DC Power Players Are Paying Thousands of Dollars to Find Dates

The Requests

“Cuomo was seriously, hugely popular”

Woodward Pu can’t even tell me how many women have told her their number one crush is Andrew Cuomo.

“During the pandemic, SO many people were like, I just love Andrew Cuomo,” she said. This was in Covid’s early days — before Cuomo resigned as governor of New York, facing likely impeachment, over 11 allegations of sexual harassment — when Cuomo would sit in front of a PowerPoint and tell a nation made insane by quarantine what day of the week it used to be. “And I was like, ‘You can’t be serious.’ But you are!” Woodward Pusaid. “Obviously that’s not a physical interest. Or maybe it is. But Cuomo was seriously, hugely popular. I’d ask, “OK, why?” And they’d say, ‘He has such a commanding presence.’”

It’s not unusual for DC clients to mention specific names to their matchmakers like this. Typically, these asks aren’t literal so much as inspirational (or aspirational). “What women are ultimately looking for is the vibe,” said Woodward Pu.

Some clients, though, do come to matchmakers with very, very specific asks. One VIP TDR client requested his matchmaker set him up with Rep. Alexandria Ocasio-Cortez — a move that perfectly illustrates the hilarious and infuriating paradox of the straight male dater: devoted enough to his would-be girlfriend to drop thousands of dollars on a matchmaking service, but apparently incapable of Googling “AOC + boyfriend?” to find out that she’s been in a serious, long-term relationship since well before she ran for office.

“Oftentimes in DC guys will say, ‘this reporter, this news anchor, this woman is my dream woman,’ and we can go track her down to find her,” said Kat Markiewicz, a DC matchmaker who grew up in the District. TDR matchmakers will do “the dirty detective work,” as Markiewicz puts it, of sliding into a star’s DMs on their client’s behalf; TDR policy is to “always reach out to anyone [a client] is interested in,” said Talia Goldstein, founder of TDR.

Some DC men ask after celebrities who don’t live here (Chelsea Handler) or who not only don’t live here but are also married and definitely out of their league (Margot Robbie). Laricks says her gay clients seeking men bring up actor Matt Bomer a lot — not literally Matt Bomer, though, just someone who looks like him.

Straight Washington women, said the matchmakers, are crushing on their newscasters: CNN’s Jim Acosta, Fox’s Bill Hemmer, NBC’s Steve Kornacki during the height of khaki-mania. TDR has fielded several requests for Senator Cory Booker. (“I wouldn’t disclose it,” said Bernstein. “But I haven’t had contact with him.”)

Celebrity crushes often serve as a jumping-off point, as in the case of Markiewicz’s client who said his type was Modern Family’s Sarah Hyland. Markiewicz went out looking for “big-eyed, Disney princess-types” for him. “It’s not just about looks,” she clarified. “I’m going to probably talk to 50 Disney princess girls over the next six months, and I’ll pick out the three to six that end up being the best fit for him in other ways.”

The Requirements

“I need a guy who makes $500,000 a year or more”

Not everyone in Washington is hoping to be matchmade with someone they’ve spotted on TV. But more so than daters in other cities, the matchmakers say, DC daters know what they want — or, at least, they think they know what they want: an impressive educational pedigree (Ivy League or Stanford undergrad, plus a master’s); a formidable income (“Women say, ‘I need a guy who makes $500,000 a year or more,’” said Markiewicz); the social graces to thrive on the gala circuit; a well-stamped passport; and an ambitious and hard-working sensibility (“There is a total disdain for complacency in the average Washingtonian,” said Woodward Pu). (“We do match based on lifestyle,” added Callie Harris, who co-launched the DC Branch of TDR. Barring some exceptions, “We don’t match someone who flies first class everywhere with someone who makes $60,000 a year.”)

Within this platonic ideal of the DC partner, there are obviously some variations. Woodward Pu’s female high-rollers don’t care about money (“they have basically unlimited funds”) and instead prioritize civic-mindedness and passion. “Social justice is a huge piece for people in their later phases,” she said. “They’ve moved on from the focus on their own family. They’re becoming aware of their own mortality and thinking about what their legacy will be.”

Unsurprisingly, the matchmakers said that the number one deal-breaker for daters in this town is “Donald Trump supporter.” But while liberals aren’t into dating conservatives, conservatives can be open to dating people who are more progressive. And centrists are down to grab a drink with a Romney Republican, provided they agree on the basics (eg the election wasn’t “stolen”). TDR has 11 branches across America, and they don’t hear much about voting habits elsewhere. “I hate to call out LA specifically,” said Harris. “But I’ll talk to people out there, and they don’t care about politics at all.”

While some of these clients don’t live in DC — lots of Woodward Pu’s one-percenter women live in the middle of the country — many of them hope to be paired up with someone who does. Goldstein has one VIP client out in Los Angeles, a political fundraiser, who only wants to be matched with a Washingtonian. “He would move for the right person,” she said. “And he’s convinced she’s in DC.” TDR matchmakers say that, especially since Covid, geography is less of a barrier for singles than ever — with one notable, local exception. “It’s long distance to date someone in Arlington,” said Markiewicz. “There’s something about the Potomac,” she added. “It’s a weirdly big obstacle.”

What’s funny to the matchmakers is how often these wish lists fail to produce the match their clients desire. “It’s through a lot of conversations and setting them up on dates with people who went to Harvard and are six feet tall — and then they go out, and it’s an OK date, but it doesn’t work out,” said Bernstein, that clients learn to keep a more open mind. “People get so focused on what they think they need, or what society tells them they need for a ‘successful’ relationship, they lose a bit of their own identity.”

The Stakeout

“Not to catch you off guard, but are you single?”

four years ago, Bernstein was staking out one of her go-to spots for finding eligible, gainfully-employed bachelors — the Starbucks at L’Enfant Plaza — when someone caught her eye. He was a “very put-together gentleman,” she remembered. “I liked the way he carried himself.” She walked up to him and introduced herself: Hi, I’m a professional matchmaker. Not to catch you off guard, but are you single? He was intrigued enough to have his coffee with Bernstein, who learned that he was in his late thirties and a museum curator. She set him up with one of her clients, a woman around his age, and they’re still together today — more than six years later.

Where else are these matchmakers scouting for potential paramours? Along with that Starbucks, you might stumble across them if you swing by the Firehook Bakery on Capitol Hill during weekday lunch hours. They’ll also hit up the Doyle bar in Dupont during happy hour, handing out business cards to anyone who fits their clients’ ideal profiles (and has a bare ring finger).

For the one-percenters, much of the recruiting happens at galas and fundraisers. “You meet people who are single [and] affluent, because a ticket is $350,” said Woodward Pu. “The average person doesn’t have that on a Thursday evening.” The White House Correspondents Dinner and its surrounding social sprawl are a DC matchmaker’s Super Bowl. According to Woodward Pu, the socialite circuit is another popular track: the Butterfly Bash for “trendy” and “philanthropic” singles; Taste of the South “for a younger, preppy crowd.” She also likes the Young Members Happy Hours at the National Press Club for civic-minded singles.

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