With her lease expiring, Jenny responds to a Facebook Marketplace ad seeking a new housemate. With fate on Jon's side, Jenny neglects to click "read more" and shows up for a tour, blissfully unaware that the other 4 occupants are all male engineers. Jenny thought that living with the guys would be "less drama", but by fall Jon had a massive school-boy crush on her.
In his first attempt at some quality time together, Jon asked Jenny to be his "instagram boyfriend" for the day. Jenny accepted the role and they spent the day visiting all of Jon's favorite hidden spots throughout the Snoqualmie Valley. The day even featured a completely accidental run in with Jon's family, who just happened to driving by and snapped some quick undetected "paparazzi" photos. New profile pictures, some bonus candids, and more dates on the horizon! After several dates, Jon passed thorough examination from "The Aunties". This council of Jenny's friends decided that he was finally qualified to become Jenny's boyfriend. They began officially dating January 2021.