Guest Stars Marque Richardson II as Reggie Green Jemar Michael as Al Lucas Nia Jervier as Kelsey Phillips Obba Babatundé as Dean Walter Fairbanks Jeremy Tardy as Rashid Bakr D.J. Blickenstaff as Silvio Co Starring Courtney Sauls as Brooke Morgan Nicholas Anthony Reid as James Dickerson Brandon Black as Kordell Washington Luke O'Sullivan as Connor Taylor Foster as Becca Dan Bauer as Theater Kid Kendall Alexandria as Female Companion Dwight Edward Shields II as Cooler Black Kid Corey Livingston as Cool Black Kid Ayinde Howell as Barber #1 Denell Johnson as Barber #2