Da'Vine Joy Randolph promotes her movies "The Holdovers" and "Rustin." Tyla discusses her single "Water." Jennifer welcomes high school senior and future first-generation college student Dana Bolden from Jackson, Mississippi, who recently made headlines for being awarded over $2.2 million in scholarships from more than 50 colleges. Dana feels proud to be able to represent her community and said it is rare to see positive stories coming out of her neighborhood.