The first time the couple met was when Rylie had her first interview at Airgas in Austin. Mark was working as an account manager at the time, and was called into the sales manager's office that day, not having a clue what was going on. It was in that office where the couple was first introduced to each other. Rylie accepted an account manager position shortly after, although the couple didn't re-connect until August 2021.

After a year of working together, Mark (finally) took the initiative and invited Rylie to join him and his buddy paddle boarding on Lady Bird Lake. Rylie and her girlfriends joined the guys on the lake, and that is where the couple's relationship began to take off. The conversation was easy and the laughter was never-ending. They discovered their shared love for Pinthouse pizza, Nickelback, college football, and tequila. A few months went by before Mark made it "official", and somehow proved that moving slow and steady does sometimes win you the race.

Mark had coordinated "plans" for him and Rylie to meet his mentor and his wife for dinner that Sunday night. Rylie showed up at Mark's house dressed and ready for what she thought was an Italian dinner. When Mark drove them through downtown Austin, he pulled off into the parking lot of Mattie's. Rylie was completely oblivious and was too distracted by her own story-telling to notice the detour. When the car came to a halt, Rylie looked around and quickly asked "What are we doing? Where are we?". Mark had their favorite song, Lady May, playing over the sound system, he grabbed her hand, and said "I have something to show you". He lead her through the empty parking lot, up the sidewalk, to the back pavilion of the restaurant. There was a trail of rose petals leading to a blanket setup with champagne, candles, the dainty ring box, and an engraved Bible that read Rylie McCulloch. Mark got down on one knee and Rylie said YES! A photographer captured the moment beautifully, and the couple celebrated with their families at Perry's Steakhouse following the proposal.