Wilkinson met Hugh Hefner at his 78th birthday party in April 2004, where she was hired to be one of the "painted girls" (women who are nude except for painted-on accessories). Hefner had apparently seen her picture, shot by photographer Kim Riley, on a fax machine at the Playboy Mansion and wanted to know who she was. Shortly after they met, Hefner asked Wilkinson to be one of his girlfriends, and he moved her into the Playboy Mansion along with her dogs Rascal (a Pembroke Welsh Corgi) and Martini (a Jack Russell Terrier).
She was featured on the E! reality television series The Girls Next Door, which followed the lives of Hefner's then-girlfriends: Wilkinson, Holly Madison, and Bridget Marquardt. She moved out of the Playboy Mansion in 2009 after meeting her future husband, Hank Baskett, and filmed her own spin-off reality show for E! called Kendra. The first season was about her living on her own and planning her wedding