The lucrative cinema business of the classical Hollywood brought up the emergence of a category called the woman’s film, recognizing an increased economic potential in creating a genre that would favor the affinities of the female cinemagoers of the time. It could be soon recognized that the woman’s film had similar characteristics of a genre today known under the name of chick flick. However, the transition from the woman’s film to chick flick was not a straightforward process. Nevertheless, the 1990s marked the beginning of almost two decades of heightened popularity of chick flicks. In this work, I provide a brief insight into the representation of women through female characters in some of the most popular chick flicks from the beginning of the 21st century. By analyzing the characters, circumstances, and the extent of chick flick’s influence on contemporary women, I set a ground for a more concise examination of the female characters in recent chick flicks, specifically the movies How to Be Single (2016) and Isn’t It Romantic (2019). These movies show a detachment from the typical conventions of the early chick flicks and take a new approach towards the stereotypical depictions of women, romance, and love characteristic of this genre. They show a generation of young women whose visions of life and success are somewhat a product of the chick flicks they grew up watching and confronted with a world that is not as idealistic as they thought, they are forced to set new standards for women by carving their own paths to self-fulfillment.