Isaac and Kailey dated briefly at the start of sophmore year of high school. Then, junior year Kailey asked Isaac to prom. They kept things casual, and talked for a few months before Isaac asked Kailey to dance for the last song of the night at senior year homecoming. He made it official and asked Kailey to be his girlfriend a few weeks later.

After high school they started long distance when Kailey went to UW Milwaukee and Isaac went to UW Madison. Kailey tranferred to UW Madison sophmore year and they got to spend a lot more time together. Senior year they got their own apartment and adopted a kitten, Lilo.

After college graduation, they went back to doing long distance when Isaac moved for a job and Kailey moved back home for her job. Isaac eventually moved back home and shortly after they got an apartment together again. From there, they got a puppy, Moose, and realized they needed more space. They bought a house together in the summer of 2022.

Isaac and Kailey went back to Madison for a weekend away, to do some of the activities they loved to do while going to school there. They went to a hockey game, a basketball game, and enjoyed some of their favorite restaurants. Isaac had planned on proposing at Kailey's favorite little restaurant off of State Street, but the restaurant was so busy, his plan fell apart. He ended up finally proposing back at the hotel after dinner.

Since the proposal, they have added a golden retriever, Winnie, to the family as well.

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