When I was in undergrad at my second college (I transferred twice before getting my B.S.), I took a class called Human Communication. The point of this course was to discuss communication methods commonly used in all aspects of contemporary American life. One of the books we were supposed to read during that semester was called You Just Don't Understand: Women and Men in Communication.
Perhaps the most interesting thing I can remember learning is that men and women ask for things they want differently. An example from the text: Three boys and three girls were given toys to play with. When a boy wanted a toy that another boy had, he asked for it directly. When a girl wanted a toy another girl had, she tried to use the third girl as a way around asking directly (e.g. Jenny telling Sarah that Erika wants to play with the doll Sarah has, when it's really Jenny who wants to play with it).
Books like this are worthwhile for two reasons. First and foremost is that it allows male and female writers to get a picture of the different ways men and women communicate inside gender groups and with each other. It's a good resource to have because, let's face it, we're going to default to our standard communication styles. For a man, that tends to be more direct and upfront. For a woman, it's more circumspect and subtle.
Perhaps more interesting than knowing these communication styles is knowing that people will have difficulty understanding if the communication style is not the one they use. Hence why the stereotypical American male is said to not understand subtlety. This is the number one offense I've seen in my scant experience with male romantic characters. They understand the subtlety of the female main characters far better than any real man typically would.
There are, of course, men and women who break the mold. My wife is, in general, a very plain-spoken woman and not prone to subtlety. My friends Casey and Alice* are the same way (a big reason why they're my friends). By contrast, my male friend Gary tends to be more circumspect.
What does this mean for the female writer trying to write a male character or a male writer trying to write a female character?
Pay attention to how men and women typically talk.
A stereotypical guy will tell you up front what he means (unless it's emotional, then he tries to play it off like it's no big deal). A stereotypical girl might speak more in hypotheticals and try to get answers to a question she's not asking. When these two get together, sparks are more likely to fly from him misunderstanding what she's asking rather than any understanding on either part. Especially when it comes to romantic entanglements.
The end result of all this? A guy will say direct things that he doesn't realize are the wrong answer because he doesn't know what the girl's really trying to ask.
Does this mean you have to make all men dense as a brick wall or all women capable of verbal gymnastics? No, of course not. In fact, you might get an interesting story out of flipping communication styles between a man and a woman. However, you the writer do need to pay attention to standard methods of communication when you're writing male and female characters. That's what (I hope) you take away from my rambles.
What are your thoughts on this, dear readers? Agree? Disagree? Want elaboration? Let me know in the comments.