They became friends when Madi moved back to Marin. Once Madi was in San Rafael with Ryan they started hanging out. They would get accidentally thrown into awkward yet hilarious situations where Madi saw how patient and kind Ryan was. Ryan quickly noticed Madi's loving and fun attitude. As they spent more and more time with each other their friendship became stronger and they began texting and talking to each other daily.

Over time their friendship grew into stronger feelings. In May of 2025 they revealed their feelings for each other the day before Ryan left for a trip to Japan. After three long weeks of waiting and deep contemplation they began dating when Ryan returned home in June.

In December of 2025 Ryan and Madi knew they were meant for each other. Ryan had a ring made and secretly planned the perfect proposal with the help of his close friends Dapo and Kevin. On January 4th 2026 Ryan proposed to Madi at that the Palace of Fine Arts in San Francisco.