when I'm around" It would not even be a "lady boner killer", for me, though obviously I'm not your girlfriend and YMMV.
posted by Sara C. at 11:23 PM on March 30, 2014

An early boyfriend of mine liked to wear skirts. I think he first told me by saying (remember, we were at most 19) "man you girls are lucky, you get to wear skirts, and they're so comfortable! Nice and airy." I think he went from there to talking about how he was going to wear a kilt, and soon it was just a thing he did. I remember him borrowing a skirt of mine on a backpacking trip. Good luck finding your way into this conversation.
posted by slidell at 11:39 PM on March 30, 2014

I dated a guy who cross-dressed. He was white as a sheet and shaking when he told me. I was just like, oh, cool, like dresses or full evening gowns? I really didn't care. I love wearing traditional mens clothing and if I lived 200 years ago I'd have been thrown in jail for wearing pants, so I completely get it. He was from a very conservative culture, and ironically did not support me dressing more masculine...

Sexism sucks and gender politics are a minefield of insanity, good luck with this conversation!
posted by Dynex at 9:56 AM on March 31, 2014

I agree with others that being upfront and honest is probably the way to go. But I think your biggest hurdle might be reassuring your girlfriend that crossdressing for you isn't sexual and is not indicative of a sudden (or hidden) desire for men. It will be very easy for her to arrive at those conclusions, simply because they are so closely associated with crossdressing.

That said, definitely share with your girlfriend how dressing up makes you feel! You want to look/feel pretty/attractive and there's not a damn thing wrong with that. Who cares if you're a guy? It's a ridiculous double-standard to say that a man shouldn't want to feel pretty/desirable. So I say rock it. You're not asking her to participate or even be present, so if she has her reservations or isn't on-board, don't let it get you down - it may just have to remain your thing you do in private - and there's nothing wrong with that either.
posted by stubbehtail at 2:37 PM on March 31, 2014

First, I want to say that it's very awesome that you want to be authentic with your partner about something that can be very difficult to talk about and share.

But before we get to the question of how to broach the subject with her, I would like to know: why would you settle for a partner, or a relationship, where you cannot be authentic about something like cross dressing? Even if it isn't a core part of your identity, it still nonetheless seems rather important to you. You can certainly have a partner and a relationship with a woman who would not only be excepting of this but would also be supportive and excited about it – Dare I say it, she might even be turned on by the prospect. But it's impossible to meet a woman like this or have a relationship in which your cross-dressing is not only acknowledged but also celebrated, without first being upfront about it .. If not immediately, then at least in the beginning stages (eg perhaps 3-6 months in ..

I think you need to prepare yourself for the possibility that she won't be cool with it -- either because she doesn't like the idea of cross-dressing, or because she doesn't like the idea of being in a relationship with the man who hid this about himself for four years.

Either way, regardless of how she reacts, know and understand that you deserve to be completely yourself, and can absolutely find a partner who is comfortable with you looking pretty/fierce ..

Now: about your question .. How to tell her? Maybe over wine and a home cooked meal. Let her know you have something important to share that you haven't felt comfortable discussing before. Be honest about how private it is and how vulnerable/afraid you feel .. But also present it as something really great and fun about you that you want her to know about..

Don't present it as A Bad Thing. It's a cool thing about you that you've had a hard time talking about with others .. Then just tell her. And maybe let her know that you are happy to answer any questions she has. Don't try to anticipate what her concerns will be. Just see how she responds And trust yourself to respond in the moment.
posted by Gray Skies at 7:13 PM on March 31, 2014

[This is a followup from the asker.]
First, thanks for all your advice and suggestions. They really helped me think through how I feel, and how best to express that and what kind of questions might come up. We had the conversation a couple of nights ago and it went really badly. Not really because of what I was saying, but because it triggered a conversation about some of the deeper issues in our relationship. I ended up feeling pretty hurt by her reaction, which was essentially to frame the cross-dressing as the latest in a series of ways in which I've forced her to make compromises and left me feeling like I was just a collection of shit she has to put up with. (Like any relationship there's some compromises on both sides).

Even in my worst case scenario I thought this would be taken as one (possibly negative) aspect of someone she loves. I thought I could count on some level of respect and understanding (or at least the desire for understanding), but there was just this feeling that I wasn't living up to some imaginary standard of good-boyfriendness and all the good aspects of our relationship didn't matter. But I deserve to be with someone who acts like they actually want me to be happy and who won't default to seeing anything I do that isn't some undefined version of perfect in the worst possible light.

