Jason invited Robin to a first date of rollerblading at Skate Estate on a Wednesday night. Robin brought her own rollerblades, and in a naive assumption that there was no way this girl would be able to keep up with an ex-hockey player, Jason resorted to rental skates. To his surprise, he struggled to keep up while his feet were in pain. They alternated skating and talking, and quickly realized they were a perfect match. Jason ended the date with a kiss in the parking lot and secured a second date.

The day before Father's Day, Jason and Robin went to "The Luce Ranch" to celebrate Father's Day with Jason's parents. Before they sat down for lunch, Jason suggested that he and Robin take the dogs for a walk in the woods (as they normally do) to help the dogs settle down. As they walked down the hill into the woods to cross the creek, via the gorgeous custom bridge made by Jason's father, Robin was cluelessly watching her step and looking at the ground. When she finally looked up half way across the bridge, the railings were lined with dozens of roses leading to Jason at the bottom of the stairs on one knee, looking up at her. They continued their walk in the woods with the dogs happily engaged and spent the day with Jason's parents by the pool.