lunge across the table, grab his wig, and run around the restaurant screaming "I've got yo' hat, bitch!" Then you won't be so embarassed just sitting down with him. If you don't like him the way he is, leave it alone. I wouldn't want you as a friend if you tried to change me.

There is no way of handling this situation tactfully. You have to accept him as he wants to present himself to the public or NOT hang out with him publically. You can talk to him and tell him it makes you uncomfortable, but I'm sure he'll probaly say it makes him uncomfortable to deny how he wants to live. Personally, I'd not go out in public with him. You say he's a good friend for 30 years, if thats on the line and you prefer to be wo his freindship then tell him you don't want to be around him and his cross dressing ways. Is this new? When did he start cross dressing in public? That would freak me out too if a friend pulled that recently. If he's always done that in public, then its no surprise, right?

So what exactly is it that makes you uncomfortable? Is it him crossdressing, or is it the reactions of other people? That's two different things. If you are uncomfortable by your friends crossdressing, because this is new to you, then it's something you have to get used to. I think it's quite normal to feel a bit strange about it in the beginning. Just talk about this with him, not in the way that you want your friend to change, but to change your own feelings about this. Try to get some understanding of why this is what he wants to do. You might also for example check out some movies about the subject, to give you more insight in the subject. Why does he do this? There are many reasons why people crossdress. He might be transsexual, or pure crossdressing for other reasons. An other reason why you might feel uncomfortable about this is because of other people's reactions. And to me, that's quite logical too. It's very brave of your friend to do this, and it takes bravery from your side also. Some people might be okay with it, but there wil be many reactions otherwise. People might laugh at him or much worse, some people might get violent. You seem like a good friend to me. Your question is in my opinion an honest question. I think the answer is not in you changing your friend, this is a big thing your friend is doing and he needs all the support a friend can give. He is very couragious in doing what he does. (I'm constantly referring to 'him' as 'him', I'm not sure how 'he' wants to be seen, it might be as 'her') That you feel uncomfortable at this, especially in the beginning, is pretty logical. Just talk to him about this, not for the reason to change him but for the reason to get more comfortable about this. Some movies that I found very touching: - Head On - Hedwig and the Angry Inch Good luck to both of you and take care!

Thank you BloedEnMelk for your kind and understanding words. I wouldn't try and change my friend for any thing. He is funny and compassionate, a great human being. We've been friends for a long time. I like his personality just the way he is. I'm uncomfortable with the way people stare and laugh when they see him dressed in 4" high heels, tight mini skirts, the sparkling tiara that he wears on top of his blonde wig and the heavy foundation makeup, eye makeup and bright red lipstick. People stare at him when we are out in public. It's uncomfortable for me that so many people look at us when we are together having lunch or shopping. I never said that I wanted to change him, I said that I'm uncomfortable with all of the looks people give him, they actually stop and stare. I was looking for some kind of answer that would make me feel more comfortable with the looks people give him when we are together. I never said that I wanted to change him.

There's not much of anyhing tactful to be done about it. Either you come to terms with the fact that he generates stares and attention, or you don't. Unless he can tone it down to the point of being passable, and wants to do that if it's possible, he's just going to draw attention. You might be able to point out that you love him dearly, and you enjoy his company, and you don't want to change who he is for anything, but you would appreciate if he would make an effort to tone it down just a notch (maybe ditch the tiara, for example) when you're out together. Now, I'm totally biased on this point, but the fact that he's generating attention isn't in and of itself a bad thing, and given that everyone can see that I'm a man in a skirt and heels when I'm out dressed. Part of the fun is attracting attention, so you may just have to come to some level of acceptance with the attention he's going to get. If he's fine with it, then there's certainly no need to be embarrassed for him. Only you can decide if you will continue to be embarrassed or uncomfortable for you.

Buying him a more realistic wig or paying for a cosmetic makeover for his birthday are possibilities if you think he might like to pass better as a woman. If he doesn't seem to care, then maybe you'll just have to veto going certain places with him if you feel the embarrassment is simply too much. Another answerer here suggests that you are not much of a friend if you try to change him. That may be, but it might be instructive for both of you to see how he reacts to your occasional refusal to go out with him. -- Just how good of a friend is he if he ignores your obvious discomfort?

if you are embarassed, do what most friends would do, you said you go out shopping right? figure out her (yes, i said her because even when crossdressers are dressed they also want to be seen as beautiful women just like u n i even tho that may never happen)sizes and help her pick out clothes and shoes and make-up you'll think she'll look good in. once you do that or help her realize she needs a wardrobe makeover, trust me she'll love you for it. have her watch Stacy London and Clinton Kelly's What Not to Wear on TLC, it's a great fashion show!!! this is what a true friend would do!!! :>)

Tell him how you feel. if he/she is a good friend they will understand your feelings and try to find a way to make things work so ya'll can do what you like to do without being werided out!

Make up + crossdressing? how to start? I want to try cross dressing? i need help i want to try cross dressing i might want to take it slow or fast idk what makeup should i wear what clothes should i wear what other stuff should i do i want to go all out and look like a women my wife is a way for a 19 months and she is ok with me doing this but she cant help me. i am going to buy my own stuff. it can be expensive. I have lots of money to spend to do this. what if i like it then should i to it full time we dont care what other people think. if we go out into public when i look like a girl we will act like friends what if i like to cross dress please help