Ashley and Corey met at Tia's in Boston, Massachusetts when they both happened to be out with their friends. Ashley recognized one of the guys Corey was out with as someone she had grown up with. The two groups started talking, and Ashley and Corey hit it off. While one of them may remember the night better than the other, the two formed an immediate connection and went on their first date a few days later.

After missing Thanksgiving with family last year due to COVID, Corey and Ashley had planned to make the trip to Hull, Massachusetts, to spend time with family and friends. On the day before Thanksgiving, Corey asked Ashley to take a walk before dinner. With the company of Corey's mother, Belinda, they walked down to a rocky area overlooking the ocean. While Belinda was taking their photo, Corey got down on one knee and asked Ashley to marry him. She, of course, said yes.