He tells her she should go on dates with new guys who come to the beach, because one of them could be what she's looking for. "I feel kind of slimy making that decision or presumption for you," Dean says. This sounds like something he should feel slimy about, but it does seem like Caelynn is on a much different page than him, one that's much further into the book. In that sense, I do sort of understand why he wouldn't just stay in Paradise with her and hang out. In her confessional after he leaves, Caelynn says, "I thought he was my forever, but he blindsided me." That does sound pretty serious.