Ashley recently went on four dates with the same guy. She gave him chances because he was good on paper and respectfully asked her out. She describes her third date when she felt it necessary to kiss a guy she didn't want to kiss for the first time. They then fast forward to their fourth date, on Valentine's Day, when she became officially grossed out. Jared joins in on the conversation and talks about the best moves to make in this situation, who should be paying, and transparent facial expressions. Fellow Bachelor in Paradise friend Carly Waddell calls in and discusses how she went from grossed out to friends to an engaged couple with fiance Evan Bass. She gives her advice on what to do in a situation you "don't feel" at first.
Ashley and her special guest, The Bachelor's Jared Haibon, discuss what guys really mean when they say “let’s take it slow” or what it probably happening when a girl is “confused” in a relationship. Jared discusses why “games” normally have to be played in dating. Jared tries to teach Ashley how to have confidence when a guy she likes makes her nervous. Ashley and Jared then reminisce about the most memorable moments of their relationship, like when she threw up in his car, when he found her the most attractive, and the Bachelor in Paradise letter.
Has someone ever said "You're so pretty and smart... why are you still single?" Well, the Iaconetti sisters delve into reasons women tend to push away the nice guys and say come hither to the bad boys. Ashley analyzes her inability to crush often, and particularly crush on guys who reciprocate feelings towards her, while also asking for some advice in a current dating scenario. Lauren discusses her dislike for traditional courting. The girls also discuss the discomfort, nervousness, and dread that come with the beginning stages of a romantic relationship.