Alas, i'm way way too late to contribute to this interesting thread, and i wish i noticed it before.
Gender roles are sociocultural constructs. They do not come from biology itself, rather from an eventual division of labor that may arise from the reproductive differences between the sexes, and which in no way is intrinsic to the essence of masculinity and femininity.
In past times they weren't as near as all-encompassing, neither the labor division was as strict as we're led to believe in our modern times. While gender segregated societies were and are still a thing, their members do still have agency.
Gender only determines the way you're encouraged to express yourself by society, not by intrinsic qualities of gender itself, but as a political byproduct.
Conflating agency with masculinity and passiveness with femininity falls right into the fallacy of anatomical determinism, which in turn is subjected to cultural bias.
The biologic disparity in sexes that brings to a disparity of mansions is in the functions of conception and pregnancy. Such characteristics may bring differences of power in certain areas (e.g. human males develop to not gestate, barring ectopic pregnancies), but doesn't justify concepts of superiority, and in turn is not a disparity that necessarily favors the male of the species.
What is framed as active can be as well framed as passive.~~~
An analogy on the nice guy syndrome. Imagine children in a sandbox, a girl building a sandcastle. She is almost done, she is busy perfecting the very last final touches. A boy comes up to her and destroys her work. She is obviously not pleased.
She starts rebuilding, this time with a better foundation, a castle with a more compact shape, thought to withstand the whims of a jerk passing by, easier to protect. As she is almost done, that boy comes up again and destroys her castle for the second time.
She is pissed.
She moves to the opposite corner of the sandbox. As she is placing her things together to start her work again, a second boy comes up to her. He tells her he will protect her from the evil castle flattener, she replies with sure, whatever, i don't mind. She is focused on building, when the boy creeps up to her and says 'i'm protecting you, you owe me your lunch'. The girl refuses his request, on the basis that they never agreed on any reward, the boy has a meltdown and storms off.
A third boy comes up to her. He asks her if he can knock her castle down. She stands still, thinking about his request. She says yes, but only after she is done building it and after saying it is ready to be toppled down. They work out a plan together and eventually they start building more castles together and they both knock the things down.
The first boy is obviously a stand-in for abuse. The second is the 'nice guy' that fails to recognize the agency of the target of his affections and is upset when something doesn't fit into his rigid and transactional view of relationships. The third one is what you could call the authentic nice guy, that treats the girl as a true peer, but is seen by the 'nice guy' as no different than boy #1 ("He destroyed her castle! And she let him do it! She must be a masochist!").
Yes, but what if a girl is attracted to boy #1 instead of boy #3?
As for the conflation of jerkiness and attractiveness:
The mystery of those drawn to toxic relationships is not so much of a mystery as we think, they're drawn to the promise of growth they see in entering that relationship at that time (yet if it was true & healthy growth the relationship wouldn't be toxic in first place, but i digress..). They are also aware that the relationship can't last and/or is outright damaging, but still go for it because they see it as the only way, during that time, to nurture some aspect of themselves that they can't quite explain. This can happen to people of all sexes, genders, and sexual orientations.
On a sadomasochistic perspective:
The sadist projects onto another person his/her hypothetical pain to control its own, in a warped empathy with the goal of proving to him/herself that he can control his/her weakness by imposing it onto another, as a testament of one's own will and (imagined) strength to survive those torments they decide to inflict.
The masochist seeks rebirth outside of the human condition through the fetishization of privation and suffering, seen as necessary as negative counterparts for the existence of perfection (intended as the pre-birth eternal lack of need).
You could say they're two faces of the same medal and that deep down inside each sadist there's a masochist, and vice versa, since the sadist attempts rebirth through his/her victims, and the masochist controls his sufference through victimhood.. both looking at the other as only an extension of self.
This dovetails into the anthropological concept of primitive shame, which is deemed the powerlessness at the heart of the myth of total control oh-so-present in our western societies.
If you're interested in a way more articulate reading on the subject you can look up
pages 82-84 of this book or section VI of the .pdf 'Objectification and Ressentiment' by Martha Nussbaum, if it's still for free somewhere around the net.
Another interesting read that i feel is still related to the topic.. Norah Vincent is a journalist that decided to live 18 months as a man, and wrote a book about it.
While i'm usually very critical of identity immersion journalism, she makes some very good points about gender dynamics in dating, and it's well worth reading imho.
Here's an article about her experience.