Ryan reconnected with Hailey's friend Jordan on Instagram. They had known each other previously through a Christian camp they had both attended. Ryan and Jordan ended up going on a date with one another, but Jordan knew they were not compatible with one another. She ended up giving Ryan Hailey's phone number. Following this date, Hailey was helping Jordan was getting ready for another date and Jordan continued to show Hailey Ryan's picture hoping she would be interested. Hailey was not interested in dating at the time. A couple weeks later, during the middle of Hailey's evening audiology class, she got a text from Ryan. They texted back and forth for a couple days before he ended up asking her out and they went out that Friday. Their date was all set for Friday evening and they had decided on a coffee date. As their date was late in the evening the only coffee shop opened at that time was Starbucks. They simply decided they would meet up at Starbucks in Centerra. Little did they know, there were two Starbucks in the Centerra area. They ended up showing up to different locations. When Hailey walked in, the Starbucks location was crowded and not a single young man was present in the coffee shop. They ended up realizing they were at two different locations. Since the Starbucks Ryan was at was empty, Hailey ended up driving to Ryan's location. When Hailey walked in to the second Starbucks that night, no one was in sight. Ryan had ended up going to the bathroom the exact moment she had shown up. After all the craziness of trying to meet up, they finally met for the first time. The date ended up going really well and they scheduled a second date. Unfortunately their second date ended up being cancelled due to a global pandemic. However, they liked one another enough that they ended up finding a way to make a relationship grow amidst a pandemic.

As Hailey's time in grad school was nearing an end, Ryan knew he was ready to propose. Hailey had been hinting pretty hard that she was ready to get engaged, but Ryan already had plans in motion. Ryan would not let Hailey tell him anything about the rings she liked as he thought she would then know she was in the engagement window. Ryan wanted two things: to pick out the ring with his mom, and to completely surprise Hailey with the proposal. Ryan knew that a ring Hailey would like would have a silver band with a round stone. Ryan began ring shopping in April 2023. Although Ryan had several ideas on where and how to propose, in May 2023 he ended up deciding to propose at Denver Botanical Gardens. He knew that when he proposed Hailey would want to look nice, so that ruled out proposing on a hike. Since Hailey's schedule fills up so quickly and she plans so far in advance, Ryan unfortunately knew that he had to schedule himself into her calendar for July 8th. Ryan knew that scheduling himself into her calendar would look suspicious and raise some questions, so he began throwing Hailey off by talking about a pretend trip to Colorado Springs in September that would be "really special and a great time". Hailey fell for this trick and began telling people she was getting engaged in September anytime someone asked. Ryan bought the engagement ring June 4. He had a 30-day return policy on the ring just in case Hailey didn't like it. But he was all set to propose on July 8 which was 4 days past the return date, so Hailey better like the engagement ring. Ryan knew he needed photos of the big proposal, but sneaking a photographer into the Botanical Gardens was tricky and difficult to do. On June 23, Ryan texted his cousin Katie asking her if she and her boyfriend Stone could be there to take photos. He then framed this as a double date which the two couples have been talking about during many family get togethers. On June 26 Ryan called Hailey's dad John. Ryan had never called Hailey's dad before and Ryan began the conversation by telling John how much he loved his daughter. The moment John got the call from Ryan, he went running through the house to find Hailey's mom Desiree, who happened to be home that day, as he knew this is the call they had been waiting for. John put Ryan on speaker phone so both him and Desiree could hear the call as Ryan asked for Hailey's hand in marriage. They gave Ryan their blessing to propose. As the proposal staged as a double date grew closer, Ryan was very nonchalant with the plans of the day while he continued to talk up Colorado Springs. Ryan kept saying that he wasn't too sure of the plans for the day and thought that maybe we could do a picnic and go to the Botanical Gardens that day. Ryan continued to say he would see what Katie and Stone wanted to do, even though Ryan was planning the day all along. Throughout their relationship, Ryan and Hailey went on many picnics and have a couple each year. Additionally, Ryan and Hailey hadn't been to the Botanical Gardens since their first year of dating.

On the day of the engagement, Ryan and Hailey met Katie and Stone for a picnic. Ryan decided on a picnic because they have gone on many picnics throughout the years. Following the picnic, the group headed over to the Denver Botanical Gardens. Ryan had three spots in mind for where he was going to propose and figured whichever spot they got to first would be the location where he would propose. Throughout their time at the Botanical Gardens, Katie kept wondering where Ryan had hidden the ring. Since Ryan knew that Hailey often stored her phone in his pockets, he knew he couldn't carry the ring in an easy to find place. Ryan was hiding the ring in the tiny front pocket of his jeans, without the box. All day he continued to feel his pocket to make sure he still had the ring. Ryan knew he needed to give Katie and Stone a signal before he was about to propose; however, he couldn't seem to shake Hailey by his side all day. Finally, Katie and Hailey wondered off to look at some bonsai trees. Ryan told Stone that his signal that he was about to propose was him scratching his butt. Finally, the couples came across the pond and Ryan gave his signal. As he got down on one knee, Hailey began to shake and could only say "hi" out of pure excitement. Ryan had forgotten the speech he had prepared due to excitement in the moment. Ryan asked Hailey to marry him and she said yes. Hailey had no idea that July 8th was going to be the day Ryan would propose. The first people Hailey called were her parents followed shortly by her sister Felicia. Felicia had no idea the engagement was happening and was completely shocked when she saw the ring. After the engagement and calling family, Ryan and Hailey took many photos around the Botanical Gardens and finished the evening with family at Burn Down restaurant. It was the perfect day!