I'm fairly certain that he's not gay.

October 17, 2005 10:24 PM

I found a bunch of women's clothing in my boyfriend's closet and a bunch of underwear in his drawer. I'm ok with that, I think. How do I tell him?

We've only been togather for a few weeks, and while I like him...

posted by anonymous to Human Relations (35 answers total)

Well, if he's not gay, and he knows how to dress, isn't that what all women want?
posted by zerolives at 10:37 PM on October 17, 2005 [1 favorite]

Ask if you can borrow some outfits sometime. That should break the ice nicely.

I assume, of course, that you know these clothes to be his and not clothes that were left behind by another woman.
posted by qwip at 10:38 PM on October 17, 2005

I realize you can't reply to this ... but tell him what? I discovered you're penchant for women's clothing? How do you tell him that you've been rifling through his drawers?

Seriously though, just mention en passant, "I was looking for a pair of xyz, in your drawers and stumbled upon a couple things, are you saving them for a rainy day?"

There's a good possibility he'll feel violated, defensive, etc. Unless you're worried about finding bodies, why bring this up? Some guys are just lazy.
posted by AllesKlar at 10:39 PM on October 17, 2005

Blast! The cure for cancer is shortly behind my mastery of "your and you're."
posted by AllesKlar at 10:41 PM on October 17, 2005

Just give and use "yaw" -- and turn in the spot a little when you say it.
posted by krisjohn at 10:45 PM on October 17, 2005

If you found it in his drawers and closet, it seems kind of unlikely that he was hiding it.
posted by interrobang at 10:51 PM on October 17, 2005

Probably just some clothes fromthe chick he's banging on the side. Sorry if that's a bit harsh but you say that you've only been dating him a couple of weeks
posted by Botunda at 10:51 PM on October 17, 2005

Approach him obliquly and as non-threateningly as you can. More than anything, make sure he knows that you are OK with it. If you're critical of any thing at all, be critical of something small, like his choice of colors or the size he wears. I think that most guys who cross dress in secret are terrified that somebody will find out. If you are critical or judgmental of him wearing women's clothes, he may never trust you again.

I'm assuming the panties are his. If he's banging somebody else and they are leaving their underwear behind, that's a different show.
posted by faceonmars at 10:56 PM on October 17, 2005

You've only been dating this person for a few weeks? Are you SURE the clothes are his, and not some other girl he was or is currently seeing? If you are, then do not say anything, and continue as if you saw nothing. He'll tell you when he feels ready to (maybe never?) and you'll have to be prepared to act surprised but accepting.

What on earth were you doing rifling through his things, anyway?

Hmm, depending on the situation, it's also possible that he had meant you to see them, and expects you to ask him about them. Follow your gut instinct, I guess.
posted by sid at 11:23 PM on October 17, 2005

He could also just be jerking off on these. One of my brother's dormmates had a penchant for coming on women's clothes, particularly panties, and had quite a wardrobe. Funny what a repressed Muslim background can do to a guy.
posted by klangklangston at 11:25 PM on October 17, 2005

yeah, as opposed to the joys of a repressed Christian (or Jewish, or Hindu) background, I guess

anyway, anonymous: how do you know he wears them? maybe they're another woman's. did you check the size? what about shoes? no size 12 stilettos? then he doesn't wear the stuff, he's simply sleeping with someone else. which gives you an interesting dilemma: would you rather have an unfaithful boyfriend or a cross-dressing one?
posted by matteo at 11:36 PM on October 17, 2005

Currently, my mom keeps clothes in my apartment for when she's in town (in order to avoid having to cart things on the plane). In the past, one of my friends kept part of her wardrobe at my apartment after her new roommates began "borrowing" things from her.

I never hid these clothes, and the fact that he's not hiding the clothes in question -- for whatever reason they're there -- makes it sound like he's never considered them something to be ashamed about.

