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Middleburg Meet Cutes

Middleburg Meet Cutes

Written by Kaitlin Hill

Middleburg’s cobblestone streets, cozy corners, and welcoming community are all the ingredients of a Hallmark romance. It’s no wonder, then, that so many couples find love here (or nearby), and enjoy long, meaningful relationships. In the spirit of Valentine’s Day, we asked four local couples how Middleburg has played a role or acted as a backdrop for their love story, their secrets to happiness, and if they had any advice for budding lovebirds. 

Michelle and Chris outside of the new Middleburg Town Hall. Photo by Callie Broaddus.

Michelle & Chris

Both locals, Michelle and Chris met working together for a locally-owned Middleburg business. Chris explains, “We kind of bonded over late nights doing lou lou inventories in D.C. How we got to know each other so well was driving back and forth from D.C.” Their Hunt Country to D.C. commute set the foundation of a strong friendship which quickly blossomed into a relationship that would flourish in Middleburg. “We moved here during that crazy snowstorm in 2016,” Chris explains with Michelle adding, “In the lou lou moving van!” The two would go on to have their son Maverick and later open The PLAYroom in downtown Middleburg. Michelle spends her days in town operating the family business, while Chris splits time between his real estate work and serving on the Middleburg Town Council, most recently as vice mayor. When asked how Middleburg has played a role in their romance, Chris jokes, “As the most significant third wheel ever.” Michelle adds, “We love community and we were so excited to build a community together. And I think this is such a cool place to do that. Everyone kind of took care of us and fostered us while we were first starting. And now we’re at this point in our life where we can kind of give back and still be part of the community.” Chris expands, “It’s been a very welcoming place. It’s a unicorn small town like Mayberry.” Michelle finishes, “We always say that.” 

When asked what makes their relationship so solid, Michelle says, “Being together makes us independently better. So many of the things that we’ve done are independent goals. I’ve reached my independent goals. He’s reached so many independent goals for himself, but we’ve been able to do it together.” Chris adds, “We’re a very good team. We bring out the best in each other most of the time. And,” he finishes with a laugh, “we’re just like BFFs. I would rather do anything with Michelle than with anyone else.” 

Isabella and Alexander at the PEC Ball last fall. Photo courtesy of Isabella Wolf.

Isabella & Alexander

For Isabella and Alexander, it seems fate might have played a role in their meeting in Marshall. Isabella shares, “I brought a fellow realtor to a property to get their opinion on a house before putting it on the market. It was still being renovated but close to being done, so when we got there, we crossed paths with the general contractor, who happened to be Alexander. I don’t even remember what was said but we just hit it off and kept chatting, so much so that even the realtor I’d brought along gave me a look that seemed to say, ‘I think he likes you.’ That day I went home and told my best friend that I thought I just met the man I’m supposed to be with.” To add even more romance to their meeting, “We met at the house on Swain Mountain outside of Marshall, looking out over an incredible view. Swain means ‘a lover’ or ‘a suitor,’ so it literally couldn’t have been more perfect.” 

At the end of 2023, the couple got engaged. “The day after Christmas, I came downstairs thinking we were going to a brewery when I noticed a trail of flowers and candles leading to the Christmas tree. I followed the path to see him there, and it slowly dawned on me what was happening. Both of us were speechless as he knelt down on one knee, and I was beyond words but managed to squeak out a ‘yes’ before the happy tears started.” When asked what they are looking forward to in the future, Isabella shares, “Enjoying making a home together, adventures together, and continuing to cheer each other on in our respective careers.” And advice for other couples? “Be each other’s cheerleader in things important to that person. Value the couple and also the individual pursuits of each other.” 

Nancy and Billy about to set out for a hunt. Photo courtesy of Tiffany Dillon Keen.

Nancy & Billy

“I’ve known him all my life,”  Nancy explains of her husband Billy. She adds, “Let’s see, his father used to bring him out to the farm all the time, hunting and stuff. Tranquility Farm. Our mothers knew each other well.” Their mothers’ close friendship resulted in Nancy and Billy spending a lot of time together, which suited the mothers who, Nancy suspects, wanted them to end up together. “I guess they had their fingers crossed,” she laughs. And when it came time for marriage, Nancy remembers her father giving them a choice. “Dad said we could have the choice of a big wedding or land. Of course we picked land.” The couple settled in Philomont and opened a riding school there. Their wedding was on Nancy’s 24th birthday. Now 88, Nancy shares that her favorite thing about Billy is “his patience.” When asked what she thinks Billy’s favorite thing about her is, Nancy gets quiet, but her daughter Daphne shouts, “Her cooking!” Nancy laughs, “Well, he thinks my cooking is okay.” Though Nancy is hush-hush on what Billy loves about her, she has an endless list on what she loves about Billy. “He’s the best. He never complains or anything. He loved helping us with the horses.” She adds, “And he loves kids. We have four children and a lot of grandchildren. He named all the kids ‘Crumb Crunchers’ because they were always stealing cookies. He loves children.” She finishes, “He is pretty special.” 

Julien and Cassandra with one of their children. Photo courtesy of Julien Lacaze.

Julien & Cassandra

“The first time we met was in a job interview,” Cassandra explains about their initial interaction in 2016. “We met at Slater Run Vineyards. Julien was working there. He had already been there for a couple of years and I was recommended by a friend to apply to their assistant winemaker position. So, I did. And Julien was one of the people to interview me. I ended up taking the job, and we worked together for a year and a half, I think, before we started dating.” The couple, who have lived all over Hunt Country from Marshall to Paris to Warrenton and back to Marshall, says that Middleburg and Hunt Country have “definitely been part of the backdrop” of their relationship. As for their wedding? “We’re not very good with dates,” Cassandra laughs. Julien adds, “We don’t even agree on our wedding anniversary.” Cassandra finishes, “Every year we pick a day in September and say, we know it was around here.” 

When prompted to share their favorite qualities of each other, there is no hesitation. Julien jumps in, “Her ambition. I always get carried away with ideas and things that I want to do, and she always runs with me. And, we kind of conquer the world together. She’s my biggest supporter.” Cassandra has an answer ready, too: “Julien can be very calming and grounding and he is the backbone of our family. We’re both really lucky, but I feel very lucky to be able to raise a family with him here.” She continues, “He can handle anything. And he’s just a big calming force in my life and in our family.” That family now includes two little ones, which Julien and Cassandra are excited to raise in the area that they love. When asked for their advice for other couples, Julien says simply and sweetly, “Don’t wait.” ML

Published in the February 2024 issue of Middleburg Life.

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