How to keep a conversation going with a new friend

Science · by Simone Rainieri · 8 min read

The most reliable way to keep a conversation going with a new friend is to ask follow-up questions about what they just said, go slightly deeper than feels polite, and end each exchange with something still open. That is not folk wisdom. Each part of it has been tested in controlled studies of real conversations, and the effects are large enough that researchers were surprised.

What makes early friendship conversations hard is not a shortage of topics. It is that both people are running a quiet risk calculation, wondering whether interest will be returned, and defaulting to safe material that gives the other person nothing to grab onto. The fixes below attack that directly.

Ask more questions, especially follow-ups

In 2017, a Harvard team led by Karen Huang analyzed live conversations between strangers and found something blunt: people who ask more questions are better liked by their conversation partners, and the effect is strongest for follow-up questions, the kind that build on what the other person just said ([Huang et al., Journal of Personality and Social Psychology](https://www.hbs.edu/faculty/Pages/item.aspx?num=52115)). The proposed mechanism is simple. Questions invite self-disclosure, self-disclosure feels good, and the person doing the disclosing credits that good feeling to you.

The same research found that people do not anticipate this. We assume talking well means saying interesting things. In practice, the person asking is the one being remembered warmly.

Follow-ups beat topic changes because they prove you were listening. If your new friend mentions they just switched jobs, the weak move is answering with your own job. The strong move is asking what finally tipped them into leaving. One is a parallel monologue. The other is a conversation.

Go deeper than feels safe

Small talk stalls because it is designed to. It exchanges no information anyone can respond to. Michael Kardas, Amit Kumar, and Nicholas Epley ran a series of experiments where strangers were assigned genuinely deep questions, things like what they were grateful for or when they had last cried. Participants predicted these conversations would be awkward. They were wrong by a wide margin: the deep conversations felt less awkward and produced more connection and happiness than the shallow ones, and afterwards participants said they preferred them ([Kardas, Kumar and Epley, 2021](https://pubmed.ncbi.nlm.nih.gov/34591541/)).

The researchers call the barrier miscalibrated expectations. We underestimate how interested other people are in our real answers, so we keep serving the weather. With a new friend, the practical version is this: when you have a choice between the safe answer and the true one, the true one is nearly always the better conversational bet.

You do not need to open with childhood wounds. Depth ratchets. Offer one notch more honesty than the current level, and let them match it.

End on an open loop, not a closed door

Conversations with new friends rarely die mid-sentence. They die between sessions, when a chat ends so neatly there is no reason to start again. The fix is to leave threads deliberately unfinished. Mention the thing you will find out by Thursday. Ask a question they will need to think about. Promise the photo you have to dig up. Each open loop is a licensed excuse for the next message, and early friendships run on licensed excuses.

This matters because the volume required is higher than most people think. Jeffrey Hall at the University of Kansas tracked how friendships form and found it takes roughly 50 hours together to move from acquaintance to casual friend, about 90 to become a real friend, and over 200 for a close one ([University of Kansas](https://news.ku.edu/news/article/2018/03/06/study-reveals-number-hours-it-takes-make-friend)). Nobody accumulates 50 hours through conversations that keep politely concluding.

What kills conversations with new friends

Three patterns do most of the damage. Interview mode: all questions, no disclosure, which starts to feel like an audit. Mirror mode: responding to every story with your own matching story, which Huang's data suggests reads as self-focus even when it is meant as empathy. And scheduling mode: turning every exchange into logistics about when to next talk, which is the conversational equivalent of only ever discussing the relationship.

There is also a slower killer, the message that requires too much. A four-paragraph reply is a gift that feels like homework. Short and frequent beats long and rare while a friendship is still finding its rhythm.

When the medium is the problem

Some stalls have nothing to do with skill. Text strips out tone, timing, and shared experience, and some pairs who are awkward in chat are easy on a call. Others need something to react to. This is why doing an activity together mid-conversation works so well: a film, a playlist, a game generates its own material, and reactions to a third thing are lower-stakes than statements about yourself. It is the logic behind Vairi's in-chat prompt games and synced co-watching, which exist precisely because two well-matched people can still run out of road when the only input is a blinking cursor. We wrote more about that in [our guide to icebreaker games online](https://vairi.app/journal/icebreaker-games-to-play-online-with-someone-new).

A week-one playbook for a brand new friendship

Theory is nice; here is what the first week looks like in practice. Day one, after you meet or match, send something specific within a few hours: not how are you, but a reference to the thing you actually talked about. Days two and three, aim for one exchange a day of a few messages each, ending on an open loop rather than a full stop. By day four or five, change the medium once. Suggest a voice call, a shared playlist, or watching something at the same time. The pairs that survive past week one are almost always the ones that made at least one medium jump early, because each new channel adds a dimension the last one was missing.

Notice what is not in that playbook: daily good morning texts, hour-long question marathons, or forced vulnerability. Intensity is not the goal. Rhythm is.

And expect a lull around week two or three. Almost every new friendship hits one once the introductory material runs out and before shared history exists to replace it. The lull is not rejection. It is the gap between the conversations you were given, about jobs and origins, and the conversations you have to build, about the things happening in both your lives now. The friendships that last are the ones where somebody pushes through the gap with a low-effort, specific message rather than waiting for the other person to resolve it.

One more distinction earns its keep here: the difference between a conversation that is stalling and one that is finished. A stalling conversation still has warmth in it, slow replies that are nonetheless specific, questions that come back eventually. A finished one goes generic: replies shrink to reactions, questions stop arriving at all, and the effort balance tips fully to one side for weeks. The first deserves a format change and some patience. The second deserves a graceful exit, because conversational skill cannot manufacture interest that is not there, and the hours you would spend forcing it belong to a better match.

Knowing which situation you are in is half the craft. The other half, everything above, only applies to the first.

Key takeaways

Follow-up questions are the single most reliable likability tool in the conversation literature, and most people underuse them. Deep questions outperform small talk by a wide margin in controlled experiments, despite near-universal predictions of awkwardness. Friendship takes roughly 50 hours to start and 200 to deepen, so leave open loops that make the next conversation easy to begin. When chat stalls, change the medium before you blame the match.

Common questions

How do I keep a conversation going over text without being annoying? Send shorter messages more often, anchored to something specific they said. One good follow-up question beats three paragraphs. If replies are warm but slow, match their pace rather than flooding the gap.

What if every conversation feels one-sided? Track the question balance for a week. If you are asking everything, name it lightly or pull back and see what happens. Some people are poor initiators but good responders; some are just not investing. The pattern over weeks, not any single exchange, tells you which. Our piece on [one-sided friendships](https://vairi.app/journal/signs-a-friendship-is-one-sided) goes deeper.

Is it normal to run out of things to say with someone I like? Completely. Depleted topics are a signal to change format, not a verdict on compatibility. Watch something together, play a prompt game, or take a walk on a call. Shared input creates new material that neither of you had alone.

Related reading: [How long does it take to make a close friend as an adult?](https://vairi.app/journal/how-long-does-it-take-to-make-a-close-friend-adult), [Why making friends as an adult feels so awkward](https://vairi.app/journal/why-making-friends-as-an-adult-feels-so-awkward), [How to make friends online that actually become real friends](https://vairi.app/journal/how-to-make-friends-online)