Both there for different events, Josh and Pilar first saw each other at a local restaurant on Guam on August 11th, 2021. Pilar was finishing dinner for her sister Gia's birthday, and Josh was arriving for his friend's whiskey night. Although they never spoke to each other that day, they both remembered the other. Being on a small island sometimes has its perks! Through the grapevine of mutual friends and golf acquaintances, Josh asked for Pilar's number through her sister. Gia asked Pilar, "Do you remember that white boy with the Sinahi?" and a few days later, they were on their first date. After that day, the rest was history. Josh soon relocated to Hawaii for work and Pilar made the decision to follow him there. So many memories were shared and after just a couple months, she decided to move in completely. After a year of living together, Josh was deployed for six months. Pilar and their dog, Athena, waited patiently until his return.

Pilar's favorite holiday is Christmas and they both really wanted to celebrate with family while they were still on the beautiful Island of Oahu. They invited both families to come out for the holidays. Pilar had made a trip to see her parents in Maryland for Thanksgiving and while she was away, she tasked Josh with finding the perfect tree. Sneakily, Josh hid the engagement ring inside the tree and put the lights on, saving the decorations portion for Pilar when she returned. All throughout decking the home with Christmas spirit, Pilar never saw the small box hidden, waiting, inside the tree. Christmas Day came, and everyone had a wonderful morning. After all the presents had been shared, bellies were full from breakfast, football was on the big screen and the smell of dinner cooking flowed through the apartment. Josh then announced that they had missed one last present. As Pilar pulled the box from the tree, Josh got down on one knee in front of Pilar and both their families. He popped the question and of course, she said YES!