Illustrations by John Broadley
Jessica M. Goldstein is a freelance writer based in Washington, D.C. She is a contributing editor to Washingtonian and a contributing writer to the Washington Post’s Arts & Style section and Magazine.
In D.C. dating, obstacles abound. Everybody is busy and nobody texts back, or they text and text but never plan a date, or they date once only to ghost. All the “moderates” are secretly conservative; a lot of the liberals are not-so-secretly annoying. The pandemic shut down the party scene, but swiping on the apps is such a drag — and isn’t really an option for D.C.’s more high-profile singles. So perhaps it’s not surprising that an old-timey way of finding love has made something of a comeback: D.C.’s single power players are enlisting matchmakers in their dating searches.
You could do it, too. For several thousands of dollars a month — double what the average person spends on rent for a one-bedroom in D.C. — this matchmaker will not only seek out potential soulmates with your exact criteria in mind but will do the sort of investigative work that, coming from you, would seem invasive and creepy — trawling LinkedIn for singles with degrees from prestigious universities, or NextDoor for homeowners in affluent zip codes, or LegiStorm for Congressional staffers’ bios, salaries and contact information. They can also help you navigate the obstacles very particular to dating in D.C., like how to keep your dating life off Twitter and out of the pages of this magazine, or how to make it clear that you don’t share all of your boss’ political views.
For the inside intel on how these services work and who uses them, I spent the spring calling up a murderers’ row of D.C. matchmakers. The biggest brand in town is Three Day Rule (named ironically, for the Swingers-era counsel to wait three days before calling a woman you want to see again), a national outfit that launched its D.C. branch in 2015. To be a client and all that entails — a guaranteed minimum of one match per month, plus coaching, a photoshoot and post-date debriefs — costs $5,900 for three months and $9,500 for six. (TDR also offers VIP packages, which start at $18,500 and let daters get more involved in the search and selection process.)
Who in the capital is signing up? When it launched in the city, TDR’s clientele was mostly 35 and up. But the demographic gets younger by the year, with many twenty-somethings now exploring what their services have to offer. Some clients are low-paid Capitol Hill staffers whose parents, the matchmakers theorize, likely spring for the service. Plenty are upper-middle-class types — lawyers, consultants, more lawyers. And about a quarter of TDR’s clientele are what Jaime Bernstein, a senior matchmaker in D.C., describes as the “very elite, high-profile power players in the D.C. scene.”
These matchmakers wouldn’t be in business if they couldn’t be discreet, but they could still share a pretty detailed description of the “elite” daters on their roster. Such clients include: TV hosts; ambassadors; political fundraisers; children of senators; attorneys at the Department of Justice; high-up folks at Treasury, IMF and the SEC; owners of political consulting firms. TDR has been hired by the owner of a D.C. sports team, a speechwriter for Michelle Obama, and politicians in various stages of running for office looking for their campaign trail plus-one.
Different matchmakers specialize in different demographics: Kara Laricks is an LGBTQ+ matchmaker, who has some D.C. clients dreaming of being, she told me, “half of a power couple that will be seen on the red carpet, at the Correspondents Dinner,” while Quin Woodward Pu clicks with the uber-rich, AARP-card-carrying female set: heads of foundations, heiresses. “She’s the super wealthy woman that has multiple philanthropies at one time, even if she doesn’t have a job,” Woodward Pu said. “She leads a multi-million or multi-billion-dollar organization.”
These power players might be able to mint money and impeach presidents, but D.C.’s matchmakers report that, in love, the elite are as hapless as the masses, and in some ways even more so: Necessarily concerned with privacy and discretion, many won’t risk exposure by setting up profiles on Bumble or Hinge; traveling constantly for work or employed in high-security-clearance jobs (e.g. CIA, Pentagon) where they are separated all day from their personal devices, they’re hardly available for the swiping and text-flirting required to stay in the game; judged prematurely by paramours they meet in the wild who recognize them from TV, they rarely get an honest chance to make a first impression.
