Their first conversation was a lively debate in Gumby's Pizza over the artist Jackson Pollock. From there they got to know each other better during an ice skating trip with friends, where it was only because of Sydney that Jackson ventured off the wall. They saw each other often through RUF and their friend group's volleyball games and art nights, until the fateful series of events where Jackson first broke Sydney's right thumb during volleyball (a subject of further debate, as he states it was a shared effort) before asking her on their first date the next morning. Sydney knew she was in love when just two weeks later, he broke his left thumb at the same volleyball courts. And so hand in hand (sometimes cast in cast), their relationship began. Almost two years later, overlooking Canterbury Falls in Ontario, Canada on a snowy December morning, Jackson asked Sydney to marry him, and she of course, said yes.