About how to ask him about it... I wouldn't, at least under present circumstances. The only reason I can think of to have a confrontation would be if you suspected that the clothes belonged to another woman that he was seeing romantically; from your question and tags, it doesn't seem like that's a worry.
posted by aiko at 11:37 PM on October 17, 2005

Rent any Eddie Izzard DVD and watch it together. Laugh a lot.
posted by Rothko at 11:43 PM on October 17, 2005

I have to imagaine that he wanted to "get caught" if he left this stuff in such obvious places, right? And good on you for not going all Republican on him.
posted by JPowers at 11:46 PM on October 17, 2005

I cross-dress. There. I said it. Now...

I've had various success with telling various girlfriends but, from my experience, what I can assure you of is twofold: 1) if he cares for you, he wants you to know, and 2) he's terrified you'll find out and laugh. Or be disgusted. Or react negatively in any way.

You are now in an ideal position to help things go as smoothly as they ever will. You have time to decide exactly how you feel about this - is it something you can accept? Think long and hard about it now, because it's important to him. It doesn't mean he's gay, or that he likes men (though he may). It doesn't mean he wants to be a girl (though he may). It doesn't mean he'll want to swap clothes, or go out together, or make-up together (though, of course, he may). It may not even be sexual (though it most likely is)...

But you can now prepare yourself for...

...the time when he feels confident enough in your relationship to tell you about it. Then you can respond, not react. You won't laugh, you won't run and you won't slap him in the face, because you've had this extra time to think about it. Consider yourself lucky.

But don't blow it now - if you bring it out in the open before he's ready, not only will he resent you for going through his things (however innocent the reason for doing so might have been) but he'll be defensive, embarrassed and angry that you got the drop on him. It won't go well, believe me.

My advice then: think about it all yourself, now, for as long as it takes for you to decide you can handle it. If you can't, get out of the relationship now (and, ideally, without mentioning the dressing). If you can, wait. And when he opens up, be supportive. Don't laugh, don't make light of it (even though you think that might be a "cool" response - it's not); be interested, but not too interested; and listen to him. Telling you will be one of the most terrifying things he's ever done...
posted by benzo8 at 12:29 AM on October 18, 2005 [1 favorite]

I'd say benzo8 has the right of it. I'm impressed by his candor. Quite refreshing, actually.
posted by Goofyy at 12:38 AM on October 18, 2005

benzo's just shown that guys in skirts can have much bigger balls than all of us lame, boring men in suits.
I tip my hat, really.
posted by matteo at 1:09 AM on October 18, 2005

How about the question "Do you want to wear these whilst we shag, or shall I?"

Depends if you're as candid, diplomatic and patient as benzo8's suggestion dictates...
posted by Chunder at 1:28 AM on October 18, 2005

If you're really ok with it, tell him "We need to talk, I found the goods, I'm ok with it, but I'd like you to explain to me." Then have some good sex to reassure him.
posted by mhuckaba at 2:44 AM on October 18, 2005

Hell, I'd say this opens up a world of opportunity you didn't previously know was there - you say you like the guy based on what you knew about him before you found out he was a crossdresser, and now there's this whole additional thing to discover.

If you find you're not particularly enthusiastic about involving yourself in his crossdressing, he's still the guy you liked before you found this out, and this can just be another thing he does in private that doesn't really affect you. On the other hand, if you find you want to explore this with him (and how can you not, really? You've met someone you like who also happens to do something you haven't encountered in an intimate situation before - how many opportunities like this will you get in life?), he's the guy you like with extra opportunities for sexy fun.

benzo8's absolutely right about being patient and letting him tell you, although I'd add that if you're sure you want to let him know you know, make sure you don't give the impression you're laughing at him.
posted by terpsichoria at 4:21 AM on October 18, 2005

Also if you're just sort of crossdressing-curious but want to learn more before you talk to your bf about this, you might want to try reading My Husband Betty [link goes to my review] which is a book by a woman who is married to a crossdressing man. There is also Tri-Ess which has loads and loads of information, links and discussion topics. I know it's a pretty new relationship and I support what benzo8 says, wait and see, and think about it in the meantime
posted by jessamyn at 5:27 AM on October 18, 2005

(Interesting to see who assumes what about the situation. I also assumed the guy's a crossdresser and not a cheater, but it could go either way.)

