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 and her love team host a rooftop mixer at one of Rome’s most exclusive hotels for the girls to mingle with a crop of eligible bachelors. Shay is introduced to Roberto, a charming chef but will her past come back to bite her? Mercedes wants a man who loves the Lord yet falls but is attracted to a hunk with swag and a man bun. Sparks fly between Ashley and a sexy lawyer while Gina connects with Dario, a distinguished gentleman. Meanwhile, Shay and Ashley continue to butt heads.
Love Expert Diann takes the women to the Italian Derby for the first time. As they revel in being black women in a sea of Italians and being accepted for everything they are, Diann introduces them to various men. Mercedes continues to be difficult, while Shay basks in the attention from two suitors and Nakita has some misfortune. Meanwhile, Ashley goes on her first date with Leo and struggles with her past. As they spend more time together, friction between the women mounts causing them to call a house intervention with Shay.
Fresh from their house confrontation, Ashley and Shay agree to disagree. Meanwhile, Nakita continues to struggle with her self-esteem but Diann hatches a master plan to get her out of her funk. While the Love Team devises a new strategy to figure out what picky Mercedes really wants, Ashley discovers disturbing new information on Leo’s social media, which she can’t seem to shake. As Gina gets more comfortable she finally opens up to the girls about her past.
With pending concerns from some suspect social media posts, Ashley confronts Leo about his intentions. Love Expert, Diann and her team take the women to Villa Borghese, one of Italy’s most romantic landmarks. With only a few weeks left, she wants the ladies to make some real choices. Diann notices that Shay is having a little too much fun. Nakita’s prince charming may not be quite the man she thought he would be. Gina gets cozy with Claudio and Mercedes shocks the team with an unexpected addition to a group outing.
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.
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.
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 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.