Tyler and Ashlan met through their church, City on a Hill, in January of 2017. They remained friends and bonded through running, hiking, and being involved in the same group of people. After about 7 months of friendship, Tyler manned up and asked Ashlan on a date to which she said "sure." But it seemed to go okay because three weeks and multiple outings later they were officially dating.

On May 11, 2018, Ashlan thought she was headed into Boston to celebrate Meagan's (her roommate) graduation with a nice dinner. Little did she know, this was a coy to get her downtown without arising her suspicions. Months of planning and scheming led to the perfect surprise! Tyler got down on one knee along Fan Pier in the Seaport and asked her to marry him.


Afterward they enjoyed a nice (and somewhat rushed) dinner together because Tyler had a bit more up his sleeve for the evening. They headed to their next location which was Ashlan's house. Tyler and Meagan coordinated a surprise party with their friends to celebrate. When they arrived, they started to say hello to everyone and then Ashlan turned around and her mom and two sisters walked in! Tyler had asked them to travel to Boston for the big event! Another amazing surprise to an already perfect evening, followed by an impromptu weekend with family!