How to keep an online conversation going#

You say hi. They say hi. You ask how they are. "Good u?" You say good.

And there it sits: a tiny completed transaction in which nobody learned anything, felt anything, or has the faintest idea what to type next.

This gets blamed on a lack of conversation topics. Usually it isn't. The problem is that neither person has given the other anything to work with - a detail, opinion, feeling, or story that might lead somewhere.

Give them more than a dead end#

Compare these answers:

Pretty good.

Pretty good - I finally got out for a walk after three days of rain, and now I'm pretending that counts as a major achievement.

The second answer isn't a sparkling feat of wit. It just contains things: a walk, rain, three days indoors, dubious standards of achievement. Your chat partner now has choices.

You don't need to write an autobiography every time someone asks how you are. Just include one real detail. What occupied your attention today? What annoyed you, pleased you, surprised you, made you laugh?

Use what they already gave you#

People often hand us a perfectly good subject and we drop it because we're busy thinking of a new question.

Them: I grew up near the sea, but I live about as far inland as possible now.
Dead end: Oh cool. What music do you like?
Better: Do you miss it? I grew up inland and still find the sea slightly unbelievable, like the landscape forgot to stop.

The second reply responds to what was actually said and gives something back. A conversation is not one person submitting answers while the other approves and advances the form.

Listen for the detail that seems to have some energy behind it. If someone describes six years of nursing in one sentence and their tomato plants in four, ask about the tomatoes. They are trying to tell you where the life is.

And react before changing the subject:

Them: I'm nervous about starting a new job on Monday.
You: What movies do you like?

Ask about the job. Say that first weeks are weird. Show some sign that the message arrived before marching onward.

Don't turn it into an interview#

If you ask five questions in a row without sharing anything, the other person starts to feel examined. If you answer every question with a speech and never ask one back, they start to feel like an audience.

A useful rough check: are they learning anything about you too? Not every message needs a personal story, but a conversation usually needs both people.

If you are stuck for a place to begin, here are some questions to ask a new online friend. Just don't send all of them.

Mix silly and serious#

Chats get stuck when they stay at one level too long.

If you've been trading facts, go one level deeper: not only what book they liked, but what stayed with them. If things have become relentlessly earnest, go lighter: ask about the disastrous meal, the implausible pet, the hill they are prepared to die on regarding sandwiches.

You don't have to keep pushing deeper. Move between silly and serious, large and small, the state of the world and the state of the laundry.

Remember things#

"How did the interview go?" may be only five words, but if the interview was mentioned a week ago those words carry weight.

Small details accumulate until two strangers have a shared world: recurring characters, private jokes, plants whose progress is now apparently a matter of international concern. Remembering one or two things that matter is enough.

Allow pauses#

An online conversation does not have to imitate two people trapped in a lift. Sometimes the other person is working, sleeping, cooking, caring for someone, or simply not in the mood to construct a sentence.

Don't send "??". Don't ask whether you've upset them because four hours have passed. Don't turn a pleasant chat into a new obligation they are already failing.

Some conversations are live and quick; some unfold over days. If your rhythms are different, say what yours is. "I tend to reply in the evenings" is useful information.

Know when to stop#

Conversation takes two people. No technique can make a good chat from someone who repeatedly gives you one-word answers, asks nothing, and offers nothing.

You can try once: change the subject, ask something more specific, or share something with a bit more life in it. But if you're still performing CPR on every exchange, let it go. This isn't failure. Most people will not become your people, online or anywhere else.

The point isn't to keep a conversation going at any cost. Some chats are just done.

Practice somewhere that expects effort#

I run Wusoup, a small 1-on-1 text chat community where generic messages are literally against the rules. That sounds slightly unhinged until you've received your fiftieth "hi" from someone who didn't read your profile. Then it starts to seem fairly moderate.

The rules can't manufacture chemistry, but they can remove a lot of the noise that prevents it. People are expected to read, write, listen, and bring something human to the exchange. Some chats still fizzle. That's okay too.