Technically speaking we met on Match.com, however it was Courtney's ski house friends who were managing her online profile while on a ski trip in Telluride. Unbeknownst to Jim, they were the ones who did all the initial communicating and told Courtney she had a date on Tues, Wed, and Thurs the week she was back in Denver. Tuesday's date was with Jim, so Courtney was frantically re-reading the conversation and date plans that her friends had already arranged. Courtney, Jim, and Beatrice (Courtney's dog) met for an afternoon hike at South Table Mountain. Dusk was approaching so Jim scrambled to find a shortcut back to their cars, meanwhile Courtney sent Jim's profile picture to all her friends so they would know who to target if anything happened to her. By the end of the evening Courtney had cancelled her dates on Wed and Thurs.

Jim's surprise engagement plans went through multiple iterations given unpredictable Colorado weather. The day started with neighborhood excitement of a moose sighting. Jim asked Courtney to join him and the dogs on a scouting hike around sunset. The fact he invited dogs was a sign to Courtney he was not going to propose (because Jim hates hiking with the dogs). Right before they left for the hike the moose was in their yard and Jim was beyond excited! After a few miles Jim asked Courtney to sit for a moment to allow the dogs to rest. Before Courtney knew it Jim was down on one knee proposing! Courtney thinks she said "yes" and then spotted another hiker on the trailer. The hiker got closer and Courtney recognized the hiker was her friend Josh who was hired by Jim to take surprise engagement photos! Jim also planned a surprise celebration with friends back at the house.