The D'Alessandro Family: Overcoming Obstacles & Seizing Opportunities
Photo by Karen Presecan
The legendary basketball coach and teacher John Wooden once said, "Things turn out best for the people who make the best of the way things turn out." This quote encapsulates the essence of Diana D'Alessandro's journey, who turned an initial setback into the foundation for an extraordinary legal career. This resilience and determination have not only built her thriving solo practice but also her community here in Fredericksburg.
The D'Alessandro family— Diana, 40, Jon, 41, and their sons Jordan, 9, and Dylan, 5— moved to Fredericksburg from Fairfax in 2021, seeking something that had been missing from their Northern Virginia life. "I enjoy the small-town feel and sense of community— two things I never felt living in Fairfax County," Diana explains. "The people are noticeably different here— in the best ways possible."
Diana and Jon's story began when they were neighbors during Diana's sophomore year at Virginia Tech. "We met when I was 19, and he was 20— both of us attending school at Virginia Tech," Diana recalls. What started as a college friendship has grown into a partnership that spans careers, parenthood, and now their shared commitment to their new community.
Jon initially planned to become a medical doctor, majoring in biology, but his heart led him in a different direction. After two years, he decided to double-major in biology and biosystems engineering, graduating in 2008. His childhood summers at Lake Anna had sparked a love for water that would define his career path. Today, he's a licensed professional engineer with Kimley Horn, building their Virginia-wide stormwater practice as an expert in water resources engineering, stormwater management, and flood resilience.
Diana's journey to becoming a lawyer is a testament to perseverance in the face of adversity. Although she knew from a young age that she wanted to practice law, it was no easy feat. "I am admittedly a poor standardized test taker," she says, which became a challenge when she sat for the Law School Admission Test (LSAT). Diana was rejected from her top-choice law schools, but earned acceptance to a night program at Duquesne University’s School of Law. Instead of feeling sorry for herself, she packed her bags and set out for Pittsburgh, determined to prove herself.
“I knew I had to work harder to prove that, despite my LSAT score, I was capable of excelling,” she says. And “excel” she did. Working relentlessly, she finished her first year at Duquesne ranked 6 out of 84 students, earning several awards for her legal writing, research, and oral advocacy. This academic excellence proved to be more than enough for the University of Richmond to accept her into their full-time program the following year, where she graduated with her Juris Doctor in 2010.
Diana's achievements continued to build from there. She earned a prestigious judicial clerkship with the Honorable David S. Schell of the Fairfax Circuit Court—a coveted position granted to only 15 recent law graduates. She then spent nearly nine years at a boutique law firm in Tysons Corner, advancing from associate to partner and earning accolades for her outstanding work as a top attorney in her practice areas. In 2019, she was named an "Up & Coming Lawyer" by Virginia Lawyers Weekly, recognizing lawyers making an impact across the Commonwealth.
When the family decided to move to Fredericksburg in 2021, Diana discovered an underserved market and saw another opportunity. "When I began searching for attorney positions in the area, I realized that there are not many lawyers who specialize in my practice areas," she says. "I thought, well, if they can do it, maybe I can too." Her instinct proved correct—since accepting her first client in July 2021, her practice has grown at a rapid pace, helping hundreds of clients each year in litigation, estate planning, estate administration, and transactional real estate.
The D'Alessandro boys have inherited their parents' passion and determination. Jordan, 9, is a sports enthusiast who "loves soccer, basketball, and football" and is "an avid football-card collector" who can tell you "anything and everything you would ever want to know about football." His favorite team is the Miami Dolphins—not for any family connection, but because it was the first team he learned about, and he thought dolphins were "cool."
Dylan, 5, is following in his brother's athletic footsteps, having just completed his first season of tee ball and looking forward to starting soccer in the fall. He's equally excited about starting kindergarten at the same school as Jordan.
The D'Alessandro family has fully embraced Fredericksburg's community spirit in multiple ways. Diana volunteers regularly at her sons' elementary school and will join the PTA board in the fall. Jon coaches soccer for Spotsylvania County Parks & Recreation, working with Jordan's team and preparing to coach Dylan's team as well.
Their weekends often find them in downtown Fredericksburg, where Diana and Jon enjoy coffee at Anita's Cafe or wine at Curio. But their most frequent destination is The Card Cellar, where Jon experiences a full-circle moment. "It is a full circle moment for my husband, who would visit The Card Cellar at its previous location when he was our older son's age," Diana notes.
The D'Alessandro family's creative side is evident in their personal interests. Diana, in particular, is a talented baker. When friends and family learned she was opening her own business, many assumed it would be a bakery rather than a law practice. She recently organized a neighborhood bake sale for her son and his friends, contributing dozens of decorated cookies and treats. "It was not your average bake sale, and it was a big hit!" she says.
The D'Alessandro household is bustling with activity, thanks to their expanding pet family. Two rescued cats, Lovey and Meridian, were adopted through the Squishy Face Crew rescue organization. A year ago, they added Labrador retriever puppies Biscuit and Zoe, siblings who have brought yet "another layer of love and craziness" to the family.
As the D'Alessandro family settles deeper into Fredericksburg life, they're building the kind of community connections that initially drew them to the area. From Jon's hometown roots to Diana's growing legal practice, from youth sports coaching to school volunteering, they're creating the small-town experience they sought when they left Northern Virginia.
"I have no regrets about moving here," Diana shares, a sentiment that not only summarizes their successful transition but also their commitment to "making the best" out of every opportunity for them here in Fredericksburg.
