Bryan and Jaymie first met in 2023 after Jaymie moved to Pittsburgh. Both of them were working at Beemac Logistics at the time. For their first date, Bryan planned a romantic trip to The Point to show Jaymie the fountain for this first time. However, the fountain was still turned off for the season when they arrived - Bryan had to pivot his date plans in the moment. Despite the initial set back, the two had a perfect evening, and continued to see each other regularly outside of the office. Their first relationship milestone was May 11, 2023, when Bryan asked Jaymie to officially be his girlfriend. He took her to see Jersey Boys, and afterwards, he popped the question during a walk through the city. Fast forward two years to June 2025, Bryan orchestrated the ultimate full-circle moment. He brought Jaymie back to The Point—the place he took her on their first date. In an ironic twist of fate, the fountain was once again turned off! But just like the first time, it didn't matter. As "Can't Take My Eyes Off You" by Frankie Valli (from Jersey Boys) played, Bryan dropped to one knee and popped THE question - and Jaymie said yes!