Playboy model Kendra Wilkinson confirmed her break up with Hugh Hefner in early October 2008. According to E! Online, Hefner played an integral role in arranging the engagement between Wilkinson and her new boyfriend, Philadelphia Eagles receiver Hank Baskett. E! Online: Kendra's Wedding Scoop: "Hugh's Running This" (November 7, 2008)

Wilkinson, who was one of three girls said to be romantically linked to Hefner, made the statement on The Chelsea Handler Show on October 7, 2008, that "she and Hefner will always be friends."PerezHilton: Kendra Confirms Hef Break Up (October 8, 2008) Hefner has also played a supportive role in Kendra's upcoming wedding.

In a US Weekly interview, Kendra opened up about life inside the Playboy Mansion.NY Daily News: Hugh Hefner's Playboy Lifestyle Isn't What It Seems (January 14, 2009) Reportedly Hef requires all his live-in girlfriends to sign in and out in a records book which Hefner analyzes every morning to keep tabs on their activities.NY Daily News: Hugh Hefner's Playboy Lifestyle Isn't What It Seems (January 14, 2009) Each week, Kendra and the girls receive $1,000 a week and are highly encouraged to stay in for the holidays to be with Hef.NY Daily News: Hugh Hefner's Playboy Lifestyle Isn't What It Seems (January 14, 2009) Also, verbal contact was sparse and she did confirm that her relationship with Hef was intimate.NY Daily News: Hugh Hefner's Playboy Lifestyle Isn't What It Seems (January 14, 2009)