Is It Uncool to Flirt on LinkedIn?

If you think about it, it's not actually that weird.
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Christoph Niemann

Is flirting on LinkedIn less weird than on other social media? After all, it can vouch for you in a substantive way.

Whoa. Hang on. Let’s first poke at the premise of your question, because the implications here are huge. Notice how you casually presume your résumé offers a more substantive representation of your basic humanity than, say, all the tweets you’ve tweeted or all the digital artifacts amassed on your Facebook page. Think of the photos on Facebook alone: You in a rowboat with the gentle-looking man playing a banjo whom we understand to be your deceased (too young) father. You being silly—but not obnoxiously silly, just innocently, endearingly silly—in the Halloween aisle of a big-box store. You tagged in a photo of that kid you mentored that one summer, as he graduates from Berkeley. You climbing a goddamned mountain! Like, with pickaxes and stuff!

Do these not substantively communicate the substance of your life? Don’t they “vouch” for you to potential dates as a safe, noncreepy, sufficiently together human being, a sympathetic soul tumbling through the fundamental experience of being alive and looking for companionship? Or is that better captured with a line like this: “January 2013-November 2014, Senior Operations Associate, Mobitly Inc.”?

You seem to think it is. And I’ll admit—begrudgingly—that you may have a point. Because the lines have been blurred between our work lives and our emotional lives, our careers and our intrinsic selves. We subconsciously gauge a person’s character by their professional standing, and our experiences and attitude toward our work aren’t only sometimes relevant to our love lives. In fact, the two can feel crucially interwoven: The best startup founders are those who operate out of passion and devotion and with a kind of hyper-monogamous obsession. On the other hand, we all feel obligated to work on our relationships with the same myopic, idealistic intensity. And it can feel natural to apply the lessons we learn relating to people in one realm to our relationships in the other.

Take, for example, Jeff Weiner, LinkedIn’s CEO. I confess, I’m not a LinkedIn user, but I’ve been reading up on Weiner and, I have to say, he seems like a wonderful guy—a principled, thoughtful man who says very grounded, Jerry Maguire-type things like, “I’ve never been title-driven; for the most part, I’ve been purpose-driven.” He also reads books by the Dalai Lama, contemplates the difference between compassion and empathy, and practices mindfulness techniques like “being a spectator to my own thoughts,” which enhance his ability to relate to and motivate his employees. He calls his style “compassionate management.”

In an essay he wrote a few years ago, Weiner described leaving work one evening, feeling proud of the strides he’d made as a compassionate manager, only to be felled by the epiphany that he’d been very uncompassionately neglecting his wife. He was working so hard, he wrote, that at night, “when my wife would try to bring up her day, or talk about the things we need to get done, I would reflexively say something to the effect that it had been a long day, I was exhausted, and could we talk about it some other time?” In other words: “For as hard as I worked to manage compassionately at the office, I was not always actively applying the same approach with my family.” So Weiner applied the same compassionate management style to his marriage and made things right.

I worry that sounds off, like the emotionally tone-deaf insights of a stereotypical tech baron. But trust me, the way Weiner explained it, it sounded cool—real. (And know this too: Worried that I’d gush in this column about Weiner’s coolness and realness only to learn later that Weiner is actually not cool and not real and is, in truth, as imperious as Genghis Khan or a Grade A, misogynistic, steroidal jerk, I sat down and Googled “Jeff Weiner LinkedIn jerk” and was happy to find, as the first result, a post singling him out as a “counterweight” to the industry’s many other CEO-jerks. So that was reassuring—even if the post was published on LinkedIn. But even that can be interpreted as a testament to Weiner’s character, because it was Weiner, I learned, who had the vision to expand LinkedIn from a bland résumé farm into a successful publishing platform.)

I’ll go even further. I wouldn’t be surprised if a man as smart as Weiner already knows all this, knows that we live in an age where one of the prime, romantically reassuring things about another person—the thing that “vouches” for them best as a potential mate—is that they’re a trustworthy, hardworking, successful employee. And therefore, he also secretly knows that LinkedIn could be the ultimate dating site, though he wisely stops short of saying it. Instead, he just dog-whistles about that potential to attentive users and eagle-eyed investors, thus preserving the opportunity to pivot the company explicitly in that direction should the climate change and the need arise. Recently, for example, he told an interviewer, “Our core value proposition to members is to help them connect to opportunity,” and touted “the power of this as a platform to enable capital”—especially “human capital”—“to flow where it can best be leveraged.”

Isn’t he talking about dating, about setting people up? When Tevye and Golde’s daughters sang, “Matchmaker, matchmaker, make me a match,” weren’t they basically asking a kind of social networking platform to send their own human capital flowing toward whichever shtetl boy would give it the highest valuation and invest? Why shouldn’t you flirt on LinkedIn? Why shouldn’t love be one of the opportunities LinkedIn connects us with?

So, yes. You are right. And you’ve taught me a lot—you and Jeff Weiner both. I can see clearly now how we’ve all tied ourselves into a knot of careerism and affection and equity and sex, and maybe that’s just the way it has to be. I’m remembering now what happened when Jerry Maguire—the real Jerry Maguire—showed up in that living room, shivering, trying to win back his wife, who also happened to be his business partner at their new sports-agenting startup, how he told her, “You ... you complete me.” But, more important, there was the line he slipped her right before that famous line. Suddenly, in the middle of his monologue, he was compelled to say, like a man giving a keynote at a conference, “We live in a cynical world, a cynical world, and we work in a business of tough competitors.”

Why? Why include that? What could Jerry Maguire possibly have meant? I think he meant: The internet is full of sinister strangers. It’s a hostile place in which to offer up your soul. But here I am. Look at me. View my profile. I’d like to connect with you on LinkedIn.