Jess and Charley met at a 7 a.m. indoor cycling class called Flywheel. Jess was the instructor. Charley was the rider. They wouldn't actually go on their first date for another three months, but during that time Charley took 28 of Jess's Flywheel classes, finding any excuse to talk to her before or after class. He would even Facebook message her to ask about songs she played in class. By the time he was showing up to classes in the middle of the work day, it became painfully obvious to everyone involved that he was genuinely interested in Jess, and he finally worked up the courage to ask her to grab Jamba Juice after a Sunday morning class.

Exactly four years later, Charley and Jess took their beagle, Bryzzo, for a walk to the Newport Harbor Lighthouse while vacationing in Newport, Rhode Island. After a brief interlude mid-speech for Bryzzo to go to the bathroom, Charley got down on one knee. Jess was so surprised by the proposal and the hidden photographer that it was a complete coincidence she was in full hair and makeup with freshly painted nails, a primary and secondary outfit from Rent the Runway, and white heels that had been shipped overnight to the hotel. It was a picture perfect moment, except for Charley opening the ring box upside down.