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What It Really Takes to Work as a Matchmaker

Career

When I first got hired to work as a matchmaker for an elite dating service in New York, I assumed I'd have to transform myself into a version of Patti Stanger. Thinking about her blunt confidence, decisive nature, and occasionally brash tone made me nervous. After a year of dabbling in matchmaking as a hobby — I set up my college classmates and wrote about their blind dates for a column on my school's student-run blog — I was about to put my skills as a matchmaker to the test in a professional setting. I was terrified. On my first day of training, I was just 21 years old; my most formative romantic experience to date was getting dumped at a grocery store. Did I really have what it took to make it as a matchmaker?


During a series of training sessions, my fears were mostly put to rest. I learned that matchmaking is more of an art than a science, and that every matchmaker approaches it differently. I learned that my boss's academic background was in communications and her professional background was in the hospitality industry; she was intuitive, excellent at reading people, and had an ultra-soothing presence. Her style of matchmaking was based on understanding people's energy. Another matchmaker focused on offering coaching services to his clients, to make them feel as confident as possible on their dates. Another was naturally very social and liked to find fascinating matches for her clients while out with friends. The message was clear: as long as I followed a few basic principles of what makes a strong match, I could put my own spin on the job. I just had to figure out what worked for me.

I began the job with a small handful of clients, with the goal of taking on more as my skills progressed. Here's how it worked at my company: Clients paid $600 a month for two first dates with different matches. Matchmakers were always on-call to offer pre-date pep talks, outfit advice, and post-date analysis. Every time I was assigned a new client, I'd meet with them one-on-one to learn about their relationship history, what kind of relationship they're looking for now, what their lifestyle looks like, who they're attracted to, and so on. From there, it was up to me to find potential matches, screen them all to determine which one are a good fit, choose the winners, and arrange the dates. I found matches in our company's massive database of eligible singles, plus I used up to eight different dating apps and sites at a time, scoured my personal network, attended singles events, chatted up attractive people on the subway, and more.

I won't lie, matchmaking intimidated me. I'm an introvert, not a people person. I had zero experience tracking down the kind of successful, sophisticated, attractive, and charming people my clients expected me to deliver. I was afraid people would lose faith in my abilities once they realized how young I was.

But I had one asset on my side. Prior to matchmaking, I had studied journalism, worked as a reporter for my school's blog, and interned at a variety of magazines. I was a solid interviewer. And really, isn't the process of getting to know my clients and their potential matches deeply just a series of interviews? The skills I used as a reporter — researching my subject, acting approachable, asking smart questions, and listening well — translated directly into my work as a matchmaker. It's like what I learned in journalism school: You might not know everything there is to know about a topic when you begin reporting a story, but if you ask the right people the right questions, you'll get there.

It was exhilarating to feel myself learning new things every day, whether that was a list of which hotel bars in Manhattan took reservations and which didn't, or a profound lesson on love.

I loved matchmaking. It was my window into a new world. Sure, I might have been a 21-year-old who considered an eight-dollar bottle of wine to be a splurge, but my clients were glamorous, well-traveled 30- and 40-somethings with enviable careers. And I loved the adrenaline rush that came from toggling between dating apps, sprinting across the city to interview a match, and the sweet satisfaction of setting up a perfect first date. It was exhilarating to feel myself learning new things every day, whether that was a list of which hotel bars in Manhattan took reservations and which didn't, or a profound lesson on love.

I also learned the importance of finding a career that suits your personality. As much as I adored my job, I crawled into bed every night feeling drained. Keeping up an aggressive social façade while carrying on dozens of intimate, deeply difficult conversations a day was not my cup of tea. I found myself missing the relative calm of my old life, typing alone behind a computer. Even when I wasn't working, I didn't feel like myself. I didn't have the emotional energy to get through a date (for myself) after spending all day arranging dates for my clients.

Playing With Matches, By Hannah Orenstein

Ultimately, I scaled down my role at the company so I could return to college in the fall, and I left the position that winter so I could intern at a digital publication during my last semester of school. Once I graduated, I pursued work in media, as I had always planned — first, as a writer at Seventeen.com, next (drawing on my matchmaking experience), as the dating editor at Elite Daily. My first novel, Playing with Matches, came out earlier this year. It's about a young matchmaker who's in way over her head, drawing from my real-life experiences as exactly that. In the years since- I've set up a few couples on a purely recreational basis, but I have no interest in returning to my former career full-time.

I'm glad that I gave matchmaking a chance. It was a once-in-a-lifetime career opportunity and I'm so grateful that I tried something new. The experience truly changed my life. Even if I didn't stay in matchmaking for long, it taught me a valuable lesson: an amazing job isn't so amazing if it's not suited to your personality.

My best match yet? Picking a career — writing and editing — that makes me feel like the best version of myself.

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Politics

Do 2020 Presidential Candidates Still Have Rules to Play By?

Not too many years ago, my advice to political candidates would have been pretty simple: "Don't do or say anything stupid." But the last few elections have rendered that advice outdated.


When Barack Obama referred to his grandmother as a "typical white woman" during the 2008 campaign, for example, many people thought it would cost him the election -- and once upon a time, it probably would have. But his supporters were focused on the values and positions he professed, and they weren't going to let one unwise comment distract them. Candidate Obama didn't even get much pushback for saying, "We're five days away from fundamentally transforming the United States of America." That statement should have given even his most ardent supporters pause, but it didn't. It was in line with everything Obama had previously said, and it was what his supporters wanted to hear.

2016: What rules?

