Guest Stars Eric Scott Ways as LJ Sullivan Brandon Victor Dixon as Demetrius Mercer Ron Canada as Wellington Spivey Tobias Truvillion as Jaha Michael Genet as Dr. Temple Co Starring Samantha A. Smith as Kellie Jamilah Rosemond as Keisha Mia Morgan as Kennedy Paige Herschell as Karen Friend 2 Gary Galone as Coach Mike Gail Everett Smith as Ursula Jemele Hill as Herself Malik Reed as Linebacker Brian Colin Foley as NYPD Cop 1 Gabe Bowling as NYPD Cop 2 Maria Taylor as Herself Michael Smith as Himself Cari Champion as Herself Jenny Strassburg as Karen Mike Rob as Goodwin Steve Belanger as Lead Hotel Exec. Atibon Nazaire as Cab Driver Chris Crowthers as White Guy Educator Jessica Bishop as Karen Friend 1 Bomani Jones as Himself