Like I say, I was feeling very hurt by the whole thing. So we had another conversation, which went a lot better. I told her the above, she apologized and we talked more about the underlying issues that made things go so badly the first time round and in general what we want from the relationship. It's been a really hard few days for us both, but It's very clear that we needed that conversation much more than deciding if she's OK seeing me in a dress (not yet, but probably after she's had time to get used to the idea and we've both recovered a bit from the emotional turmoil of the last couple of days)
posted by cortex (staff) at 2:49 PM on April 1, 2014

I am so sorry that the conversation was so difficult. It sounds like you're processing it as well as you can. I don't have much to add except that I hope this turns out to be a truly positive turning point for you. I just wanted to send some good vibes your way and maybe offer a tiny bit of virtual comfort.
posted by JanewayJunior at 4:51 PM on April 1, 2014 [1 favorite]

I am really impressed that you had this conversation and that you did this. I want to send you a hug of support and a big kudos. And you are so right when you say that you deserve to be with someone who wants you to be happy. It took me a long time to get to that same point (one that is obvious to a lot of people I guess but wasn't to me) and I just wanted to day that your attitude is very good and healthy.

I hope this turns out well and strengthens your relationship. If it does not, I trust that you know that it's not because you brought this up. I don't want you to be afraid of talking about this in the future if you ever have other partners.

Good luck, and from one totally insecure, boundary-challenged, frightened-to-discuss-anything-serious-with-her-partner stranger on the Internet, nice work. I wish I could do half as good a job as it sounds like you did in this situation.

Take care of yourself.
posted by sockermom at 5:37 PM on April 1, 2014 [1 favorite]

Wow, I'm so sorry it went poorly. But I really like what you're saying about what you deserve. If there were ever a good catalyst to sort out underlying relationship issues, this is it, I suppose. It's OK to shift the focus to what else is going on instead of the dressing up thing, because your comfort and happiness isn't really something anyone should make into a "compromise." Compromises are for picking out drapes, visiting annoying parents and picking shit on Netflix. This is more like you complaining that you always have to "compromise" some value of yours when she wants to wear yoga pants around the house to relax, when that really doesn't cost you anything and makes her happy. But anyway, I'm very proud of you for whatever that's worth and good good good luck to you.
posted by mibo at 7:17 PM on April 1, 2014 [1 favorite]

Hello - I am so sorry I am coming to the conversation late, and I hope you are still reading. Perhaps it is too late to give advice but maybe other readers will find my experience useful.

My first boyfriend (I met him in my early 20s) really enjoyed wearing female lingerie but I doubt anyone would have ever expected this as he was such a macho sort of fellow. In fact, I was attracted to him because he was so tough and streetwise. I think if he had spoken to me about it bluntly, being naive about relationships as I was at this time, and being attracted to ultra masculine men, I would have become fearful. It may be the same sort of thing if you are in a relationship with a person who is insecure, unsure, or questioning themselves. In my case, I would have assumed he did not want to be in a relationship with me so much as want to be like me. I also would have questioned my femaleness, if I was attracting "feminine" men. I would be worried he was just with me to gain information on how to dress, do hair, do makeup - something many men would never learn how to do without a "mentor". I am very grateful I have moved past this prejudiced mindset, but that said there are still many perfectly nice and wonderful people who have these ideas. The gist of this is that speaking bluntly to someone might trigger fears they did not even realize were within them.

Now, I actually enjoyed having the first boyfriend dress in my lingerie because he approached it in such a fun and non threatening way. After a romantic interlude, he tried on my discarded lingerie as a "joke" and I laughed a great deal since I found it funny. Since it was presented to me in a non threatening way, when he did it a second time I sort of got the drift (that he liked it but it was all for fun) and encouraged him more. I think my point is to present it as something fun and silly to do and go from there. I know for you it is not a silly thing, but I am writing this keeping in mind you are trying to bridge a communication gap with your partner. If the partner reacts negatively to your "joke" you know they are not compatible in that way and can stop doing it out of respect, but if they laugh and encourage perhaps you can escalate in a respectful way.

I am no longer with that first boyfriend but I realize now I am very open to these things and sometimes find myself picking up on subtle cues from others to try this, with good results. I have noticed some macho men who would balk at female clothing love having their hair or makeup done for instance, and they will inevitably drop this as a silly drunk idea. Perhaps if you have a partner who feels uncomfortable with the female clothes you can see how she feels about makeup or hair styles (presuming you hair is long enough)?

This is not a kink of mine, but the story just goes to show that you never know someone's interests until you subtly introduce something as a "joke". I know for many this would seem untruthful but it worked on me and as a result I am much more open to seeing jokes as a way to introduce secret hopes.
posted by partly squamous and partly rugose at 10:06 AM on April 5, 2014

Congrats on having a very difficult conversation! I know how terrible it can feel when something like this goes "badly", but I want to encourage you .. as you seem to already know, you two really needed this conversation. Whether you stay together or part ways, being authentic with each other is never a bad thing. You are growing through this - individually and together. Not to minimize the importance of this relationship, but it almost doesn't matter whether you stay together or not, whether she accepts the cross dressing or not, whether you're compatible or not.. what matters is that you both get really clear about your emotional needs and capacities, and that you get in touch with your truth and commit to honoring it, regardless of where it takes you.
posted by Gray Skies at 4:10 PM on April 5, 2014

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