They worked together for a few months prior to dating. On the 9th of April in 2015, Jake decided that he was going to ask Yoshimi out in a grandiose type way. He had his parents set up a bouquet of flowers and a card with her name on it on a dock in Kirkland and had them hide to take pictures of him asking her out. As Jake and Yoshimi walked out onto the dock the wind had blown over the card and so she didn't notice it until Jake awkwardly pointed it out by picking it up and saying "Oh, this has your name on it." It was a cliche way of starting out, but the memory will last a lifetime.

For the Christmas of 2016, Jake and Yoshimi decided to head over to Japan so that Jake could meet Yoshimi's grandfather and friends and also so that he could see where she grew up. Jake had been planning prior to the trip to get her a Christmas gift she wouldn't forget and in doing so recruited the help of her friend David to take pictures of them so they could remember their trip together. Under the guise of a "photoshoot" two days before Christmas, Jake and Yoshimi went to a park across from the church where Yoshimi had grown up in and they started their "photoshoot". Near the end of the shoot, Jake got down on one knee and asked Yoshimi to marry him. With a stunned look on her face, the first words out of her mouth were "What are you doing?". This was followed by terrifying 5 seconds of silence for Jake until he asked again to clarify which was then met with the answer of "YES!".