While living and working in New York, they met through a mutual friends circle. While on a quick visit to Chicago for a tonsillectomy , Liv's phone was blowing up, it was James texting to see how she was. He realized in her absence he'd developed a crush on her. When she returned, he told her while out on a fire escape at a friend's party. Three years later, after living together in the East Village and Williamsburg (and a summer in the Hamptons), they decided they were ready to move on from New York. With Liv from Chicago and James having an existing love for the city, the choice was easy, so they packed up their bags and a U-Haul and drove across the country to their new home. Three years later, with a home bought, a puppy adopted and Doobie the cat still melting their hearts, James popped the question.

After a fun day of sightseeing around Tokyo, Japan, James suggested they visit the Skydeck at Roppongi Hills before dinner. Confused why they would do that on a cold and windy night, when we were already running late for dinner, Liv agreed. Once at the top, James seemed distracted. Little did she know he was looking for a well lit location and someone who spoke English to take their photo (both challenging tasks). Finally he found a couple who spoke English. Olivia took her spot and when she turned to look at the camera, found James on one knee. After first asking James what he was doing, Liv then said yes!