How To End A Conversation

by Joe Berkowitz

We live in a social hellscape littered with talking heads, salesmen at the quota crisis point and acquaintances whose names we can’t remember. We recognize that the exchange of pleasantries must be endured for the world to work, and most of these conversations are well-rehearsed dances — routines that get the job done. But all too many others play out like cringe-inducing conga lines. Oh, the awkwardness! And then the ennui! Dealing with other people can make each day feel like a Double Dare-style obstacle course (look it up, youngs!), with a grand prize of merely not going to jail for assault at the end of it.

Which brings us to an important question: Why is everybody always the worst all the time? Not just strangers and acquaintances, but even friends and family!¹ Perhaps it’s because we’ve all gotten used to the idea of having so many lines of communication available, on our own timetables, all the time. Human conversation can feel so… obsolete these days. Conceivably, you could wear headphones and communicate in pantomime, waving off anyone interrupting each precious “doing” of “something,” the better to be left alone. If you wanted to be a dick about it, you could never have another boring conversation again.

But participation in the social condition isn’t optional, even if it is inconvenient. So what’s the best way to exit stage right when the conversation’s work is done? Most people can sense when another person’s mind has drifted elsewhere, and the nice ones will then do the heavy lifting of wrapping things up for you. Sometimes both participants will simultaneously recognize that a conversation has nowhere left to go and the situation then resolves itself naturally. But sometimes it’s going to be up to you to take action. Forcing a conversation into a half-nelson is a life skill that nobody should be without, like changing a tire or making a grilled cheese sandwich.

The situation: It’s a call you either wanted to take or had to take, but it’s now gone on too long.
Level of awkwardness: Low. The worst-case scenario is that the other person hears what you’re doing to keep from pulling the hair out of your own skull while the conversation drones on and calls you out on it. In which case you are about to either be hung up on or have an argument, which is at least sort of interesting.
How to handle: Phone calls are easy to disengage from thanks to lying! Anything in the world could require your attention as far as the other person knows. You don’t need a sound effect. You don’t need a third party to bail you out with a loud request for assistance. You are bound only by imagination. “Mandy Patinkin is about to serenade me” is completely acceptable.

The situation: That person you bought furniture from on Craigslist that one time? They are now a constellation in your Gchat-universe, and they’d like a word.
Level of awkwardness: Medium. The goal here is to extricate yourself from the person chatting you up without having to exit the application altogether. Is it okay to just leave that one chat-box down at the bottom of the screen open without a response? Will it be okay down there, or will it become sentient and angry?
How to handle: Take increasingly long pauses between responses. Apologize profusely and explain that you’re “putting out fires” or some such excuse, but then continue dragging out each response. Nobody can stand to be on the receiving end of that for long, and they’ll soon move on.

The situation: The moment that occurs immediately after you’ve run out of things to say while Skyping lasts an eternity. If you haven’t mutually agreed on an ironclad bailout-time, and the conversation falters, you’re completely at the mercy of the other person (whom you probably love, but still.)
Level of awkwardness: High. You can see each other. You can see each other think.
How to handle: Few things are more depressing than looking someone dead in the eye and lying about being superbusy, only to turn around and have to stare down the gaping maw of an empty room. ² Better in this case to let the conversation decompose organically. But if you’d like to avoid that, you should be able to wind things down after a long pause by looking around and saying “Okay, I guess I’ll let you get back to [whatever the person normally does with their time].”

The situation: Where to even begin? The smallest small talk in the world always emanates from the largest offices. It comes in many varietals: the shared elevator ride, the cubicle pop-in, the hallway haranguing, and on and on. Since so many people spend the majority of their time at their places of employment, they get to sample every flavor of this rainbow at some point or another.
Level of awkwardness: High. Your colleagues are like a second family that it’s okay not to love. Some of them are interchangeable and others are irreplaceable, but they all have one thing in common: You cannot afford their hatred. The people you see every day need to be handled with care, lest they mess with your reputation and career. This means you have to endure whatever perversely mundane thing they might choose to discuss during the longest coffee brew ever, while not seeming for one second as though you’re enduring it rather than enjoying it.
How to handle: At least 90% of all office conversations will end sufficiently well when you respond to a statement that carries even the faintest whiff of closure with a “Yes indeed” and a sage nod. Then get the hell out of there. Listen closely and you can turn anyone’s declarative statement into your exit line. Whatever happens, try to avoid emphasizing how busy you are. This salvo will be interpreted by the person you’re talking with as a passive-aggressive snipe suggesting that he or she is not busy, has never been busy, and couldn’t identify “busy” in a police lineup. Instead of vocalizing how busy you are, use body language. Angling your torso toward the nearest exit and twitching slightly is a useful signal that you’re late for something.

