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I know some guys dress like girls... but pink pumps with a yellow dress? C'mon... even my dad can colour cordinate...

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I'd actually be somewhat interested... someone who's confident enough to walk around in public wearing clothes that society looks down on. I would be too embarrassed to go out in public with him though (I am VERY shy and don't like people looking at me), but there's nothing wrong with a guy who wears women's clothes. No one judges a woman who wears men's clothes... it's a double standard! Also, transvestites are straight 90% of the time, no matter what other people claim.

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...I think OP meant that the "guy" was just a very masculine looking woman. Her nickname is "badatgenders"... so that's the impression I was left with.

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I agree, Null. This guy - or butch woman, whatever it was - has really awful taste. Therefore, their future children would have bad taste, and grow up to be ridiculed and shunned, and finally be put in the loony bin. OP and Dress Man would have to constantly be there to take care of their fully-grown, crazy children, and become utterly stressed from the kids being so clingy and dependent. OP and Dress Man will eventually break from said stress and go insane themselves. And this is why OP s

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I wouldn't. Yellow dress and pink pumps? Those don't even match. I'd hate to see what other kinds of things he/she owns.

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Actually yellow and pink match well and are a popular combination depending upon the shade of each color. Anyone here ever heard of sun dresses or pastels?

Cross-dressing man, or man-looking woman who likes other woman... It shouldn't be THAT hard to tell.

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I'm not sure if she's going girl. She might be going cross-dressing man tonight! (Commas are your friends, silly.)

It's probably best you don't date. Imagine if he came to pick you up and you were both wearing the same dress...AWKWARD. But also VERY HAWT!

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It could've easily been a hazing. For instance, if he is a rookie on a sports team, they are made to do some interesting things. I know a university team where every rookie has to wear women's underwear and run around down town, then play a game of football in the park (still in underwear) but at least they get rewarded with a massive party at the end of it

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