The story of Hilary and Joel's romance is a series of serendipities. The two grew up in Washington only a few miles apart, but didn't even meet until they were adults living in San Diego attending different schools: Hilary working toward a career as a nurse practitioner and Joel garnering a degree in business. It all began in 2006 with a friend's wedding in Costa Rica. Hilary's sister, Kirsten, and her now husband, Levi, met at the destination wedding. They began dating and taking trips to San Diego where Kirsten would call Hilary to hang out while Levi called his friend, Joel. The foursome enjoyed one another's company a few times a year. Hilary and Joel developed a flirtatious friendship, but kept dating other people. Finally Hilary and Joel began spending time together as friends without Kirsten and Levi.

Their other relationships fizzled out, but their friendship blossomed into romance. On the day of Hilary's ten-year high school reunion in July 2013, Joel left the house for a few hours claiming to go to the grocery store. Later that day the couple boarded the Bainbridge-Seattle Ferry to the reunion along with a few friends. It turned out earlier that day, Joel had visited Hilary's father to ask for her hand in marriage. He gave his blessing. Joel proposed on the Washington State ferry that day, just as Hilary's father had proposed to her mother on a Washington State ferry so many years before.