Tinder too overwhelming? Well, there’s always a matchmaker

Today in crazy jobs that are real: tech-enabled matchmaker. Meet the D.C. outpost of Three Day Rule.

Matchmaking isn't a new concept, but, ironically, technology helps it continue to exist in the modern era. (Photo by Flickr user minm01, used under a Creative Commons license)
In the age of Tinder, real-life matchmakers are still very much in business.

Before we meet Callie Harris and Jaime Bernstein, consider this: According to research by Pew, online dating and the positive, accepting attitude toward it has only grown in the past few years. And of course the market has responded in kind — dating sites and apps are all over the place. You’ve got and eHarmony and Tinder and Bumble and Hinge and then a whole host of more specific options like JDate for Jewish singles and FarmersOnly for, yes, farmers and so many others.

Callie Harris. (Courtesy photo)

Callie Harris. (Courtesy photo)

In a way this is great — it has certainly expanded our ability to find a special someone to an unprecedented high. But on the other hand, as is the case with many aspects of life in the digital age, all the options out there can be overwhelming. Some find themselves immobilized by all the choices to be made — it’s the paradox of choice, really.
This is where a modern matchmaker comes in, if you can afford it.
Harris and Bernstein work for a company called the Three Day Rule. The company was founded in Los Angeles in 2010, and has since expanded to key metro areas around the country. The D.C. branch launched in January 2015.
Here’s how it works:
Anyone can sign up to be a part of the Three Day Rule free pool. According to Harris and Bernstein, there are over 10,000 D.C. area singles in this pool. Simply signing up gets you an in-person meeting with a matchmaker where you go over your background, lifestyle, interests, dating desires and more. That’s where, if you’re a free user, your agency in the interaction all but ends. Harris or Bernstein might reach out if they have a paying client they think you could match with, but beyond that your profile, along with the rest of the 10,000, is stored away in a backend only Harris and Bernstein can access.
Jaime Bernstein. (Courtesy photo)

Jaime Bernstein. (Courtesy photo)

If you’re a paying client, though, your matchmaker will come back from the initial meeting and search this database for matches.
This is where technology comes into play.
Individuals can be sorted through a variety of tags and also using facial recognition software. Apparently, people like to supply pictures of an ex, hoping to find someone with a similar face. ?
Once the matchmaker has a match, she’ll reach out to ensure that this potential match is actually interested in a date, saving the paying client the sting of off-the-bat rejection. If the potential match is indeed interested, the man (no matter whether he or the woman is the paying client in this equation) gets the woman’s number to set up a date. Apparently, “women still like to be pursued.” Ah, 2016. (Note: Three Day Rule does not yet do LGBT matchmaking.)
After the date, both parties are asked to review it, and the paying client gets to sit down with Harris or Bernstein again to hear, in a nutshell, how it all went. Three Day Rule offers “date coaching” if needed.
Rinse and repeat! Of course, this kind of curated experience comes with a price tag. Three months with Three Day Rule will run you $4,500, while six months in $7,000. For professionals tight on time but not disposable income, apparently, this is a deal worth making.
On the matchmakers side, both Harris and Bernstein clearly love their jobs. They work independently in D.C., both setting their own schedules and taking on their own clients. Bernstein says she initially started matchmaking back in middle school — she’s got a “natural passion” for it. Harris, on the other hand, puts it this way — her big strength lies in connecting people, romantically or otherwise. “I’ve been a connector for as long as I can remember,” she laughs.
Working in the dating realm is extra fulfilling, though. “It has made me so much more open,” Harris says, adding that she really believes that there is something wonderful about every person she meets. Bernstein says she appreciates how uniquely personal yet universal dating, and the search for love, is.
Asked what the most surprising thing that’s ever happened in their lives as matchmakers is, both Bernstein and Harris struggle to answer. They take pride in not being surprised by anything, in realizing that each person they meet has very individual interests and desires. “I probably have more conversations about sex in an average day than most…” Bernstein finally offers.
So there you have it, matchmaking in the 21st century: facial recognition technology and an above-average number of conversations about sex.

Before you go...

Please consider supporting to keep our independent journalism strong. Unlike most business-focused media outlets, we don’t have a paywall. Instead, we count on your personal and organizational support.

3 ways to support our work:
  • Contribute to the Journalism Fund. Charitable giving ensures our information remains free and accessible for residents to discover workforce programs and entrepreneurship pathways. This includes philanthropic grants and individual tax-deductible donations from readers like you.
  • Use our Preferred Partners. Our directory of vetted providers offers high-quality recommendations for services our readers need, and each referral supports our journalism.
  • Use our services. If you need entrepreneurs and tech leaders to buy your services, are seeking technologists to hire or want more professionals to know about your ecosystem, has the biggest and most engaged audience in the mid-Atlantic. We help companies tell their stories and answer big questions to meet and serve our community.
The journalism fund Preferred partners Our services

Join our growing Slack community

Join 5,000 tech professionals and entrepreneurs in our community Slack today!


Major state funding boost means more Maryland college students can get tech internships

Tech companies spent over $342M on lobbying while laying down stakes in DC

He started at Neya as an intern. 10 years later, he’s director of robotics — and loving life

Women still fight for a seat at the tech industry table, even if bias is 'more subtle' these days

Technically Media