First-date nerves mean you care, which is a good start. The short answer: open with easy topics they can talk about for a while, like how they spend their downtime and what they’re into lately. Add one silly question when the nerves show, take turns answering, and go one level deeper once you’re both relaxed. End on something that looks ahead.

Below is that evening in order, with questions you can borrow at each step.

Every question here comes from Lolo Cards - 4,700 conversation cards for iPhone.

First, about the nerves

You’re probably doing better than you think. In a 2018 study, strangers who had just talked to each other kept underestimating how much the other person liked them. The researchers called it the liking gap. People were so busy replaying what they said that they missed the signs that the other person was enjoying it.

So if you walk out thinking “that was awkward,” your date may well remember it differently. Bring a few good questions, listen to the answers, and let the evening do the rest.

The first ten minutes: easy topics

Start with questions that are easy to answer and easy to ask back. Nobody has to think hard, and both of you get a few minutes to settle in.

The second one does a lot of work. Whatever they’re into right now, a new show or a sourdough phase, they’ll usually light up talking about it. Ask about the details and you may have enough to talk about for the next ten minutes.

Break the tension with one silly question

If the conversation stalls, reach for something ridiculous. A silly question tells your date you’re not here to grade them.

And if you’re both obviously nervous, say so with a question. It’s hard to stay stiff after this one:

Keep it from turning into an interview

Rapid-fire questions can make a first date feel like an interview: question, short answer, new question, short answer. Two habits help a lot.

  1. Answer your own question. After they answer, give yours. In a study on getting acquainted, strangers who took turns asking and sharing liked each other more and enjoyed the talk more than pairs where one person only asked and the other only answered.
  2. Follow up before you move on. Pick one detail from their answer and ask about it. Researchers who studied question-asking found that people who asked more follow-up questions were liked more. In speed dates, they were also more likely to get a yes for a second date.

One good question with a follow-up and your own answer can carry twenty minutes.

Going one level deeper

Once you’re both laughing and the coffee is half gone, you can ask something with a little more weight. You might hold back here because you expect it to get awkward. In a set of experiments with strangers, deeper conversations turned out less awkward and more connecting than people predicted.

Take one step deeper and see how it lands. If they keep the answer short, that’s fine. Go back to something light, because you two may not want a heart-to-heart on a first date.

What to save for later

None of these are off limits forever. They just rarely help on night one: a detailed history of past relationships, salary talk, a long rant about your job. If your date brings one up, listen and gently steer back to the two of you. There will be time for the heavier stuff if there’s a second date.

End on something that looks ahead

Close with a question about what’s ahead for them. It leaves the evening on a warm note.

The last one is a gentle way to keep a door open without asking for anything. Then stop asking and tell them one thing you enjoyed about the evening. Make it specific, like the theme song they picked for themselves.

If you want more to pick from, the full list of first date questions has twenty, from easy topics to deeper ones. For someone you like but haven’t asked out yet, try these questions to ask your crush. And if you two hit it off, the getting to know you questions are good for date two.

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