It's A Mann's World (2015)

S2E7 Mann and the City

When Tamela receives a prestigious award in New York City, she seizes the chance to transform David into a sophisticated urbanite. Meanwhile, David takes it upon himself to test Tiffany's new boyfriend, putting him through a series of challenging situations. As Tamela navigates the bustling city life and David confronts the new relationship, both face unexpected trials that could change their perspectives on love and success.