Fast forward to 2016, and Donald Trump didn't just ignore traditional norms, he almost seemed to relish violating them. Who would have ever dreamed we'd elect a man who talked openly about grabbing women by the **** and who was constantly blasting out crazy-sounding Tweets? But Trump did get elected. Why? Some people believe it was because Americans finally felt like they had permission to show their bigotry. Others think Obama had pushed things so far to the left that right-wing voters were more interested in dragging public policy back toward the middle than in what Trump was Tweeting.

Another theory is that Trump's lewd, crude, and socially unacceptable behavior was deliberately designed to make Democrats feel comfortable campaigning on policies that were far further to the left than they ever would have attempted before. Why? Because they were sure America would never elect someone who acted like Trump. If that theory is right, and Democrats took the bait, Trump's "digital policies" served him well.

And although Trump's brash style drew the most handlines, he wasn't the only one who seemed to have forgotten the, "Don't do or say anything stupid," rule. Hillary Clinton also made news when she made a "basket of deplorables" comment at a private fundraiser, but it leaked out, and it dogged her for the rest of the election cycle.

And that's where we need to start our discussion. Now that all the old rules about candidate behavior have been blown away, do presidential candidates even need digital policies?

Yes, they do. More than ever, in my opinion. Let me tell you why.

Digital policies for 2020 and beyond

While the 2016 election tossed traditional rules about political campaigns to the trash heap, that doesn't mean you can do anything you want. Even if it's just for the sake of consistency, candidates need digital policies for their own campaigns, regardless of what anybody else is doing. Here are some important things to consider.

Align your digital policies with your campaign strategy

Aside from all the accompanying bells and whistles, why do you want to be president? What ideological beliefs are driving you? If you were to become president, what would you want your legacy to be? Once you've answered those questions honestly, you can develop your campaign strategy. Only then can you develop digital policies that are in alignment with the overall purpose -- the "Why?" -- of your campaign:

  • If part of your campaign strategy, for example, is to position yourself as someone who's above the fray of the nastiness of modern politics, then one of your digital policies should be that your campaign will never post or share anything that attacks another candidate on a personal level. Attacks will be targeted only at the policy level.
  • While it's not something I would recommend, if your campaign strategy is to depict the other side as "deplorables," then one of your digital policies should be to post and share every post, meme, image, etc. that supports your claim.
  • If a central piece of your platform is that detaining would-be refugees at the border is inhumane, then your digital policies should state that you will never say, post, or share anything that contradicts that belief, even if Trump plans to relocate some of them to your own city. Complaining that such a move would put too big a strain on local resources -- even if true -- would be making an argument for the other side. Don't do it.
  • Don't be too quick to share posts or Tweets from supporters. If it's a text post, read all of it to make sure there's not something in there that would reflect negatively on you. And examine images closely to make sure there's not a small detail that someone may notice.
  • Decide what your campaign's voice and tone will be. When you send out emails asking for donations, will you address the recipient as "friend" and stress the urgency of donating so you can continue to fight for them? Or will you personalize each email and use a more low-key, collaborative approach?

Those are just a few examples. The takeaway is that your online behavior should always support your campaign strategy. While you could probably get away with posting or sharing something that seems mean or "unpresidential," posting something that contradicts who you say you are could be deadly to your campaign. Trust me on this -- if there are inconsistencies, Twitter will find them and broadcast them to the world. And you'll have to waste valuable time, resources, and public trust to explain those inconsistencies away.

Remember that the most common-sense digital policies still apply

The 2016 election didn't abolish all of the rules. Some still apply and should definitely be included in your digital policies:

  1. Claim every domain you can think of that a supporter might type into a search engine. Jeb Bush not claiming www.jebbush.com (the official campaign domain was www.jeb2016.com) was a rookie mistake, and he deserved to have his supporters redirected to Trump's site.
  2. Choose your campaign's Twitter handle wisely. It should be obvious, not clever or cutesy. In addition, consider creating accounts with possible variations of the Twitter handle you chose so that no one else can use them.
  3. Give the same care to selecting hashtags. When considering a hashtag, conduct a search to understand its current use -- it might not be what you think! When making up new hashtags, try to avoid anything that could be hijacked for a different purpose -- one that might end up embarrassing you.
  4. Make sure that anyone authorized to Tweet, post, etc., on your behalf has a copy of your digital policies and understands the reasons behind them. (People are more likely to follow a rule if they understand why it's important.)
  5. Decide what you'll do if you make an online faux pas that starts a firestorm. What's your emergency plan?
  6. Consider sending an email to supporters who sign up on your website, thanking them for their support and suggesting ways (based on digital policies) they can help your messaging efforts. If you let them know how they can best help you, most should be happy to comply. It's a small ask that could prevent you from having to publicly disavow an ardent supporter.
  7. Make sure you're compliant with all applicable regulations: campaign finance, accessibility, privacy, etc. Adopt a double opt-in policy, so that users who sign up for your newsletter or email list through your website have to confirm by clicking on a link in an email. (And make sure your email template provides an easy way for people to unsubscribe.)
  8. Few people thought 2016 would end the way it did. And there's no way to predict quite yet what forces will shape the 2020 election. Careful tracking of your messaging (likes, shares, comments, etc.) will tell you if you're on track or if public opinion has shifted yet again. If so, your messaging needs to shift with it. Ideally, one person should be responsible for monitoring reaction to the campaign's messaging and for raising a red flag if reactions aren't what was expected.

Thankfully, the world hasn't completely lost its marbles

Whatever the outcome of the election may be, candidates now face a situation where long-standing rules of behavior no longer apply. You now have to make your own rules -- your own digital policies. You can't make assumptions about what the voting public will or won't accept. You can't assume that "They'll never vote for someone who acts like that"; neither can you assume, "Oh, I can get away with that, too." So do it right from the beginning. Because in this election, I predict that sound digital policies combined with authenticity will be your best friend.