Ashley Blaine Featherson-Jenkins (née Featherson; born December 4, 1987)^[2] is an American actress. She is best known as the co-creator and star of Black&SexyTV's Hello Cupid. She also appeared in the web series Roomieloverfriends, the film Bad Hair, and was a main cast member on the Netflix series Dear White People (2017–2021).^[3]

Born Ashley Blaine Featherson, she was raised in Gaithersburg, Maryland.^[4] She first acted at age four in a school production and enjoyed it from that age.^[5] When she was 14 she began to perform at the Studio Theatre in Washington, DC and studied under costume designer Reggie Ray.^[3]

Featherson attended Howard University and graduated from the Fine Arts department, where she majored in musical theater.^[5] She is a member of the Alpha Kappa Alpha sorority.^[3] Featherson has stated that she most admires the career and work of Vanessa Williams.^[6]

Featherson co-created the web series Hello Cupid with Lena Waithe in 2012.^[2] The show was distributed by Black & Sexy TV and eventually rebooted.^[5] Featherson also starred in the series opposite Hayley Marie Norman.^[3]

Her first feature film role was in Justin Simien's Dear White People in 2014.^[3] She reprised the supporting role of Joelle in the 2017 Netflix television series adaptation of the same name.^[7]

She co-starred in the 2018 web series Leimert Park, which premiered at Sundance.^[8][9] Featherson also appeared in the re-creation of the photograph "A Great Day in Harlem", organized by Netflix's Strong Black Lead initiative.^[10]

In 2020, she collaborated with Simien again on his comedy horror film Bad Hair. That year she also worked with The Lip Bar on a makeup campaign.^[11] She also helped develop a three-piece collection for dark skinned women with Mented Cosmetics.^[11][12]

Featherson announced her engagement to sports agent Darroll Jenkins in September 2020, and married him on September 5, 2021, at Hummingbird Nest Ranch in Santa Susana, California.^[13][14][1] Longtime friends, they began dating in 2018.^[15]