I find it interesting to think about who finds crossdressing funny and in which contexts. There are a lot of plays, movies, books, and television shows where crossdressing comes up and often it is supposed to be comical. And much of the time when crossdressing comes up when kids are playing, or at Halloween parties, or youtube videos of guys being talked into crossdressing by girls, it is supposed to be funny in these cases. And people do laugh. In fact, I know many strong Christians who have these types of movies as their favorite movies because they find it so funny.

This is a hard thing to figure out for me, because I have never found crossdressing funny, but only pleasurable and sexual, or disgusting. Movies like Mrs. Doubtfire, Tootsie, or Sorority Boys are supposed to funny, but some movies like that have fueled my sexual fantasies, and others have disgusted me more than most things in the world do. It’s strange that it is usually one or the other for me. (Similarly, pictures of men crossdressed online are enjoyable to look at if they are convincing, but they disgust me immensely if they look like a man in a dress). So I really have great bias, but here are my thoughts.

I admit that a lot of people probably find crossdressing funny just because it is something that blurs normal boundaries and looks silly. For example a lot of people also find animals wearing clothing to be funny. But I’m wondering if crossdressing is most funny in cultures in which there are still rigid gender stereotypes about what men and women are usually like. Or more specifically, maybe crossdressing is most funny to people who believe in and operate under rigid gender stereotypes. The more a culture or person goes in the direction of allowing people to be fully human in their personality, emotions, and jobs, the less crossdressing is funny. And I think those who don’t find crossdressing funny because they are against rigid gender stereotypes, maybe they view crossdressing intended for comedy to be degrading and disgusting and offensive. (In other posts I write about how I think the more a culture has these rigid gender stereotypes, the more that culture will nurture people growing up with gender dysphoria and struggling with crossdressing).

I have seen, lived in, and studied some very traditional Christian communities, where men are supposed to be a certain way, and women a certain way, and gender roles from Scripture have taken on an unbiblical extreme. I have fought hard to bring people back to the Bible’s real view of men and women, and get rid of the bad gender stereotypes. But in these traditional Christian communities, men can’t be fully human, and women are seen as inferior and aren’t allowed to do certain things. In these cultures, crossdressing is seen as hilarious. But in the other communities I’ve been in like my college, where people are more educated, and they have thought about gender issues, and are against the bad stereotypes, they find crossdressing not funny at all and even offensive.

Crossdressing for comedy usually revolves around caricaturing and making fun of the other sex, albeit in a lighthearted way. And I think this is the case whether the crossdressing is male to female or female to male. When someone crossdresses and acts out the stereotypes of the other gender for laughs, it really reveals not only what the person acting it out thinks about what men or women are like, but also it reveals the thoughts about men and women of the audience laughing or not laughing. I do believe men and women are different (God made two sexes for a reason and the differences are beautiful!), and sometimes poking fun at the differences between the sexes is funny, even to me. This is just lighthearted fun, looking at the general differences between men and women that fit most people. I believe that there are general differences between men and women, beyond our physical bodies, that God made for us, and this is part of what makes us complementary sexes in the world and society, and specifically in marriage. But if the joking goes too far into unhelpful gender stereotypes, it ceases to be funny to me.

If someone thinks women are ditzes with no common sense who are paranoid only about how they look, then they would probably find it funny for a man to pretend to be a woman and act ditzy, with no common sense, being paranoid about how he/she looks. But someone who thinks this is an offensive view of women would probably be offended at the crossdressing which models this behavior.

We have to be careful to not overly prescribe the personality differences between men and women. The Bible talks about men and women having different roles, but it doesn’t say much about what the differences in temperaments or personalities or traits are. In fact, most of the things that our American culture designates as masculine or feminine are not necessarily so according to the Bible. For example, the fruits of the Spirit are all feminine traits in the stereotypes of our culture, and yet Paul holds them up for both men and women. So to be the masculine men God wants us to be, we should be like this – Galatians 5 – 22 But the fruit of the Spirit is love, joy, peace, patience, kindness, goodness, faithfulness, 23 gentleness and self-control.

I think of homosexuality and comedy in the same way. Sometimes people find it funny when a man imitates being a homosexual or makes homosexual jokes. But some people find these jokes degrading or offensive. I have lived in many different cultures, and even different countries throughout my life. In my experience, those communities that don’t know much about the reality of what homosexuals go through and feel find homosexual caricatures funny, and those that know what they go through do not find those caricatures funny, but offensive.

Overall, as a Christian, when I’m not giving into crossdressing for sexual reasons and sinning, I find crossdressing very much not funny, and very much offensive. It’s not funny and it’s offensive because of the false offensive gender stereotypes it reinforces. And it’s not funny because it is a sinful activity and why would I laugh at people who are sinning? In the same way I don’t think watching drunk people is funny, even in a movie. I don’t find it funny when people use the Lord’s name in vain. I don’t find it funny when people look at pornography. It’s true that even as Christians we can find sinful things as funny. But the more we grow in Christ, and the more we recognize a sinful activity as a sinful activity, the less we find it funny.