May the Best Man Win - S5.E17

Whitley organizes a campus fundraiser and tries to wrangle donations from prominent business people. She hits it off with Byron Douglas III, a successful alumnus who owns a restaurant chain. He is impressed by her powers of persuasion, and asks her to assist with his campaign for state senate. Whitley and Dwayne quarrel after she belittles him in front of Byron. Mr. Gaines learns that he is about to lose the lease on the Pit because a corporation outbid him. Byron, a former Pit employee, uses his campaign rally to elicit support for Mr. Gaines. The corporation's representatives decide to seize the opportunity for positive publicity by underwriting Mr. Gaines' lease and letting him keep running the place. Whitley and Byron share a kiss.