Ryan met Jeff Wulbrun (Kendall's dad) in the spring of 2016. Ryan was a student manager with the Stanford men's basketball team, and Jeff was a new assistant coach. Over the next few months, Ryan and Jeff spent countless hours together in the gym and even traveled to China together for the first game of the season. The Wulbruns moved to California 10 days before Kendall left for her freshman year of college at TCU, so she didn't have a chance to meet the team until she was home for winter break that year. Ryan didn't even know Coach Wulbrun had a daughter until December. At one of the basketball games while she was home, her mom and grandma (they like to take all the credit) pointed Ryan out to Kendall. She shrugged off the idea of her mom and grandma trying to set her up with someone they barely knew (although her mom insists her intention was for Kendall to find a friend since she didn't know anyone in the Bay Area), but she did think he was cute. Sometime that week, Kendall followed Ryan on Instagram and proceeded to stalk the five pictures he had posted (continually looking at one of him from the trip to China where he looked especially cute). He followed back and did the same, but noticed she had followed other players so didn't think much of it. A few days later, Kendall and her mom traveled to LA with the basketball team for the USC and UCLA games. Ryan and Kendall had their eyes on each other for most of the trip and finally had their first conversation leaving dinner at a former player's house. Kendall was watching Coach Pruitt's daughter who wanted to sit in the back of the bus with a player. Ryan overheard the conversation and intentionally sat in front of said player on the bus. The whole way back to the hotel the four of them played "the princess game" together, but they didn't have a chance to really talk with each other. Fate intervened in the form of a long wait at baggage claim after their flight home, giving them time to get to know a bit about each other. Kendall was disappointed Ryan didn't ask for her number. He was interested but knew she was headed back to Texas for school (plus, she was his boss' daughter). But Kendall couldn't stop thinking about him, so a few days later, she messaged him on Facebook (even though she thought that was awkward) telling him how great it was to meet him and she hoped they could hangout the next time she was home. Ryan insists he thought her message was a clear ploy to get his number and willingly supplied it in his first response. They texted almost constantly for eight weeks before Kendall came home again for spring break. They kept their interest in each other a secret for a while, but Kendall's parents eventually found out, leading Coach Wulbrun to tell Ryan that he "thought it was cool" Ryan was talking to his daughter one day at practice. Kendall and Ryan hung out each day while she was home for spring break and officially started dating on March 16, 2017 after dinner at Five Guys, the new Beauty and the Beast movie in theaters (including their first kiss at the end of the movie), and sitting on the roof of the car at a vista point nearby (not far from where they'll get married). They both posted a picture on Instagram after they started dating, and Ryan immediately got multiple calls from basketball players freaking out he was dating the coach's daughter. The players (and coaches) had a lot of fun making jokes about his "father-in-law" over the next couple of years. Turns out they were right! They did long distance for over two years between California and Texas. Ryan visited Kendall in September before he started school and again in March for spring break after basketball season ended. Kendall made trips home over school breaks and summers (and several additional weekends). After graduating from college, they traveled through Europe for 2.5 weeks then moved into their first apartment together in Menlo Park.

Ryan and Kendall knew pretty early in their relationship they wanted to get married, but they wanted to live together first and experience life together outside college before diving into marriage. As they moved to Colorado in the summer of 2021, conversations about an engagement became more frequent. Kendall played a big role in picking out her ring, but she didn't know when Ryan would decide to propose. With some help from Kendall's best friends Meghan and Elyse (who did a great job keeping it a secret), Ryan had been plotting some ideas for a while. On chilly fall walks near their apartment, Kendall and Ryan would talk about how he would pop the question, with Ryan usually joking about ways he wouldn't seriously consider just to mess with her. Kendall had established two rules (Ryan claims there were more than two): she wanted to look nice and she wanted someone to take pictures when it happened. During the pandemic, occasions where they dressed up were few and far between, but an opportunity finally presented itself in December of 2021. For Christmas and New Year's, they traveled back to California to celebrate with Ryan's family, including a trip to the beach in between the two holidays. Ryan's family had planned to take family pictures by the water for a late Christmas card. Kendall suspected that might be a good time for Ryan to propose, so she was careful never to suggest it as an idea during their conversations (so as not to spoil the surprise if it was what he had planned). She was so suspicious she took a close look at his pockets as they headed out to the beach for pictures (because Ryan had once asked how to hide the box in his pocket). When she didn't notice anything, she figured it wasn't going to happen. After taking group pictures, Ryan asked his sister to take some of just him and Kendall (because he knew Kendall was always game for cute pictures). As they finished, Kendall turned to head back to the beach house, thinking they were done. Ryan grabbed her hand, said he wanted to take one more, and got down on one knee. Neither one can remember what Ryan said before he popped the question, but it was the easiest YES for Kendall. Erin took beautiful pictures of the proposal, and Ryan's parents had already headed back to the house to set up decorations Kendall's mom sent for the occasion. Kendall's family had been in on the secret the whole time (Ryan had even shown the ring to Kendall's parents and brother in Colorado before they left for California). It was easily one of the best days of both of their lives and one they'll remember forever! An especially sweet moment was Kendall's realization that first night that she was going home with a fiancé, not a boyfriend!