It was created by Rebecca Odes, Esther Drill, and Heather McDonald as a resource centered on teen advice, body image, female sexuality, and other teen-related concerns.

Unlike teen magazines in the 1990s, Gurl.com was known for its humorous tone, unconventional approach to teen-related topics compared to mainstream media, and contributions from its audience (such as editorials and artwork).

Rebecca Odes and Esther Drill, childhood friends from West Orange, New Jersey,[1] conceived the idea of managing a magazine while they were in high school,[2][3][4] as teenagers in the 1980s.

[5][6] Dissatisfied with the teen magazines available to them growing up, they sought to curate alternative media that would properly address the concerns of teenage girls.

[8] The clothing retailer Delia's approached Odes, Drill, and McDonald with an acquisition offer and purchased the website in December 1997.

[4] Gurl.com was included as part of the website network iTurf (Delia's online subsidiary) in an attempt to launch an e-commerce market targeting Generation Y.

[34] Unlike contemporary online communities aimed at young women in the 1990s, Gurl.com had an edgier appearance,[9]: 154  using a frank and nonjudgmental approach to address topics such as dating, health, and beauty.

"[2][37] Because Odes, Drill, and McDonald believed that girls prefer creating to being consumers, the website allowed contributions from its users, such as comics, poems, opinions on current events,[9]: 154  and reviews.

[2][4] One of Gurl.com's notable contributions from its readers was its comics section, which included serializations such as Those Sucky Emotions and Mizbehavior, both initially listed in the "Deal With It" topic.

[45][47] They published a series of teen advice books based on the editorial content on the website and also included conversations found on Gurl.com's message board.

A Whole New Approach to Your Body, Brain, and Life as a gURL, was released on September 1, 1999;[2][7] it offered advice on puberty, queer identities, sex, eating disorders, drug use, and mental health, with a list of resources on each topic.

[48][49] To promote the book, Odes, Drill, and McDonald launched an accompanying website, DealWithIt.com, which hosted an online version of the resources.

[57] Harry Wessel from The Orlando Sentinel described the book as one that would help teenagers make good choices about their future and said that, despite its branding, its advice was also applicable to men.

[37] Janelle Brown from Salon.com noted that the accessibility of sex education online had prepared young girls and also allowed them their own sexual agency.

In 1999, Salon.com stated that anti-pornography advocates cited concerns that young girls discussing and having accessibility to sex information would lead to an increase in underage sexual activity and be harmful to their development.

[60] Abstinence advocate Coleen Kelly Mast argued that Gurl.com gave a one-sided view of human sexuality, claiming that the information would not help lead to "satisfaction in marriage".

[62] In 2015, the Canadian Broadcasting Company included Gurl.com among 1,494 websites and mobile apps that were privacy concerns, as it allowed children to unknowingly list too much information about themselves.

In a study conducted by Media Metrix and Jupiter Communications in 2000, there was a 125% growth of girls aged 12–17 years old using the Internet, which was partially credited to Gurl.com.

[71][72] In a study done by professors Barbara Duncan and Kevin Leander in the same year, they observed that because Gurl.com already had an established network, girls who hosted their website at Gurlpages could easily connect with one another and receive feedback on their work.

[34] In 2005, scholar Sharon Mazzarella noted that Gurl.com was among the websites that helped girls be creative and empowered, though there was later increasing moral panic surrounding how harmful messages may influence them.

[17]: 141 Scholars Ashley D. Grisso and David Weiss noted that users on Gurl.com's message board often discussed their interest in sex, usually respectfully as per the established norm on the website.

[17]: 36, 41, 45  A study published in the Journal of Computer-Mediated Communication in 2006 found Gurl.com to be the best example of a female-centric website that encouraged critical thinking skills in young girls through their discussions on current events.

It was named as a site that inspired the growth of websites owned by teenage girls, creating a potential advertising market worth US$15 billion in 2000.

[73] Duncan and Leander argued that Gurl.com created spaces of both "resistance and conformity", as people who had websites on Gurlpages both expressed themselves in creative writing yet also listed personal information identifying their demographics and consumer habits.

[9]: 157  Echoing Duncan and Leander, she commented that while Gurl.com had a disclaimer stating that their views do not represent their advertisers, the website may have been "packaged for a homogeneous idyllic audience commodity", which contrasts with the "utopian sentiments" of an online community.