Balancing gender roles

My Sassy Girl was released in 2001, the same year as Friends. Unlike Friends' male characters, Gyeong-woo's character is pathetic. He appears to be emasculated by the too-powerful presence of the feminine character, yet not exactly femininity itself.  

What is femininity? Is it the image of a soft, pretty, sweet, long-haired young woman who can play piano or an authoritative, assertive woman who is not shy to put you back in your place ? In contrast to Hae-joang Cho's discussion about women roles and their assertiveness, I feel like the Girl's aggressiveness in the movie functions as a mask to carry out the mother's generation's ideal femininity. I'm compelled by this because her initial problem was the loss of her lover. In showing her depressive, emotional self, she functions as neither.

Then, what is masculinity? Powerful, successful, loyal gangsters? Like Friends, there were no examples of masculinity from the older generation in My Sassy Girl. Gyeong-woo's father doesn't impose any authority over him and the Girl's father passes out every time he needs to assert his authority. Then does Gyeong-woo seem pathetic because he is not a gangster?  

His visits to the prison and his interactions with other inmates shows exactly his masculinity. 

Although he's not powerful, he's not threatening, he maintains his honesty. The development of this character changes the way how we see masculinity. By displaying care and maturity, gaining success (using her and their story as an idea for a script) and loyalty (replaced stricken-down tree, writing about their story), his masculinity is redeemed without turning into a gangster.  

Although the gender role reversal is supposed to be humorous, but I hardly find it funny. I found it rather humiliating and degrading, as it would obviously be if the gender of the characters swapped.  

The difficulties that each gender go through may not be identical, but in the modern world, I would feel like they are equivalent. A girl needs to dress up and wear heels, the guy has to be successful and trustworthy to gain the trust of her parents. Not one has it easier than the other. Then, these characters might only be displaying allusions of what we think are gender roles and not their true functions.