Last Resort Ways To Keep A Conversation Going When You Must Talk To Someone

You're talking to someone. You're doing a reasonable job on your end of keeping the conversation going, but it still feels stilted. Maybe the other person is giving you a lot of one-word answers, or you don't seem to have a lot in common. Usually you can try a few more strategies to turn the interaction around, like asking more open-ended questions, or casting around for a topic you both want to talk about. However, if you make a handful of attempts and things still feel halting and awkward, you can conclude you gave it an honest shot, but the other person isn't pulling their weight, for one reason or another. You can politely excuse yourself, or let the chatter peter out and turn your attention to something else. Like you could casually pull out your phone to check your messages, to send a, "We don't need to keep talking" message.

On rare occasions you'll be stuck in a labored conversation with someone, and leaving or staying put but disengaging isn't an option. Even if speaking to them is like pulling teeth, you're expected to keep a dialogue going. For example, you may be visiting your boyfriend's parents' cottage, and get stuck alone with his quiet mother while he and his Dad run an errand in town. It's a chore to talk to her, but it would seem rude to stop trying.

If the usual tips to jumpstart a flagging conversation don't work, and escape isn't an option, here are some last resort things you can try. Some of them are a bit insincere or manipulative, and won't lead to an exchange that's fun or fulfilling on your end. At this point it's not about being principled or having a blast. You just need to fill the air time.

Here are a few points about the mentality you should try to approach this from:

Fake an interest in something they want to talk about, even if you don't care about it in the slightest

It's a common conversation approach to ask about someone's interests. Though usually this has a limit. If you truly aren't into one of their hobbies, you're not expected to martyr yourself and let them go on and on about it for forty minutes, just because it could score you points. Usually there's something better to discuss. Though if you're desperate to keep an interaction alive that boundary goes out the window.

If you know one of their interests, try to get them talking about it. Fake being curious. Ask follow up questions. Try to get more details. Use engaged non-verbal signals to encourage them to keep sharing. Even let them rant or monologue a bit, if you can get them going. Throw in the occasional anecdote or opinion of your own, so it doesn't seem like you're just interrogating them.

In the end you may leave thinking, "I just had to listen to them talk about audio equipment for half an hour, and I found it utterly dry and boring, but at least it ran out the clock."

Do almost all of the talking yourself

This isn't an option if you're shy or struggle with chit chat too, but if you're comfortable holding the spotlight, do most of the speaking. Normally it would be inappropriate to monopolize the conversation this way, but here anything is better than nothing.

Get in touch with your inner blabbermouth. Tell long stories. Go on about your own hobbies and opinions, as if you assume they want to hear every last detail about them. Give overly elaborate, padded updates about your life. Every so often you can stop and ask them what they think, so it seems like you're trying to have a back and forth exchange. Maybe they'll give a few words here and there, but you know you're doing 95% of the work.

Stop trying to seem the slightest bit original or interesting. Ask every boilerplate getting-to-know-you question you can think of

Overall, I think people worry too much about asking "boring" questions. It's not an instant conversation killer to casually ask someone what they do for work. At the same time, if you can come up with something fresher to say, it makes sense to go with that. However, if the conversation is hanging on for dear life, it's not the time to try to blaze new ground. If you have to ask them every dry, hackneyed small talk question in the book, do what you have to do.

Stop trying to be smooth and subtle as you grasp blindly for something that may get them talking

Drop all attempts to deftly transition between topics. If you ask if they like golf one second, then comment on their houseplants a moment later, then mention a podcast you just discovered, who cares? You're just trying to find something, anything, they may bite into.

Use more unique or quirky conversation topics

I mean the kinds of odd or fun topics that are normally fine if you're closer with someone or know you both have the same sense of humor, but would seem a bit too random or jarring with anyone you just met. You're grasping at straws here, so why not see if something works? You could share one of your more eccentric opinions or observations, tell them a goofy joke, or ask a silly hypothetical question, like, "If you could eliminate one food from the face of the earth, what would it be?"

Call attention to the strained dynamic

This can work, but I put it further down as it's not always a realistic option. Sometimes you just have to pretend the conversation is going better than it is. However, there are moments where the energy of an interaction shifts as soon as someone acknowledges it feels awkward. Everyone takes a breath, drops their guard, and makes a more honest attempt to relate to each other. Or it may open a useful dialogue about what's going on. Of course, this approach can also fall on its face and make things worse.

If you do try it, I don't mean to meekly, nervously comment on how uncomfortable things feel, then let the statement hang in the air. I mean to take charge and confidently, matter of factly comment on the dynamic, by saying something like, "It's weird. We're not totally different people, but it seems we can't settle on something to talk about" or, "Why is it whenever it's just the two of us together things feel forced?"

Lightly draw on topics that usually aren't a great idea

This is the last resort of the last resorts. In the highly unlikely scenario that you have to keep talking to someone, and no other approach has worked, you could turn to some inappropriate topics to help you think of something to say. You don't have to carry them out to an extreme degree, just enough that some words start coming out of your mouth. For example, you could start minorly complaining or oversharing about your personal or health problems, or tell them one of your controversial opinions.

Like I said, it's rare that you'll find yourself in a situation where you'll be forced to use one of these tactics. This article is mainly food for thought about what someone could do in that kind of extreme situation. But who knows, maybe one of the suggestions here will save you down the road.