How to Keep a Conversation Going

Conversations rarely die from a lack of topics. They die because someone answered a question, nobody picked the answer up, and the whole thing had to start again from cold. Do that three times and it's over. Here's the one habit that prevents it, and four ways to restart one that's already gone quiet.

The habit: go down, not sideways

When a topic slows, most people change subject. It feels helpful and it's the single most reliable way to end a conversation, because every new subject resets you both to zero.

The alternative takes less effort. Stay on what she just said and ask about that. Watch the difference:

The second one costs nothing and it gets you a real answer, usually a funny one. It also signals the thing everyone's actually hoping for — that you were listening.

Four ways down

• Ask for the detail. "Badly how?" "Which part?" "Since when?" Almost any answer has a specific inside it.
• Ask for the feeling. "Do you actually enjoy it, or is it a discipline thing?" People rarely get asked this and usually want to answer.
• Ask for the origin. "What got you into it in the first place?" Origins are stories, and stories don't stall.
• Offer yours, then hand it back. "I did that for about three weeks in January. What's your record?" Trading beats interrogating.

When it's already gone quiet

Four restarts, roughly in the order you should try them.

1. Reach backwards. "Hang on — you said earlier you'd just moved. How's that going?" The best restart is almost always something she already told you.
2. Say the quiet part. "I've completely lost my train of thought." Naming the pause defuses it; pretending it isn't happening is the only wrong move.
3. Change the temperature, not the topic. Get sillier or get more real. Both work. Staying at the same register is what makes it feel like it's winding down.
4. Ask something absurdly specific. A funny question works here precisely because it doesn't need any run-up.

Three things that quietly kill it

• "That's cool." The conversational equivalent of hanging up. If you catch yourself typing or saying it, ask a question about the thing instead.
• Answering only what was asked. One-word answers make the other person do all the work. Add a detail she didn't ask for — that's the hook she can grab.
• Being agreeable about everything. Nothing to push against, nothing to talk about. Disagree, lightly, when you actually do.

And when it should end

Some conversations are just finished, and stretching one out is worse than letting it stop. "This was fun, I'm going to head off" is a complete sentence. On a random chat you can simply move on — that's what skipping is for, and both people know it. Ending well is a skill too, and it's the one that makes starting the next one easy.

More on the first five minutes in how to talk to girls, and if you'd rather have the raw material ready, what to talk about with a girl is organised topic by topic.