Feeling concerned that he didn't completely win over Adrianne's family in Joliet; Chris is starting to feel insecure in their relationship. His worry that he may lose her causes him to deter Adrianne's attempts to find her own apartment and deletes messages from realtors trying to contact her. To prove his love for her, Chris surprises Adrianne with a trip to Puerto Rico to give them a chance to reconnect and spend some quality time together. Easily impressed, Adrianne is blown away with all the island has to offer; especially the first-class accommodations. It's two days of love and exploration as the pair traverses their bedroom, a multi-million dollar yacht and the streets of Old San Juan. The lush, tropical setting casts a spell over Adrianne and leaves her longing for a permanent commitment from Chris. Unaware that Adrianne is looking for a ring, Chris takes her out to an aphrodisiac restaurant. When the owner questions why the couple isn't married, Chris is put between a rock and hard place. Does he propose now, even though he isn't ready, or does he break Adrianne's heart?