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July 6, 2025
Vail, CO
#LivLoveJacob

Olivia & Jacob

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Jacob Itskovich

and

Olivia Dworkin

#LivLoveJacob

July 6, 2025

Vail, CO
58 days58 d7 hours7 h22 minutes22 min27 seconds27 s

Our Love Story

Olivia and Jacob’s love story didn’t begin with a grand gesture but with two people crossing paths in dental school, both focused on their own futures. While they knew each other, it wasn’t until residency that something deeper blossomed. Their connection grew naturally, and before they knew it, they were close friends—laughing, supporting each other, and sharing dreams. Then one day, Olivia, being her bold and adventurous self, decided to shake things up by asking Jacob out on a date. They of course went to Dive Bar, and after that night, everything changed. What started as a simple date quickly turned into endless texts, laughter, and many more adventures. Jacob’s move back to Michigan didn’t stand in the way of their love. They stayed together through the long distance, met each other’s families, and made every moment together count. And then came March 18, 2024—the day that would forever be etched in their hearts. Olivia found herself in her favorite place on earth: the top of Blue Sky Basin at Belles Camp in Vail, Colorado. After an exhilarating and distracting ski run with Robbie, Olivia took Earle’s chairlift up to Belles Camp. As she skied past the BBQs and picnic tables, her heart skipped a beat. There, inside a heart made of rose petals, stood Jacob. Time seemed to stand still as he got down on one knee, the mountain peaks surrounding them, and asked the question she had dreamt of hearing. It was perfect in every way, and with tears in her eyes, she said yes to forever with him. They spent the rest of the day in custom t-shirts made by Robbie & Aviva—“He Asked” and “She Said Yes”—with skis on their feet and love in their hearts. Their celebration continued at the base of the mountain, where Alexis and Spenser helped bring the party to life with shot-skis, fries, and nachos at the iconic Red Lion, surrounded by family and friends, fresh snow, and the promise of endless adventures ahead.

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For all the days along the way
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