"In this way Wollen directly politicized the sad girl and put her expression of suffering onto a larger scale. In interviews Wollen expressed discomfort with βthe hyper-positive demands of contemporary feminismβ that is fixated on self-love, approval, and βmaking it cool and fun to be a girl.β The problem with this, for Wollen, is that βit isnβt really cool and fun to be a girl. It is an experience of brutal alienation and constant fear of violenceβ" (Thelandersson 171).
The creation of the βsad girlβ in a sense takes back this notion of feminized sadness. Modern feminism, though it has created progress, frequently pushes aside the truth that existing as feminine can be dangerous and frightening. This is not to say that being feminine is bad, per se, but instead to acknowledge the frequent violence, both physical and social, that feminine presenting people undergo. The sad girl aesthetic is, in a sense, a direct counterpoint to that of the "girlboss," a woman who is successful and happy through her financial or career-based success.
The "girlboss" is smart, independent, and doesn't need a man in her life, but at the core of her existence is her success in a male-dominated space. In order for her to exist, she must be the one in a million chance, the exception that proves the rule--that is, the fact that men tend to dominate the corporate sphere.
The "girlboss" notion of feminism brushes aside the very real issues surrounding gender in the workforce: unequal pay, segregated labor markets, sexual assault, and more. The girlboss ignores all of this, focusing on personal achievements in the face of an unequal society, ignoring the wider structural issues in favor of an individualized success story.
The "sad girl" acknowledges the existence of the "girlboss," but with the distinct understanding that her image is unrealistic and practically unattainable. Most women will not, and in fact cannot achieve this ideal image, and that can be disheartening and sometimes even downright depressing.
Thelandersson later expresses a facet of how this correlation between sad girls and disillusionment with traditional social structures might come to be: "By inserting political analysis into the stream of sad girl content on the platform, followers learn to associate also critical, anti-capitalist, thought into the experience of mental illness, and connections can possibly be made between personal suffering and larger, structural issues" (Thelandersson 183).