I think it's more difficult for a woman, primarily because women are supposed to be the stereotypical 'emotional' gender.
Before I proceed, I will state that I'm a female.
Several online tests tell me I think like a man (I know they're not scientifically accurate, but they're still fun to take).
My dad used to jokingly refer to me as his 'son', simply because I wasn't emotional like my sister was (and I also had no interest in dolls, frilly dresses or any of the other things little girls like to do).
My friends were primarily boys, simply because I was able to relate to them far more than I could ever relate to girls.
I've had men refer to me as 'a buddy', and several have told others that I'm 'cool', and that I'm 'one of the guys'.
I don't understand women in general, because many of them are emotional, and they react emotionally, whereas I always favor logic. Then again, most of them don't understand me, either.
Strangely enough, men will sit down and discuss things with me that they'd never discuss with other women, and most women avoid pouring their problems on me because I don't react they way they want/expect me to.
Overall, I'm happy with who I am, but I'd be lying if I said it hasn't been difficult over the years. Once people get to know me, most of them think I'm okay, but most people don't quite know how to 'take me' when they first meet me. I don't fit the female stereotypes, and it does throw them off.