Matt & Anna are from the same church and Anna started going to Matt's community group. All the guys planned a special event for the girls for International Women's Day (March 8th). Each guy was paired with a girl and had to pick them up from their house and drive them to the party (like a prom date). Anna lived the farthest away and Matt had to go pick her up. On their long drive, they got talking and became comfortable with each other. Some time after, in 2017, they went to a Leadership Conference called Thrive at Bayside Church. After the conference Matt asked Anna to be in a relationship with him and she said yes. They dated for a whole year. The next year they went to Thrive Conference in 2018, Matt coordinated with the staff beforehand to have Anna and Matt come on stage and participate in a game. They ended up winning and Matt grabbed the mic to say a few words and while being super nervous, he managed to get on one knee and pop the question in front of thousands of viewers in the audience and live stream online. The crowd and staff went wild with applause and cheering.