Five women embark on a journey to Italy with Diann Valentine. The women are in different stages of their lives in regards to love and the unique stories they tell, but they are all in the same boat when it boils down to dating as black women in America. The women must face their fears, move on from their emotional baggage and also understand cultural differences as they seek new love in Rome. D. Micah Lindsey and Christine "Cece" Counts join them to offer their own insights about love while educating them on the Italian heritage, and they help Valentine vet the perfect bachelors.
Diann gives the girls one more chance to make some big decisions regarding their relationships; Shay goes on a final date with Emiliano; Ashley decides to take a big step with Alejandro; Alberto reveals something to Nakita that throws her for a loop.
The girls plan to make Gina's 52nd birthday a big celebration; Mercedes seeks Diann's advice for a romantic dilemma; Alejandro's actions spark jealousy from Ashley; Nakita goes on a fourth date with Alberto.
Diann finds out that Mercedes has been talking to a potential suitor; Shay looks for a spark with Emiliano; while on a double date, Claudio, Gina, Ashley, and Alejandro visit a magnificent vineyard; Diann gives Mercedes some hard truths.
Mercedes talks about her past and why finding a man who loves Jesus is so important to her; Ashley and Alejandro go on their second date; Diann introduces Nakita to a guy at the beach; Shay goes on her second date with Emiliano.