If the conversation is taking place in your office instead of theirs, just exaggerate the importance of every single distraction. Keep craning your neck toward your computer at every email ping, either real or imaginary. Nobody will refuse to pick up what you’re throwing down and keep you away from the results of the quarterly report or whatever. The only exception to this rule is if the person sitting across from you is either a boss or a client, in which case you maintain generous eye contact until your boss departs and/or the office lights are turned off for the day.

The situation: Basically, there are two opportunities for prolonged awkward conversation when shopping: a salesperson getting chummy because he just watched Glengarry Glen Ross and is determined to close your brains out, or someone who mistakes the casual friendly comment you threw out (because you’re a terrific person) as an invitation to a box social.
Level of awkwardness: Low. However bad it gets, you can literally run away in mid-sentence and it won’t go on your permanent record.
How to handle: Any way you want. You will probably never see these people again and no matter what you say, they’ve heard ruder. The most polite way to dispatch a chatty clerk is to leave him or her laughing. Whatever garbage comes out of your mouth doesn’t have to be funny; as long as it sounds remotely like a joke, any salesperson will know it’s time to bark out a laugh like a trained seal near a barrelful of mackerel. Then you can bid farewell and keep it moving. (Actually, this method works for any scenario. You can stop reading now.)

The situation: You see someone familiar on the platform. Your eyes lock. It’s that dude, Dennis, from that party that time. Unless a Michael Bay movie breaks out in the terminal in the next few seconds, the two of you are about to interface.
Level of awkwardness: Medium. Whatever you possibly have to say to each other will be entirely exhausted by the time the train arrives, but it would be rude not to ride together. Now you’re stuck talking to each other until one of you gets off. That, or you can pretend the next stop is your stop, get out there, and build a new life on Lorimer Street because it’s easier that way.
How to handle: On the bright side, Dennis could become your new best bud. This is how friendships flourish sometimes. However, if the payoff doesn’t seem worth the risk, there’s an opportunity to ditch him right when the train is approaching. You can beg off by informing him that your exit is near the opposite end of the subway. Nobody will ever challenge this claim. But if you do end up riding together and it is terrible, the silence between you must go on for at least one full minute before you can legally pull out headphones. At that point, you are only required to wave or nod when Dennis leaves.

The situation: The pain of being stuck in an unwanted transit conversation sinks to its nadir on a flight.
Level of awkwardness: High. Airplane conversationalists are often oblivious bores who pretend not to notice the hardcover book jacket you’re fingering so longingly. Or they’re terrified of flying and convinced that closing their mouth for too long will result in immediate fiery wreckage.
How to handle: Scraping this barnacle off your hull is going to be difficult. If you just whip out the usual sentences that begin with “Alright, well…” which you might use on a phone, you are still practically spooning each other for any number of uncomfortable hours. This proximity also makes an outright declaration of your intent to disengage impossible. Luckily, there is something about an airplane that naturally inspires drowsiness, making this the one social situation where it is 100% acceptable to fall asleep during. Fake-sleeping for a minimum of 20 minutes or so should sufficiently chasten your chatterbox — but not in a hostile way — allowing you to start watching Netflix without incident when you “wake up.” Worst-case scenario: You actually fall asleep.

The situation: When going out at night, there’s a fair chance of bumping into Dennis or his legion of brothers among the members of your extended group. If you’re a woman, you might also get hit on. Badly.
Level of awkwardness: Medium. Each of these scenarios is its own separate nightmare. Either way, it’s excruciating when you have nothing to say to the person standing two feet from you in a place with loud, booming music. The two extremes will weirdly bounce off and amplify each other until the words to whatever song is playing become like cartoon talk bubbles for an alternate version of what’s going unsaid. ³ This is assuming you’re not talking to the kind of person who would mark an awkward silence by pointing out that it is, in fact, an awkward silence (as though that ever helped out anything in the world).
How to handle: All you need to do is introduce a third party into the mix, and the first time the other ends of this triangle complete an official back and forth, you’re officially allowed to leave. As with the shopping situation, you only really have to endure this moment for as long as you feel the need to be polite. At any time really, you can start looking around as though you might have just spotted Judah Friedlander in the perimeter, and abruptly excuse yourself. Go to the bathroom for a while. Get a drink. Dance. You’re free.

¹ I’m not exempting myself here. If anything, I’m the worst of all.
² This is why I don’t Skype. I can’t even.
³ Something about “grinding.”

Joe Berkowitz edits books and writes stuff. He also has a tumblr.

Photo credit: NBC Photo/Mitchell Haaseth