Contents
If there are two things to know about Bill de Blasio, they’re: (a) He is the former mayor of New York City, and (b) his romantic life is sheer chaos. Ever since he and his wife announced their separation in the New York Times, this freakishly tall man has been deep in his Carrie Bradshaw era, dating up a storm and leaving at least a couple scorned exes in his wake. Have the single women of New York not been through enough without the city’s former mayor wreaking havoc on their hearts?
To make sense of it all, let’s discuss every woman de Blasio has married, dated, and smooched on his ruthless quest for true love.
Chirlane McCray
McCray and de Blasio met in 1991 while they were both working for then-Mayor David Dinkins. At the time, McCray very publicly identified as a lesbian, but she and de Blasio fell in love. They got married in 1994 and had two children together. In 2013, McCray told Essence — the same publication that published her 1979 essay titled “I Am a Lesbian” — what it was like to catch feelings for a man. “I thought, Whoa, what is this? But I also didn’t think, Oh, now I’m attracted to men,” she recalled. “I was attracted to Bill. He felt like the perfect person for me.”
Well, he was — for a while. In July 2023, McCray and de Blasio announced they were separating in a joint New York Times interview, as one does. They said they were not, however, planning on getting divorced, and explained that they would date other people while still living together in their Park Slope townhouse. “One of the things we’re saying to the world is we don’t need to possess each other,” de Blasio told the Times, sounding every bit the ethically nonmonogamous Brooklynite. De Blasio also asked if the Times would include a photo of him at the gym.
Mystery Woman No. 1
In September 2023, de Blasio’s reign of terror on the New York dating scene began. Two months after telling the Times he and McCray were effectively opening up their relationship, de Blasio was spotted making out with an unidentified woman at the Empire Rooftop bar. Photos published by the New York Post — which dubbed him “Bill de Smoochio” — showed them cuddling on a couch, and a tipster said they spent a good three hours in a heated lip-lock.
Not much is known about this woman, but someone at the bar told the Post she appeared “age appropriate.” Good for him. Apparently, that wasn’t their first meeting — a server said they’d been coming to the bar “at least three times a week.”
Mystery Woman No. 2
De Blasio and his Empire Rooftop fling seemingly didn’t last long — a month later, in October 2023, he was spotted with a different paramour. The two shared a romantic candlelit dinner at La Mercerie in Soho, per the Post. Again, not much is known about this woman, who perhaps wisely concealed her face with a black baseball cap throughout the meal. He reportedly sent her off to the subway at the end of the night with a peck on the cheek. Could he not have called her an Uber?
Kristy Stark
Things got messier for Bill de Bradshaw in December 2023, when he was seen walking through Noho holding hands with another woman. The Post identified her as Kristy Stark, the founder and CEO of Michigan-based literacy company MindsEmerge. It’s not clear how the two first met, but the company website listed de Blasio as one of its “experts & advisors.”
Click here to preview your posts with PRO themes ››
Further complicating matters, shortly after the story came out, her husband told the Post they’d been married for 12 years and had two kids together. Apparently, Stark’s claim that they were “in the process of getting a divorce” was news to her husband. “I don’t know anything about my wife holding hands with Bill de Blasio,” he told the paper, a sentence you really don’t ever want to find yourself saying.
Nomiki Konst
Fast-forward to February 2025; it seemed like de Blasio had moved on from Stark and finally found the love of his life. A day before Valentine’s Day, he announced he was in a relationship with Nomiki Konst, a political analyst and former Young Turks reporter 22 years his junior. He told the Post they had “known each other for a long time and are very kindred souls.” “We caught up over lunch one day and before it was over I told her I wanted to ask her out and she said very sweetly: ‘And I will say yes,’” the former mayor said.
The two were together for ten months, during which time they went on a romantic getaway to Greece, posed for a lot of selfies together, and wore matching “Hot girls for Zohran” tees at a No Kings rally. On November 4, de Blasio and Konst showed up at Mamdani’s Election Night victory party side by side. It was the last time they would be seen together in public.
Less than a week later, on November 9, the Post reported that the couple had broken up after de Blasio allegedly cheated on Konst with an unidentified “out-of-state elected official.” Per “Page Six,” de Blasio confessed to having an affair while he and Konst were on their trip to Greece. They apparently tried to patch things up, but while walking into the Election Night party, “Page Six” claims, Konst found out he and the official were still talking and that she planned on returning to New York to visit him. Shortly after the “Page Six” report came out, Konst appeared on a YouTube show called Why Did They Break Up? (her episode was titled “The Mayor Cheated on Me”), where she shared that she’d been freezing her eggs before she found out about the affair, and she and de Blasio had discussed having kids together.
Roxanna Valenzuela
View this post on Instagram
So, who was the mysterious “out-of-state elected official” with whom de Blasio had this alleged affair? Turns out, it was … another mayor. On November 11, the Post reported that de Blasio had cheated on Konst with Roxanna Valenzuela, mayor of South Tucson. They first met during a business lunch in September, per “Page Six,” and it sounds like things heated up pretty quickly — the two allegedly went back to de Blasio’s place after lunch to hook up. Two days later, Valenzuela reportedly took him to volunteer at a soup kitchen, where “tins of split pea soup weren’t the only cans Hizzoner got his hands on,” as “Page Six” so eloquently put it.
De Blasio, never one to miss out on a tabloid exclusive, confirmed to “Page Six” he’s now in an amazing relationship with Valenzuela. He told the paper he wishes Konst “well” and is “sorry” for how their relationship ended. “I fell in love with someone else and I should have told her sooner,” he said. “I’m now in a wonderful relationship with Roxanna Valenzuela that we will continue to nurture and keep private.” So far, it seems like it’s going pretty well — Valenzuela already hard-launched him on her Instagram, sharing a photo of them with Arizona representative Adelita Grijalva at her swearing-in ceremony in Tucson on December 6.
