Sydney woke up and told Jon that she had a dream about him proposing. She suggested they get brunch at the restaurant where they had their first date, Sips and Such.

For the first time in his life, Jon is hurrying Sydney to get ready because he had made a dinner reservation before they were to see Hamilton in Playhouse Square. They have a lovely dinner at District where Sydney has too many martinis. They decide to take a picture in front of the light-up ornament to remember the night. Unbeknownst to Sydney, Jon had already planned this but he let her think the picture was her idea.

Jon gets down on one knee! He said "You know I love you and will love you forever." She said "Yeah, I love you too," while trying to scope out a good photo spot. When she turned around Jon was on one knee and asked. Sydney didn't even say words because she had no air in her lungs, just nodded yes then kissed him. Jon's sister and brother-in-law had been hiding recording and taking pictures of the interaction (thanks again guys!).

Jon and Sydney went to Hamilton. Sydney doesn't remember most of it because she couldn't stop crying and staring at the ring Jon had designed for her. They started wedding planning immediately!