Two decades earlier, she had been a prime focus of his investigation into then-President Bill Clinton and the commander-in-chief's claims about the nature of his relationship with her, a former White House intern.
It had been a long time, but she hadn't forgotten. How could she have?
And now - finally - Monica Lewinsky was standing face-to-face with the man who had helped upend her life.
"Let me introduce myself. I'm Ken Starr," Lewinsky recalls the former special prosecutor saying on Christmas Eve.
"This was the man who had turned my 24-year-old life into a living hell in his effort to investigate and prosecute President Bill Clinton on charges that would eventually include obstruction of justice and lying under oath - lying about having maintained a long-term extramarital relationship with me," she writes in Vanity Fair.
"Ken Starr asked me several times if I was 'doing O.K.' A stranger might have surmised from his tone that he had actually worried about me over the years."
She adds: "His demeanor, almost pastoral, was somewhere between avuncular and creepy. He kept touching my arm and elbow, which made me uncomfortable."
Asked Monday about the chance meeting with Lewinsky, Starr told The Washington Post only that "it was an entirely pleasant but poignant encounter on Christmas Eve" but declined further comment.
A spokeswoman for Lewinsky declined to comment.
In a pointed essay about what she learned from #MeToo movement, Lewinsky writes about the moment she bumped into Starr - the "man in the hat," as she calls the former U.S. Solicitor General and federal judge - over the holidays at a restaurant in New York.
"I turned and introduced him to my family," she writes. "Bizarre as it may sound, I felt determined, then and there, to remind him that, 20 years before, he and his team of prosecutors hadn't hounded and terrorized just me but also my family - threatening to prosecute my mom (if she didn't disclose the private confidences I had shared with her), hinting that they would investigate my dad's medical practice, and even deposing my aunt, with whom I was eating dinner that night. And all because the Man in the Hat, standing in front of me, had decided that a frightened young woman could be useful in his larger case against the president of the United States."
Lewinsky wrote about her years-in-the-making encounter with Starr in her Vanity Fair essay, "Monica Lewinsky: Emerging from 'The House of Gaslight' in the age of #MeToo."
Now, 20 years after the Starr investigation thrust Lewinsky into the national spotlight, she says the women (and men) now speaking out about sexual harassment and abuse have given her a "new lens" to see her own story.
"Given my PTSD and my understanding of trauma, it's very likely that my thinking would not necessarily be changing at this time had it not been for the #MeToo movement - not only because of the new lens it has provided but also because of how it has offered new avenues toward the safety that comes from solidarity," she writes.
Lewinsky explains how less than four years earlier, she had written in Vanity Fair that any "abuse" she endured from her relationship with the president "came in the aftermath, when I was made a scapegoat in order to protect his powerful position."
"I now see how problematic it was that the two of us even got to a place where there was a question of consent," she says now. "Instead, the road that led there was littered with inappropriate abuse of authority, station, and privilege. (Full stop.)
"Now, at 44, I'm beginning (just beginning) to consider the implications of the power differentials that were so vast between a president and a White House intern."
Lewinsky says that she has learned much since 1998.
Writing about her Christmas Eve run-in with Starr, she says: "The next month would mark the 20th anniversary of the Starr investigation expanding to include me. The 20th anniversary of my name becoming public for the first time. And the 20th anniversary of an annus horribilis that would almost end Clinton's presidency, consume the nation's attention, and alter the course of my life.
"If I have learned anything since then, it is that you cannot run away from who you are or from how you've been shaped by your experiences. Instead, you must integrate your past and present."