Ask yourself how well-hidden the clothes were. Does it seem like he wants you to find them? Assuming he is a cross-dresser, he might just be a little too shy to mention it — and leaving clothes out in hopes of getting you to bring it up — or he might be truly and deeply ashamed.

(Hell, the same logic applies if he's cheating. Maybe he wants to be caught — at least subconsciously — or maybe he wants to get away with it. Again, how well-hidden were the clothes?)
posted by nebulawindphone at 6:09 AM on October 18, 2005

Ask yourself how well-hidden the clothes were. Does it seem like he wants you to find them?

What's the origin of the belief that people who don't hide things well are trying to get caught? Freud? Is there ANY basis for believing this is true -- other than the fact that it's a neat bit of pop-psychology which allows us to feel absolved of any guilt we might feel when we read a diary someone left on the coffee table?

I'm sure SOME people fake-hide in order to get caught. Others are probably just sloppy. Or they tend not to snoop so they (wrongly) assume other people won't snoop.

There's a ton of great advice here, but don't assume that your boyfriend wants to be found out. Maybe. Maybe not.
posted by grumblebee at 6:39 AM on October 18, 2005

So to recap he could be:

- sleeping with someone else who constantly leaves her stuff at his place and he doesn't bother hiding them even though you're around and she doesn't bother taking her stuff home (doesn't sound too likely to me if it's several items of clothing and not just a couple)

- keeping the clothes for a friend/relative who sometimes visits and doesn't want to bother to bring her clothes there every time, which would mean she must visit often or not mind having her stuff at someone else's place (ditto)

- keeping the clothes of an ex girlfriend who used to live/stay there, they split and she hasn't bothered to collect her stuff and he hasn't bothered to chuck it out

- keeping the clothes and underwear of ex girlfriends for sentimental/erotic reasons (this and the previous theory are what I'd think of first)

- keeping those clothes because he likes to wear them himself but he hasn't told you yet (most interesting theory, perhaps too interesting to be true?)

So, based on what you already know about him, ask yourself, which of these do you think is more likely? and, which of these would you like to be more likely?

Anyway I wouldn't take for granted that he is into cross-dressing, and I certainly wouldn't bring it up to him as if you've already decided that's what it must be about. The explanation could be a lot more banal than what you're imagining. On the other hand, if he is into that and he hasn't told you yet then he obviously must have his reasons; it may be too soon and he isn't sure how you'd take it. And what benzo8 said of course.

He may also not be too thrilled you looked in his stuff while he wasn't there.

I don't know, you haven't provided any details, but I think it's best to avoid bringing it up at least until you have more familiarity with each other. Meanwhile, enjoy the anticip-p-pation :)
posted by funambulist at 7:42 AM on October 18, 2005

I have to echo the possibility that they may well just be some other girl's or girls' stuff ... like who came home to his house then wore some of his stuff (t-shirts/shorts) when they left to avoid a walk of shame. The last time I moved I collected enough misc girls clothing in my closet and drawers to fill a 30lb trash bag.
posted by fourstar at 7:46 AM on October 18, 2005

Were the clothes in his size? Was the underwear? Not that I'm suggesting anon. go back and check, but if they belong to someone else, that would be one of the easier ways to tell.
posted by S.C. at 8:04 AM on October 18, 2005

You want to ease your way into this conversation with him. Start talking about Dan Savage and his columns. Talk about the crazy stuff you read about in the column and then work your way to some cross dressing letters you've seen Dan address. You are now in a position to get some answers, in a roundabout way of course.
posted by NoMich at 8:21 AM on October 18, 2005

Women's panties commonly come in three sizes and men's hips are usually smaller than women's, so they could easily be in your boyfriend's size. It would be somewhat revealing, though, if the rest of the clothes fit him. Women's shoes are sort of hard to get in sizes above 10, which would be a size 8 in men's shoes.