And: At ease in positions of authority and practiced in the art of the no-comment comment, these Washingtonians aren’t exactly comfortable being vulnerable and open — which is to say, their dating acumen can trail way behind their professional prowess.
“People like this, especially in D.C., they’re used to getting what they want,” said Woodward Pu. “They can work harder or smarter or get a connection for it. And this is the one place they have not been able to figure out. It’s very vexing for them, and it’s very vulnerable. People are coming to us with a level of vulnerability that they’ve probably never experienced or shown ever.”
“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 was. “And I was like, ‘You can’t be serious.’ But you are!” Woodward Pu said. “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 D.C. 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 D.C. 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 D.C. 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 D.C. 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.”
“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, D.C. 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 D.C. 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 D.C. 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 (e.g. 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 L.A. specifically,” said Harris. “But I’ll talk to people out there, and they do not care about politics at all.”
While some of these clients don’t live in D.C. — 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.”
“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? Before the pandemic you might have stumbled across them at the Firehook Bakery on Capitol Hill during weekday lunch hours. (It’s closed now.) 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 D.C. 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, preppier crowd.” She also likes the Young Members Happy Hours at the National Press Club for civic-minded singles.
The Set Up
“They don’t want someone that’s going to fanboy”
Once the match is made and both parties have agreed to a date (after seeing each other’s photos and bio), TDR’s policy for straight dates is to give the man the woman’s phone number and tell him to call her, even if the woman is the client, unless someone specifically requests otherwise — which, reportedly, they rarely do. “These women [are] incredibly accomplished. They could certainly go after a man, but they feel like a guy might judge them for that a little bit, or they just don’t want to,” said Markiewicz. “They go after everything else in their life, and this time they want to sit back and have someone come to it.” (In her LGBTQ+ matches, Laricks always gives both daters each other’s numbers and jokes that whoever texts first wins. “I put everybody on even footing from the get-go,” she said. “Because that’s what it should be.”)
What about single people with security details? Can they just give out their phone number to strangers? Not quite. Markiewicz tells all her powerful clients to get a Google Voice number they can use exclusively for dating. “If something were to go awry … just scrap that number, you don’t have to have it connected to your phone anymore.” And though TDR matchmakers don’t plan the dates, Markiewicz says she’ll advise her more public-facing clients to avoid the usual haunts — no Cafe Milano, nowhere on the Hill. Better to find “a dark corner in Old Town,” she suggests, where you’re less likely to be seen.
TDR protects the identities of their most famous clients during the matchmaking process, but only to a point: Names are anonymized until the match is made, at which point both daters get to see each other’s photos and first names (but not last names or places of business). Celebrity clients “are aware that people have heard of them,” Woodward Pu said. “But they don’t want someone that’s going to fanboy. They don’t want someone that’s going to be uncomfortable with their wealth and is totally out of their element talking to a billionaire — which, to be fair, most people are! So when you mention, ‘This person comes from billions of dollars,’ [you’re looking to find out], how do they respond?”
Contrary to the fantasy many civilians harbor, fame can be more of an obstacle than an accelerant when it comes to finding someone to date. Michelle Jacoby, founder and CEO of D.C. Matchmaking, another matchmaking service in the capital, recalled trying to match a client with “an internationally well-known person in the D.C. area who didn’t want people to know who she was.” It proved impossible. “There was no way to dance around her fame. … You don’t really want to go on a date with a famous person without knowing it’s about to happen.”
Markiewicz understands why those famous clients are apprehensive about dating people who would recognize them on sight. “[Clients] might be people that are on TV frequently and they don’t want people going after them for the wrong reasons and thinking, oh, I can have influence and power by getting close to this man [or woman] who has influence in power,” she said. “Some of it is a very Washington problem because if you’re up on Capitol Hill and you’re on C-SPAN, you don’t want someone to know you’re available and out there.”
