Jacob and Olivia first met at Madison Middle school. Jake had a crush on Olivia back then, but Olivia did not know it. When she thinks of Jake, she remembers his Justin Timberlake blonde highlights & that he was a full head shorter than her. She was friends with both of Jake's best men, Jakob Konen & Eric Swenson. Fast forward 10 years to the summer of 2016 Olivia was working with Katherine (jake's little sister) at Fitbar Cafe in West Seattle. Katherine invited Olivia over for lunch one day after work. As Olivia & Katherine were eating their quesadillas on the Gregor back porch in walks 21 year old Jake, off early from his summer job at a construction company. The first words out of Jake's mouth as he entered the back gate were "Olivia Gass" to which Olivia replied (slightly confused by the use of her full name) "Jacob Gregor". Jacob then proceeded to, as he says, "turn on the charm" asking her how she had been. Now Jake had just come home from working on the job site so he was markedly dirty. He told the girls that he was going to go shower and a few minutes later he was back outside claiming the water was not working in the house. So naturally, he took off his shirt in front of them and grabbed the outside watering hose, and proceeded to shower himself. Jake thinks that this is where he piqued Olivia's interest. But in truth Olivia had seen some pictures of him during the summer through Katherine's Instagram and was already interested in meeting him- she knew it was just a matter of time. Later that night Olivia and Jake met up at a party on Alki and the rest was history. They began officially dating on September 8th (Olivia's parent's wedding anniversary) to which her dad replied when he found out "That is our anniversary, pick another one." They didn't. Jake and Olivia began a long-distance relationship 2 weeks after that as Jake was finishing his degree at Western Washington University in Bellingham and Olivia was in Nursing school at Seattle University. After graduation, Jake moved back to West Seattle and they started planning their 3-week trip to Vietnam. A couple of years later they moved into their first apartment together and adopted their crazy son Captain. Jake proposed to Olivia on the beaches of Maui in October 2021 and a month later they began their travel nurse journey. They have driven their Subaru through 35 states and have lived in California, North Carolina, and now Oregon. They hope to continue their journey to Colorado, Chicago, and back to California before settling back home in West Seattle.