[8] The site served people in Boston, San Francisco, Austin, New York City, Chicago, Washington, D.C., and Los Angeles.

[10] In April 2010, Time Out reported that the website was under construction for updates, but would remain free once it resumed operation.

Since August 2009, an "A-list" account option is available to users of OkCupid and provides additional services for monthly fees.

[23][24] The website added a bevy of nontraditional profile options for users to express their gender identity and sexuality in late 2014.

These options—which included asexual, genderfluid, pansexual, sapiosexual, and transgender categories—were added to make the website more inclusive.

[25] Through this addition, OkCupid popularized the concept of "sapiosexuality", meaning romance or sexual attraction based on intellectual, rather than physical, traits.

[26] OkCupid removed the Sapiosexual identity on February 11, 2019,[27] following considerable negative feedback, specifically quoting an article on Vice Magazine.

[28] In January 2018, OkCupid appointed Ariel Charytan, who was formerly senior vice president of audiobook and podcast company Audible, as CEO.

[29] In September 2018, OkCupid became the first dating app to create a dedicated space on profiles for LGBTQ daters to share their pronouns, and expanded that feature to all users in July 2020.

In that same month, OkCupid found that daters, coming out of the 2019 Coronavirus Pandemic, were looking for long-term relationships, negating the commonly held theories of a “hot vaxxed summer” (a play on Megan Thee Stallion single Hot Girl Summer) in which daters were looking exclusively for casual relationships.

[37] Additionally, a study published in the August 2018 edition of Science Advances by researchers at the University of Michigan and the Santa Fe Institute found that users of an unnamed, popular, and free online dating service in New York City, Boston, Chicago, and Seattle typically pursued potential partners ranked on average 25 percent more desirable than they were (as measured by the PageRank algorithm).

[44] In December 2017, OkCupid rolled out a change that would require users to provide their real first name in place of a pseudonym as was previously encouraged.

Although the company quickly backpedaled by saying that nicknames or initials would be acceptable,[45] the announcement was received with widespread criticism and condemnation for potentially raising the risk of harassment of individuals, especially women and minorities,[46][47] to doxing.

[48] It was pointed out that, unlike other dating sites that encourage the use of first names, OkCupid "encourages long profiles full of intimate details, including candid answers to questions about sex and politics", making connecting that information with a real name more problematic to users.

start-up, built a face database with images from OkCupid, due to common founders in both companies.

Amid the coronavirus pandemic, OkCupid reported a 23.4% decrease in monthly active users in the final quarter of 2020.

This may cause privacy problems for users who wish to leave an empty account before they delete it to avoid it being used for data monetization by OkCupid.