How to manage office relationships—on Slack, on Tinder, and out of office

On navigating working relationships and friendships—or maybe more—with co-workers

As the space between work and not-work becomes ever more blurred, questions about how to do this thing we plug away at for 30 or 40 or 70 hours a week become all the more expansive. In this column, Work Flow, we’ll delve into the novel dilemmas created by the new ways we work, as well as timeless questions about ethics, gender assumptions, and toxic work situations (and how to escape them). How we work is an important component of how we live—and we’re here to help you do better at both.

Something messing with your flow? Unload your work problems here, and you’ll not only feel heard, but you’ll also get unbiased, real-world advice. (That’s something your work sibling/spouse just can’t offer.) Tell us everything:

I Tinder swiped right on someone I recognize from the office. They apparently did the same: We matched. What next? Can I mention it when we’re both in the kitchen at the same time, or do I have to wait to make the next move in-app?

These are the trials of our digital times! I will tell you, I once swiped right on my favorite SoulCycle instructor, and suddenly, there we were—a match. Which really meant nothing except that I stopped going to SoulCycle. Was I really going to go on a date with a guy who instructed us to shout “Love!” over and over as we peddled through the dark? What would we even talk about? It was all too awkward, the idea that I might have to do something about this match. So I did nothing.

I didn’t really want to go out with my SoulCycle instructor, but there’s that weird thing that happens on Tinder when you see someone you know or sort of recognize: You swipe right as a wink, Hey, I see you—and maybe you hope they’ll do it back, but does that mean you actually want to date them? Unclear. The truth is, sometimes the barriers by which we compartmentalize our various daily activities should not be crossed. So, ask yourself: Do you actually want to go out with your officemate? Presuming you both work for the same company, ask yourself, also, whether there are any workplace policies against it. If so, ask yourself if you prefer your job to this potential date. Ask yourself what would happen if things go awry… because you can’t just stop going to work the way you can stop going to SoulCycle.

If you’ve determined this is very well your best (or even just a decent) chance at love in these desperate times, I would make the next move in-app. Keeping the conversation where it began allows you to figure out a few things before you head into the open air together. Do you feel yourself connecting with this person? Are you having fun talking? Or is the bloom off the rose before the third message even arrives? This is important research that will inform your next move.

But! If you do find yourself running into your match at any point in time, I don’t suggest ignoring them completely as I did with my SoulCycle instructor. You might as well look them in the eye, give them a smile, and say hi. Maybe even ask a question: “You work in sales, right?” “Ooh, you love Lunchables, too?” Or something much smoother—it’s your flirtation! Put out into the world what you’d like to get in return… and then see what comes back. The wheels of a bike go ‘round and ‘round.

When you see a co-worker in a public place, are you obligated to talk to them? What if it’s during your commute? What if it’s in the waiting room of your therapist’s office?

You are never obligated to talk to anyone in any place, public or private. We are all busy adults going about our lives in the working and nonworking world, and it’s simply not reasonable to expect any person we recognize (not a good friend—the rules are different then) to drop everything and just communicate when we see them.

This is where it would be helpful to have signs on our foreheads that flash green for “open to conversation,” yellow for “maybe,” and red for “do not disturb.” But we do not, so read their body language instead. If the person you recognize is reading a book, or staring at their phone, or deep in meditation or thought or sleep, just let them be. If they’re hunched in a corner, trying not to engage with anyone, read that. You work with them, you can always talk to them later. If the person you recognize is looking around the train car, their eyes light upon you, and they smile, you should respond—but it’s totally OK to simply smile back, or give a wave and a nod, and then return to your book or phone or commute-nap. (If they’re weeping profusely, it never hurts to say, “Hey, are you OK?” and pass them a tissue.) The key here is, indeed, “recognize.” Be human, politely acknowledge the existence of someone else on this planet—of everyone else on this planet, really—and then go on with your day.

As for the waiting room of your therapist’s office, there’s nothing wrong with a polite nod if you happen to make eye contact—therapy should not be considered anything shameful; in fact, you should be commended for going—but let them be, just as you’d hope they’d let you be. (Bring all this up to your therapist, though—it will surely stimulate some interesting conversation about boundaries.)

In a time of Slack and omnipresent email and 24-7 expected responses, what is the most not-annoying way to remind someone that you’re still waiting for them to get back to you on something?

The expectation that everyone will respond to a digital request within five minutes is a kind of tyranny, but the plus is, if you have to wait for someone to respond to you, well then, maybe they have to wait for you, too. Truth be told, we could all slow it down a bit and be just fine, if not better, than we are.

This problem is exacerbated by the fact that you just can’t know what’s on the other side of the email—in this other person’s computer and their mind. You can only control what’s on your side. This person may be blowing you off; they may be legitimately busy; they may have forgotten;, they might not have gotten your request at all, or they may not know what to do with it. They might have gotten laid off—who knows?—or they’re simply in their own weird spiral.

It doesn’t matter, really: What you can and should do is politely follow up. Do it nicely, don’t be too demanding, don’t send too many emails, or write back too quickly. “Hi, just checking in on this! Let me know what I can do to help move things forward” is a fine message to send, but never more than once in the same 24-hour period.

There is research indicating that if you don’t get a response in 48 hours, you might never get a response at all. Live with that fact, but also: Follow up at least once or twice—more, depending on what’s at stake (make sure to vary your note upon repeat sendings). And you may want to move to a phone call if those stakes are high and you don’t get an answer digitally.

Sometimes, unfortunately, you just have to wait. In the interim, check the non-responder’s social-media accounts to make sure they’re alive. This may not make you feel better, but it’s something to do.

Interested in workspace? Get in touch.