Or it's possible that he's dating a woman who is six feet tall. It could happen.
posted by faceonmars at 8:55 AM on October 18, 2005

Start talking about Dan Savage and his columns. Talk about the crazy stuff you read about in the column and then work your way to some cross dressing letters you've seen Dan address.

You're assuming the guy is a cross-dresser, which is a shaky and (for the relationship) dangerous assumption. If he's not, he's very likely to be deeply insulted that the assumption was made. I'd say "Hey, I noticed some women's clothes in your closet, what's up with that?" He'll probably answer the question, with some degree of indignation/defensiveness; if he confines himself to going on about his outrage that you looked in his closet (which is not exactly on the level of cracking a safe or even looking into a diary), wait it out, apologize for the invasion of privacy, and then say "So what's up with the women's clothes?" This is probably something you want to clear up, if only because of the worry about potential diseases from potential other women.
posted by languagehat at 9:15 AM on October 18, 2005

You're assuming the guy is a cross-dresser, which is a shaky and (for the relationship) dangerous assumption.

Assumptions don't have to be revealed during this particular conversation, and the author of this question plainly states that cross dressing is suspected. It is one of the tags after all.
Anyway, this conversation could be just about Dan Savage and his freaky letters, but anonymous could then gauge her/his boy's reaction when s/he gets to the cross dressing part. Just pretend that nothing is afoot.
posted by NoMich at 10:39 AM on October 18, 2005

If you go the LH route, I'd emphasize that you don't care if he's cross-dressing, just that you want to make sure he's not sleeping with another chick.
posted by klangklangston at 10:52 AM on October 18, 2005

If he's not, he's very likely to be deeply insulted that the assumption was made.

Huh? Why would he be "deeply insulted"?
posted by sennoma at 2:33 PM on October 18, 2005

Oh please. Yes, we should all accept cross-dressing, homosexuality, and every other variety of the wonderful and various flower garden that is human sexuality without qualms, in fact with a spring in our step and a song in our heart, but if you think that Mister Random Male is likely to be cool with the assumption that he's a cross-dresser, you need to get out of the East Village more.
posted by languagehat at 5:31 PM on October 18, 2005

I also don't think it's a great idea to go look for "clues" in a roundabout way by starting a discussion on the topic of cross-dressing in general. I don't see what kind of reaction other than a "by the way, I like to wear women's clothes too" would be a giveaway. Even supposing he says he is cool with the idea itself, when others do it, and he doesn't consider it some freaky thing, that doesn't mean he is into it himself, and doesn't mean his girlfriend's assumption that he is would go down well.

But again I don't think a bunch of clothes are enough to assume such a thing in the first place. If she really wants to bring it up and thinks he won't mind that much that she was looking in his stuff, then it's better if she just asks flat out whose clothes are those, like languagehat suggests, without jumping to any conclusions.
posted by funambulist at 4:50 AM on October 19, 2005

Man, there's only two ways about it: either: fess up and deal with it up-front with potential consequences (for example, I'd be pissed, sister, that you were going through my stuff. I don't go through my wife's stuff, you know? Really, that's bad form. But what's done is done).

Or else, ignore it. All the "bring it up in a oblique manner" suggestions are bunk. You know what he's going to think if you mention the cross-dressing column in Savage Love? Fuck, she found my girl's clothes. Presuming, again, it isn't all about some ex or something on the side (I bet this whole thread has made you paranoid. And THAT'S what you get for SNOOPING!) If you let it be known that your sexually game, it'll probably come out eventually, though many people have kinks they only wish to use for masturbation too.
posted by nanojath at 12:13 AM on October 24, 2005