One of Woodward Pu’s clients “was a public-facing communications professional for an administration.” (Woodward Pu lived in D.C. through Obama and Trump). According to Woodward Pu, “she was struggling because… everyone knew who she was” and though she was “actually more moderate than the president,” his reputation turned off potential matches. Woodward Pu told eligible men all about this person’s off-the-clock life and the parts of her job that didn’t make the evening news, trying to “humanize someone that can look like a pit bull,” she told me. “If you can make people realize they have a soft side — then you realize that actually this is just a person capable of giving and receiving love.”
“The truth is, you can’t put Pandora back in the box,” Woodward Pu said. “It is what it is. If they’re out there, and they’re a celebrity of some degree, that just is what it is and we can’t pretend they’re not.”
The Post-Date Breakdown
“The two-phone thing is extremely D.C.”
Once the date is over, clients and their matches are interviewed by the matchmaker, who in turn provides a review to the other party. Fair to say this is not the part of their process these powerful clients enjoy most. “That is very challenging for politicians and talking heads,” said Woodward Pu. “People who are used to speaking but not receiving feedback in real time.”
Their reactions to hard-to-hear reviews can range from “surprise” to “I don’t want to say denial, because that’s too strong,” Woodward Pu said. “But Washingtonians want more evidence.” Told that they have a certain annoying mannerism or behaved in an off-putting way, they’ll ask for data to back it up. That said, “Washingtonians really do actually want things to work,” said Woodward Pu, so while the initial response can be shock, ultimately clients come around.
What “feedback” do these daters require? Markiewicz confided, with a wry smile, that it is not rare for D.C. men to begin the night by placing not just one but two phones on the table — a personal phone and a work phone, a doubling-down on the silent statement that they are very important, practically too important to even be on this date. Laricks has just started “proactively” having the conversation with her clients in their 20s and 30s: “I know that you’re busy. I know you may need to respond to things. But if dating is a priority to you, trust me on this, you will stand out from the crowd if you just put your phone away for an hour.” (The phones-on-the-table thing is a phenomenon across genders and sexual orientations and geographic boundaries, but the two-phone thing is extremely D.C., and, said Markiewicz, “usually male.”)
As for women, a lot of the criticism they get from men (via the matchmakers) pertains to their body language. Some of the women sit with their arms pretzeled across their chests, signaling to their date that they are closed off and not particularly interested, when in fact they are just protecting their bare arms against the arctic assault of the air conditioner. Men also complain that D.C. women only talk about work — “It felt like an interview” comes the post-date feedback — while women complain that D.C. men only talk about themselves. In D.C., literally no one knows what to do when the check comes. (Though Woodward Pu, a Georgia native, thinks there is “confusion nationwide” on this subject.) Women typically offer to split the bill just to be polite, expecting the guy to insist on picking up the tab; meanwhile, men tend to see a woman’s offer to split as genuine and don’t want to undermine her autonomy. And some straight men get upset when women aren’t “grateful” enough that they’ve picked up the tab, the matchmakers say.
Miraculously, some daters overcome these barriers and make it way past date one, like the female partner at a lobbying firm whom Markiewicz matched with a campaign finance attorney back in early 2021. Since pandemic restrictions limited dining-out options, they spent their first date eating homemade pizza from the outdoor brick pizza oven he’d purchased as a Covid splurge for his kids. They’re still together. A foreign service officer found TDR because she struggled with dating while working in a job involving long stints overseas; Harris set her up with an adviser at the Treasury Department, and they’ve been together for more than five years now.
And for what it’s worth, every TDR matchmaker swore up and down that D.C. is a fantastic place to date — Bernstein went so far as to crown the District “one of the best cities for dating,” period. Allegedly a haven for those who prize substance over surface, our area is, according to these experts, an ideal place to find a serious match. Although you might have to suck it up and go to Virginia to find them. “I always tell women it’s worth crossing a bridge for a guy,” Markiewicz said. “Because you just never know.”