How to Keep a Conversation Going
Entry No. 213 ·
By The IF Team
To keep a conversation going, ask the question after the question. Follow up on what the other person just said instead of changing the subject, share something of your own in return, and go one layer deeper than small talk — from “What do you do?” to “What do you love about it?”. Over text, give them something specific to answer; in person, let a small silence be. And end while it is still good: a conversation that stops on a high is far easier to restart than one that has run out of road.
If your mind goes blank the moment you are talking to someone you like, nothing is wrong with you. Wanting a conversation to go well is exactly what makes it hard: part of your attention goes on the person and part on monitoring yourself. The habits below shift that attention back where it belongs, which is also what makes you good company.
Good conversation is often where a crush begins: the colleague you could talk to for hours, the friend’s flatmate who made a party fly by. Sometimes the person you most want to keep talking to is someone you cannot pursue right now. IF was made for exactly that kind of feeling: it lets you be truthful about it, whether you are single or attached and whoever it is about, and keeps what began in real life safe until the moment comes to act on it.
Ask the question after the question
The single most useful conversational habit is the follow-up question. In a set of Harvard studies, people who asked more questions — especially follow-up questions — were liked more by the people they talked to, because follow-ups show you were actually listening. The researchers also found that people underestimate this: they do not expect asking questions to make them more likeable, so they ask too few.
The difference between a switch and a follow-up is easy to hear:
- They say: “I’ve just got back from Lisbon.” A switch: “Nice. I’m going to Rome in June.” A follow-up: “What was the best thing you ate there?”
- They say: “Work’s been mad this week.” A switch: “Same.” A follow-up: “Mad good or mad awful?”
- They say: “I’ve started climbing.” A switch: “I prefer running.” A follow-up: “What got you into it?”
A follow-up does not have to be clever. It just has to prove that the last thing they said landed somewhere.
Go one layer deeper than feels natural
Small talk is a doorway, not a room. Most of us linger in the doorway because we assume the other person would rather keep things light. They usually would not. In a series of experiments with more than a thousand participants, people consistently expected deep conversations with strangers to be more awkward and less enjoyable than they turned out to be, and underestimated how interested their partner would be in going deeper.
You do not need to leap to “What’s your greatest fear?”. Just take each topic one step further:
- From what they do to why they chose it, or what they would do instead.
- From where they grew up to what they miss about it.
- From what they did at the weekend to the best part of it.
- From a film they liked to the moment that stayed with them.
Share something back
Questions alone turn a conversation into an interview. The rhythm that builds closeness is give and take: they tell you something, you ask about it, then you offer something of your own at roughly the same depth. If they mention missing their grandmother’s cooking, a story about your own family table invites them further in; a joke about the canteen pulls them back out.
Match the depth rather than raising the stakes. Answering a light story with your deepest secret is as jarring as answering a vulnerable one with a pun.
Over text: give them something to hold
Text conversations die for one reason above all: a message gives the other person nothing to reply to. “Haha nice” is a full stop. A good text answers what they said, adds a little of you and leaves a hook:
- Answer, add, ask: “Ha, that’s brilliant. My flatmate tried the same thing and set off the smoke alarm. Did yours actually rise?”
- Pick up an old thread: “Wait, you never told me how the interview went.”
- Send something they can react to: a photo, a song or a place you think they would like.
- If the conversation is flagging, suggest moving it somewhere better: a call, or a coffee.
If the other person keeps replying in two words, they may simply be a dry texter who comes alive in person. Starting from nothing? What to text your crush is the place for first messages, and when you want a conversation to turn playful, flirting over text takes it from there.
In person: let silence do some of the work
A pause feels three times longer to the person worrying about it. Often the other person is simply thinking. Let a beat pass before you rush to fill it, and when you do speak, a few reliable moves keep things flowing:
- Reach back: “Going back to what you said about your brother’s band…”
- Notice something around you: the music, the food, the people at the next table.
- Ask for an opinion rather than a fact: opinions invite stories.
- Admit the moment: “I’ve completely lost my train of thought” is endearing, not fatal.
If you are quieter by nature, none of this requires you to become a performer. Listening well is half of good conversation, and dating as an introvert has more on dating in a way that suits you.
When it keeps dying, whatever you do
Sometimes a conversation will not catch, and it is not your fault. If they answer without asking anything back, check their phone, or give the same flat reply however you approach a topic, they may be tired, distracted or simply not feeling it. One stalled conversation is not a verdict. A string of them is information. And if the conversation flowed on a screen but stalled in person, great chemistry over text but not in person explains why that happens so often.
End on a high
The final skill is knowing when to stop. Researchers who asked people about their real conversations found that only about 2 per cent ended when both people wanted them to, and people were poor at guessing when the other person was ready to finish. So leave at a good moment rather than waiting for the energy to run out: “I have to head off, but I really want to hear the end of the Lisbon story” is an invitation to talk again.
Where IF fits: the conversation you are not having yet
What do you do with the best conversation you have had in months, when the person on the other side of it is going home to someone else? You swapped stories until the lights came up, and then you both left as if nothing had been said.
This is where IF comes in. It is for feelings that begin in real life, often in a conversation exactly like that one, and it lets you say them honestly, regardless of who is with whom, so they can be acted on when the time is right.
The best exit line in this guide works here too: end on a high, and leave a hook. An IF gives you 250 characters to do it: “We never finished the Lisbon story, and I’ve thought about that conversation more than I should. Whenever we’re able to, I want the ending, over dinner ideally.” It goes sealed, and no conversation follows on IF while either of you is with someone; until you are both single, it simply keeps the thread.
Your name and your words stay held back until it opens, though anyone already using IF might be told that one is waiting. If they have not joined, what reaches them depends on what you used: an email address they gave you leads to one short invitation, while a number or Instagram handle leads to nothing, and the IF holds on in case they sign up. The simpler case is when you are both single and they have IF: a Like, once accepted, puts you straight back into follow-up questions.
There is no fee for the first IF you send. Every good conversation ends with a reason to have the next one, so make this the reason.
Questions people ask
How do you keep a conversation going with your crush over text?
Answer what they said, add something of your own and end with an easy, specific question. Pick up threads from earlier conversations, and if it is flagging, suggest a call or a meet-up rather than forcing more messages.
What do you talk about when the conversation dies?
Go back to something they mentioned earlier, ask for an opinion, or comment on something around you. Opinions and stories restart a conversation more easily than new factual questions.
How do you avoid awkward silences on a date?
You do not have to avoid them completely; short pauses are normal. Choose a setting with something to react to — food, a walk, an exhibition — and keep a couple of open-ended threads in your back pocket.
How can you tell if someone wants to keep talking?
They ask you questions back, build on what you say and stay focused on you. Short answers, glances at the time and no questions in return usually mean it is a good moment to wrap up warmly.
Ask the question after the question, share a little of yourself and leave while it is still good. And if your best conversation lately was with someone you cannot pursue yet, keep your place with an IF.