For much of their relationship, Isaac repeatedly told Kayleigh that he would need to go to Wisconsin with his dad to pick out a ring, since his dad used to work at a jewelry store out there. Then one weekend in November 2024, Isaac said he was going to Wisconsin with his dad to pick up a car. Naturally, Kayleigh became suspicious that they might also visit a jewelry store on their trip. She was right.

However, Isaac was determined to throw her off the scent. So, he strategically told her roommate (Anika) that he did not get a ring, but instead purchased "I'm-sorry-I-haven't-proposed-yet earrings," which he gifted to her the night before he popped the question.

The morning of 12/21, Isaac insisted that they stop at the Zollman Zoo outside of Rochester on the way down to Iowa for Christmas with Kayleigh's family. Kayleigh didn't understand why she couldn't sleep in and had to get up to go to a tiny zoo, but she agreed anyway.

They arrived at the zoo for it's 10am opening, and one other person happened to also be there, which Kayleigh thought was weird but ultimately wrote off as a coincidence. They meandered around the nature center for a bit and then headed outside to see the animals. Kayleigh wanted to go see the otters, but Isaac was oddly determined to get to the bison right away. When they got to the bison, Isaac suggested taking a selfie, which was the cue for the other gal that was at the zoo to offer to take a better photo of them. (As it turns out, she was the fiancée of a friend of Isaac's that Kayleigh had never met before.) Before Kayleigh knew it, Isaac was down on one knee asking her to marry him!

Registry