How To Keep A Conversation Going On A First Date Without Sounding Like An Interview

When you sit across from someone you don't know yet, asking them a bunch of questions feels productive and keeps the silence away. It also gives you something to do while your brain runs its own background checks.
Of course, if you ask a bunch of questions, you’ll get a bunch of answers, but that is not a conversation. It's just two people taking turns to talk.
Real conversations are on the move - they go somewhere that neither person planned. One thing leads to another and before you know it you're 30 minutes deep into a story about a holiday that went massively wrong, you're both laughing and nobody's looking for the exit.

Don’t make the mistake of treating every answer as a done deal. If your date mentions they grew up in Mill Hill, don’t just file that information away and move to the next question. Because if you do, you literally walk straight past the most interesting part.
Here's what that looks like in practice:
Your date says: I grew up in Mill Hill. It was one of those places where you were never quite sure whether you lived in London or the countryside.

Interview mode: "Oh really, sounds nice - so what do you do for work?"

Conversation mode: "Did you love it growing up there or were you desperate to escape by the time you were sixteen?" 

There's a reason the follow-up matters more than the original question. When your date mentions Mill Hill, they're giving you the surface. What they don't know yet is whether you want more than that. A follow-up like "what was it like growing up there?" is essentially you saying you do - and that's the permission your date is waiting for. People generally want to talk about something real. They're just waiting for someone to show enough interest to go there.

Don’t play at being a supervisory special agent. You’re not there to profile your date. If something lands flat and your date moves past it quickly, let them move past it - don’t try to push it. Also, if a topic runs its natural course and the energy drops, don't keep dragging it along - just let it finish.

The silence arrives, someone panics, and within about three seconds they've blurted out something random just to fill the space. Usually another driver's licence question or something even weirder ‘where do you see yourself five years from now’.
A short pause in conversation is normal. It happens between friends, between people who've known each other for years, or between colleagues in the middle of a relaxed lunch. It just means the last topic reached a natural end and the next one hasn't started yet.

Your date is just sitting across the table seeing a person who paused for a second. You're experiencing it in real time with full internal access to the panic. The conversation stops, and your mind feels so empty that you can't think of a single thing to say. It happens to everyone. The easiest way to handle that is to go back to an earlier thread. Most conversations have unfinished topics - things that were mentioned and then moved past. For example ‘You mentioned earlier you were thinking about moving - is that still on the cards’. It shows you were listening, it gives the conversation somewhere to go, and you're not starting from scratch.

Try this: instead of asking your date a direct question, make a playful observation or guess instead. So rather than say ‘what kind of music do you like’, you could tell them they look like someone with a very embarrassing favourite song they'll never admit to in public. Or tell them they look like an avid board game player who absolutely refuses to admit defeat. It's low stakes, it's a bit silly, and generates a better conversation than ‘what music do you like’, or ‘do you like to play games’.
This works because your date is reacting to exactly what you said in that moment, not retrieving a stored answer, which is where actual chemistry gets a chance to appear.