How to keep a text conversation going

To keep a text conversation going, give the other person something to answer. Reply to what they said, add a little of your own, and end on a question or a detail that is easy to pick up. When a topic runs out, start a new one from something real in your day, or let the chat rest and come back later. And if someone answers in one word for days, better texts will not fix it. That is covered below too.

Answer, add, ask

Conversations die when a message leaves nothing to hold on to. Compare two replies to "how was your weekend?"

Good thanks, you?

Good, thanks. We finally went to that climbing place and I can't lift my arms today. Did you get the flat sorted?

The second one answers, adds a small story and asks about them. They now have three things they could reply to. You do not need all three parts in every message, but a message with none of them is a dead end.

Answer what they asked, properly. Add one detail: what happened, how you felt, a small opinion. Ask something that follows from what they said, or leave an opening they can pick up.

Questions that get more than one word

A closed question gets a closed answer. "Good day?" gets "yeah". Change the question and the answer changes.

Three rules for questions:

• Ask about them, and about something specific. "How did the presentation go?" is better than "how are you?" because it shows you remembered.
• One question at a time. Three questions in a row reads like a form.
• Give before you ask. Offer your own answer first and the question feels like a chat, not an interview.

I've decided the best biscuit is the custard cream and I won't be taking questions. Actually I will. What's yours?

When the chat goes quiet: five ways to restart

A pause is normal. People put their phones down. When you want to pick it up again, start from something real, not "so..." or "hey".

Go back to something they said.

How did the interview go in the end? I've been wondering.

Send a thing you saw.

This sign outside the chippy made me think of you. "No fish today, the fish are fine."

Ask a small opinion.

Need a ruling. Is it too early in the year for a big coat?

Tell one short story from your day.

A man on my train just ate a whole cucumber like a banana. I have so many questions.

Suggest a plan.

We keep talking about that market. Shall we just go on Sunday?

The last one matters most. Texting is a bridge to seeing someone, and a plan gives you both something to talk about. If this is someone you like, how to ask someone out over text has the wording.

Talking to a dry texter

A dry texter answers in one word, never asks anything back, and leaves you doing all the work. Before you change how you text, work out which kind you have.

Some people are just bad at texting. They are warm in person and flat on a screen. They reply, slowly and briefly, and they turn up when you make plans. With them:

• Ask things that are easy to answer in a line.
• Move off text. A voice note, a call, or a plan to meet.
• Do not read a mood into a short reply. "ok" usually means OK.

You're clearly not a texter, which is fine. Call you at 7?

Some people are not that interested. They answer late, never start a chat and never ask about you, in person or on the phone. No technique changes this. You can say it once, lightly, and see what comes back.

I feel like I'm doing most of the talking here. All good if you're busy, just say.

If nothing changes, match their effort and put your time elsewhere. That is not a punishment. It is just not chasing.

Are you the dry one?

If people's chats with you fade, check your own side.

• "lol", "nice" and "haha yeah" end conversations. Add one sentence after them.
• When someone tells you something, ask one thing about it.
• When you are busy, say so. It keeps the thread alive.

In meetings till 5, but I want to hear all of this. Tell me tonight?

Things to talk about when you are stuck

• What they are watching, reading or listening to, and whether it is any good.
• Food: what they had, what they would never eat, the best thing they cook.
• Small plans: the weekend, a trip, what they are looking forward to.
• Something from earlier in the chat that you can follow up.
• A harmless "would you rather" or a strong opinion about nothing.
• Their people: a sibling, a flatmate, the colleague they keep mentioning.

If you are opening with someone new, how to text your crush has first messages.

Let it end well

A conversation does not have to go on all day to be a good one. Ending it yourself, warmly, is better than letting it thin out into "haha" and "yeah".

Right, I need to sleep. Good luck tomorrow, tell me how it goes.

I've got to run. This was fun, talk later?

That leaves a thread to pick up next time, which is the easiest restart there is.

What to avoid

• The interview. Question after question with nothing of your own.
• The monologue. Five messages in a row before they have answered one.
• Testing with silence. Going quiet to see whether they chase teaches you nothing true.
• "Why aren't you replying?" If you need to say something, say the thing itself.
• Serious talks by text. Arguments and big feelings go better on a call or face to face.
• Forcing it. If you have nothing to say today, that is fine. Say something tomorrow.

Doing it with Hemmingway

When you are looking at a message and cannot think what to send back, the text reply generator can get you started. Paste their message, write in rough words what you want to say or ask, and say who they are to you. It writes one short reply the way a person texts, and it uses only what you give it, so it will not invent a story or a plan for you.

Read it, change it until it sounds like you, and send it yourself. It cannot make someone interested, and a chat that only runs because a tool writes your half is not one worth keeping up. There is a free trial with no card needed.

Try HemmingwayDownload the app

Common questions

How do you keep a conversation going over text?

Answer what they said, add a detail of your own, and end with a question or an opening that is easy to reply to. Ask about specific things they have mentioned, and offer something about yourself before you ask.

What do you text when the conversation is dying?

Change the subject to something real: a follow-up on something they told you, a thing you saw today, a small opinion question or a plan to meet. Or end it warmly and start fresh tomorrow. Not every chat needs rescuing.

How do you respond to a dry texter?

Ask things that are easy to answer, and move to a call or a plan if they are better in person. If they never ask about you or start a chat, say once that you feel you are doing most of the talking, and if nothing changes, match their effort.

What are good questions to ask over text?

Open, specific ones: "what was the best bit of today?", "what did you make of the ending?", "what's taking up your week?". Questions about things they have already mentioned work best, because they show you were listening.

How do I stop being a dry texter?

Add one sentence after "lol" or "nice", ask one question about what the other person told you, and say when you are busy instead of going silent. You do not need long messages, only something the other person can answer.

Is it bad to double text?

No, not once. A second message to add something or to check in after a few days is normal. A run of messages with no reply, or a second text ten minutes after the first asking why they have not answered, is what puts people off.