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Kaleigh Dolan

and

Drew Jaffe

September 6, 2026

Crested Butte, CO
81 days81 d18 hours18 h15 minutes15 min6 seconds6 s

Our Story

First comes camp, then comes marriage.

Some people meet once and just know. Drew and Kaleigh met a hundred times before they ever realized what they were becoming. Drew and Kaleigh first met in sixth grade at Camp Echo. At the time, it was simply summer—days by the water, nights around campfires, and friendships that felt endless. They were part of the same camp world, crossing paths again and again over the next ten summers. As campers they were friendly faces; as staff members they became friends. Each summer brought familiar laughter, shared stories, and the comfort of returning to the same place and people. During the school year they stayed loosely in touch, but camp was always the constant that brought them back together. Drew made no secret of his feelings even then—often telling Kaleigh he was in love with her—though she never thought much of it, since he said it to just about everyone. Life eventually took them in different directions. Kaleigh went to work in Nashville and Drew worked, traveled, and built his life in Chicago. Everything changed when Kaleigh came home from Nashville for spring break and Drew asked her out on their first real date. They talked for hours—about Drew’s recent trip to Asia, work, school, and life—and Kaleigh remembers laughing so hard her stomach hurt when she got back into the car. After years of country-boy dates in Nashville that never made it to date number two, she knew this one felt different. This was it. Just six days later, COVID-19 shut the world down. Kaleigh found herself back home with her family, just fifteen minutes from Drew’s house. Along with their camp friends, daily walks became routine, often stretching from one hour to two, always justified by taking the dogs out. Kobe and Piper (RIP), despite not being especially fond of other dogs, bravely tolerated each other for the sake of Drew and Kaleigh. Those months became the foundation of their relationship. With nowhere to rush to, they spent their time walking, talking, and getting to know each other deeply. They got to know each others families too—brought together by long card games at the Dolan dinner table, competitive Catan at the Levin's, and weekends at the Jaffe-Yingling lake house. Eventually, Kaleigh returned to Nashville and the couple spent a year navigating long distance. When she moved back to Chicago, she bought an apartment, and Drew—unexpectedly handy—took charge of fixing it up. Together, they turned it into a home. Today, Drew and Kaleigh live together in their cozy Uptown condo and are excited to get married. Along the way, they’ve shared unforgettable adventures traveling and eating their way around the world, including an Alaskan and Icelandic road trip, scuba diving in the Maldives, Palau, Australia, and Japan, and touring Florence, Kyoto, Doha, and Mexico City just to name a few of their favorites. A few moments from those travels can be found on the gallery page. What began as a decade of shared summers quietly grew into something lasting—and now they can’t wait to celebrate the next chapter with the people they love most.

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