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.
Ashley confronts Leo about his intentions; Diann and her team take the women to Villa Borghese; Nakita's Prince Charming may not be quite the man she thought he would be; Mercedes shocks the team with an unexpected addition to a group outing.
Ashley and Shay agree to disagree; Diann hatches a plan to get Nakita out of her funk; Ashley discovers disturbing new information on Leo's social media; Gina finally opens up to the girls about her past.
Mercedes continues to be difficult; Shay basks in the attention from two suitors; Nakita meets with some misfortune; Ashley goes on her first date with Leo while struggling with her past.
Shay is introduced to Roberto, a charming chef; while Mercedes wants a man of faith, she is attracted to a hunk; sparks fly between Ashley and a sexy lawyer; Gina connects with Dario, a distinguished gentleman; Shay and Ashley continue to butt heads.
A rivalry over men develops between Ashley and Shay; Gina, a former Food Network star, has trouble finding her footing.