S1, E8: After a devastating goodbye to a woman he loved, Gerry enters a landmark week on his journey, heading to Costa Rica for overnight dates. Emotions run high as each of the remaining two women contemplate the significance of the days ahead, but it’s Gerry who will need to reckon with the consequences once he says “I love you” to both of them. Difficult conversations lie ahead for the couples, but will the long-anticipated alone time with Leslie and Theresa offer the clarity he needs to get down on one knee, or will he be left as confused as ever?