Meredith packs to go off to Puerto Rico, where she will have overnight dates in different cities with all three remaining men. Meredith confides that she is excited, and plans to really get to know these guys, but is also scared, as she's never dated three guys at the same time before. First Dream Date: San Juan With: Ian Meredith greets Ian atop an old fort in San Juan, hoping to learn more about how he feels about her. The two spend the day playing and flying a kite, and Meredith confesses that with Ian, she feels very relaxed. Ian has the goal of opening up and letting Meredith know how he feels about her. Meredith tells Ian that she, too, is not a great communicator, and that when she says something, she means it. Ian kisses her, and tells her that's how he communicates. Ian confesses that when Meredith talked about not being a great communicator, it made him smile, as he is dealing with the exact same issue. After spending the day out and touring Old San Juan, they meet again