Josie and Ryan first met in November of 2020. Their mutual friends, Bobby and Kelly Woblesky, kept bugging them both about this "perfect single girl" and "perfect single guy." Well, turns out it was a perfect fit. Bobby gave Ryan Josie's number and they texted for two months before meeting up in January 2021. Ryan spent many weekends driving up to San Francisco to visit Josie. They explored the city's bars and restaurants, cheered on the Giants, sailed in the Bay, and played nearby golf courses. In Summer of 2022, Ryan and Josie moved in together in Santa Cruz. Josie is happy to be closer to family and and Ryan loves how it doesn’t get hot and is still close to friends and family.
On July 14, 2023, Ryan and Josie went golfing with Josie's dad, brother, sister, brother in law, nephew, niece, and dad's best friend. On the 9th hole at Seascape Golf Course (after sinking a 15 ft putt), Ryan got down on one knee and asked Josie to marry him. After she said yes, Kathy and Mitzi ran down with champagne and their loved ones cheered from the clubhouse balcony. It was the perfect end to a perfect round.