Haylee and Stewart met at a bar in Waco, TX when Haylee was a bartender and Stewart was a student at Baylor University. They met one night when Stewart came in with a group of friends that wanted to sit by the "Hot Bartender". It wasn't for another two years until they ran into each other again at a different bar that Haylee was working at. After working up the courage, Stewart got Haylee's number and they started seeing each other for 4 years until their engagement.

Stewart and Haylee were taking a trip for their 4-year anniversary to Jackson Hole, WY. It was a dream of Haylee's to visit! The night of the second day they were there, Stewart convinced Haylee to go out to the Black Tail Ponds with him before their dinner reservation. Stewart led Haylee out to a spot off the path where he asked a lady standing out there to take a photo of them. As Haylee reached back to the lady to get her phone back, Stewart went down on one knee and proposed to her! The lady taking the photos happened to be their photographer and pulled out her camera and captured the proposal. It was seconds later when 2 couples started cheering in the background and started running towards them. Stewart had secretly invited Haylee's friends and their husbands to surprise her that night. Funny enough, those couples had arrived in Jackson a day before Stewart and Haylee and had to dodge them repeatedly for them not to give away the surprise.