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

Torn between Matthew's stability, warmth and protection and Ian's instability, passion and sense of adventure, she takes them home to meet the parents. Matthew Meets the Family First, Meredith spends an afternoon with Matthew on a river cruise in Portland OR. Looking forward to meeting the family, Matthew declares he's ready to consider marriage as long as she's ready. She won't open up, saying she's been hurt so many times. He wants to protect himself too, knowing he's not the only one. Then, on to the family â€" the parents, brother and uncle. Her Dad's impressed when, under questioning, Matthew says he sees something in Meredith's eyes and smile that makes him want to be there. Meredith tells her family she's never met anyone like him, that she feels safe and secure with him. Dad notices that Meredith is glowing and her brother, who had been a skeptic, says Matthew has more intelligence and personality than he'd suspected. After dinner the couple snuggles on the couch.