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October 31, 2025
Madison, OH

Olivia & William

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Olivia Dottore

and

William Levand

October 31, 2025

Madison, OH

August 23rd, 2024 Olivia and Will’s Engagement in Steamboat Springs, Colorado.

High School Sweethearts? Sort of….

High School, a Cup of Coffee, and Our Forever

We met in high school, and for the first semester, we weren’t really on each other’s radars. But second semester of freshman year, we were seated next to each other in U.S. World History and our friendship grew as we discussed the amount of Altoid mints our teacher would eat throughout the class. We then were placed in the same geometry class, where we started to talk more and frequently joke with one another, along with other classmates. Toward the end of freshman year, our conversations left the classroom and carried on over text at home. We talked on and off throughout the summer and I (Liv) frequently thought what it would be like to be dating Will. Although we didn’t hang out once that summer, we talked consistently throughout all three months. Sophomore year began, I (Liv) remember sitting in the back of the car on the way to school, my heart was racing with anxiety about seeing Will. I, of course, played it very cool with an “oh hey” the first time I saw him that day, and walked away. We continued to talk despite me playing hard to get for months. Eventually, we went to homecoming together and began to date. We had dated for two years, broke up and went our separate ways. Fast forward seven years… After years of holiday, birthday, and random “hey” texts, I asked Will to get drinks or a coffee when I was in town from Colorado for Christmas. Will stupidly choose to get coffee. We ended up talking for two and a half hours before hugging and saying goodbye with no plans of seeing each other again. Of course, our text and phone conversations continued on after this coffee date. A few weeks later, Will mentioned he was headed to Colorado to ski. Conveniently having a very long layover in Denver, I picked him up from the airport and we traveled around Colorado for the next 24 hours. Will left and our relationship continued over text and phone calls for the next four months until I moved home. In May of 2022, I moved back to Cleveland. We went on our first date, and became an official couple (for the second time). We have been together ever since then, have had countless adventures, moved states, moved in together, got new jobs, and got engaged (clearly). We are excited to be getting married and continuing our story with each other forever.

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