John Rolfe and Pocahontas
Pocahontas, a daughter of Virginia’s paramount native chief, Powhatan, became a pawn in a game of international strategy. She was married and had a child, but while visiting friends she was kidnapped and held captive in Henricus, where she underwent socio-religious indoctrination and was given a new name. Rolfe, a tobacco exporter, conflicted but attracted, married her in 1614. The two cultures were united and, for a brief time, peace kept between them. The Virginia Company arranged in 1617 to bring the Rolfes and a Powhatan delegation to England to show off “Rebecca,” the Christianized “savage,” as a living metaphor for conversion colonization. While in England, she contracted an illness for which she possessed no immunity and died.
Sydney and Frances Lewis
In Richmond, they were one-worded as SydneyandFrances. He started catalogue showroom business Best Products from scratch in 1958 and grew it into 200 stores in 27 states. During the 1960s, after physicians told Sydney he needed to find a nonwork outlet, he and Frances turned to their love of art and started collecting contemporary works. Best didn’t last into the era of big-box stores and liquidated in 1997. The couple later gave the Virginia Museum of Fine Arts 1,200 works by modern artists such as Jasper Johns and Andy Warhol, plus a huge collection of Art Nouveau and Art Deco objects and furnishings. To house them, the Lewises contributed to the museum’s $22 million, 90,000-square-foot West Wing. The museum’s Best Café is named in their honor.
Nicole Pries and Lindsey Oliver
On Oct. 6, 2014, the third anniversary of their commitment ceremony, Pries and Oliver followed a prompt that came by text from a friend: “Are you headed down to the courthouse to get married?” The U.S. Supreme Court had rejected a lower court’s decision to support Virginia’s prohibition of gay marriage. The two dashed to the John Marshall Courthouse under the afternoon sun to get ahead of what they thought would be a wave of marriages. And thus, Pries, then 42, and Oliver, 30, became Richmond’s first same-sex couple to marry.

Miles Berkley Jones and Sarah Garland Boyd Jones (Images courtesy Maggie Lena Walker Family Papers, Maggie L. Walker Historic Site)
Physicians Miles Berkley Jones and Sarah Garland Boyd Jones
Both Howard University medical graduates, the Joneses didn’t start out in the profession. They met teaching at Richmond’s Baker School and married in 1888. After the city barred African-American men from teaching public school, Miles first went into banking. After Sarah graduated from medical school in 1893 she opened Richmond Hospital at 406 E. Baker St. She became the first black female physician to pass the Virginia Board of Medicine and helped Miles through medical school. The couple was active in church and civic life in Jackson Ward and helped organize the Medical and Chirurgical Society of Richmond.
William Hunter ‘Bill’ Goodwin Jr. and Beverly Wilkes ‘Booty’ Armstrong
These two longtime business partners influenced the city and region’s development. Armstrong and Goodwin sold AMF Worldwide Bowling Centers in 1996 for $1.3 billion; with the proceeds they started several charitable foundations. Armstrong served with Richmond Renaissance and the Virginia Performing Arts Foundation that altered downtown with the Richmond Convention Center and what grew into Richmond CenterStage; he also led a $300 million modernization of the passenger terminal at Richmond International Airport, and was working on this project when he died in 2011. Goodwin, now retired, was a major force in creating an engineering school at Virginia Commonwealth University, and his Riverstone Group LLC bought multiple properties for development downtown and in Midlothian and Henrico.

Sallie May and James Dooley (Image courtesy Maymont Mansion Collection)
James and Sallie May Dooley
The Dooley estate of Maymont is testimony to the couple’s enduring affection for each other and their community. James made his fortune through railroads and real estate. In 1886 the couple purchased the dairy farm they transformed into Maymont, which included a mansion where they enjoyed hosting sumptuous affairs. Left as a gift to the people of Richmond after the death of the Dooleys, Maymont opened as a public park and museum in 1926. Though owned by the city, the 100-acre park is managed and maintained by the nonprofit Maymont Foundation. The Dooley tomb stands near their mansion.

Tiffany Jana and Matt Freeman (Photo courtesy Tiffany Jana)
Matt Freeman and Tiffany Jana
They co-founded TMI Consulting Inc., a diversity and inclusion management consulting firm, in 2010, the year before they married. Freeman and Jana have traveled throughout the country and overseas getting communities to speak constructively about the challenges in front of them. TMI has facilitated The Valentine’s Community Conversations about often hot-topic issues rooted in the city’s history. Jana, originally from El Paso, Texas, and in Richmond via New York City, met Freeman working with freelance facilitators in Northern Virginia. The two collaborated on a guide published in 2016, “Overcoming Bias: Building Authentic Relationships Across Differences.”
Mildred and Richard Loving
Traveling from their Virginia home to Washington, D.C., to be married by a minister they picked out of the phone book, the Lovings didn’t think much about the consequences of their 1958 union in a state where interracial marriages were forbidden. Mildred was not just African American but American Indian, Cherokee from her mother and Rappahannock from her father; there had been mixing for a long while in rural Caroline County. Richard, a brickmason, just wanted to establish a home for his wife and their children. Without meaning to, the Lovings became civil rights activists when the American Civil Liberties Union took up their case and in 1967 brought the issue before the U.S. Supreme Court. Earl Warren’s court ruled the miscegenation law unconstitutional. Their struggle inspired a compelling 2011 HBO documentary and a powerful 2016 film.
Raymond Harold Boone and Jean Patterson Boone
Ray Boone worked for various small newspapers and later as editor and vice-president of the Baltimore-based Afro-American newspaper chain. He taught journalism at Howard University and reported internationally for the National Newspaper Publishers Association, then founded Paradigm Communications, which in 1992 launched the Richmond Free Press. Wife Jean assisted in procuring the other lifeblood of newspapering besides ink: advertising. Ray openly criticized leaders, businesses and policies in the interest of the Free Press’ readers. In 2011, when Occupy Richmond protestors got booted from their Kanawha Plaza camp with the approval of then-Mayor Dwight Jones, Boone invited them to his yard — next door to Jones’. Ray died in 2014, and Jean, active in community affairs, became publisher of the Free Press.