What to talk about on a short first date

What a short date is for

In 20 minutes you cannot learn everything about a person, and you do not need to. You are finding out what it is like to talk to them. Do they listen? Are they curious? Do you laugh? Does the time go quickly? Good topics are simply the ones that let you find those things out. That is why “what do you do?” so often falls flat: it produces a job title, and a job title tells you very little about what someone is like to be around.

Openers that work

The first minute sets the tone. Skip “so, tell me about yourself.” Try something small and answerable instead.

• “What has been the best part of your week so far?”
• “What were you up to right before this?”
• “Is this your first video date, or are you a veteran?”
• “Whereabouts are you? What do you like about living there?”

None of these is clever, and that is the point. An opener only has to be easy to answer. The interesting part comes from what you do with the answer.

Questions with a story behind them

The best questions cannot be answered with one word, and they invite a small story rather than a fact.

• “What is something you have got into lately?”
• “What would you do with a completely free Saturday?”
• “What is the best meal you have had this year?”
• “What is a place you keep meaning to go back to?”
• “What did you want to be when you were ten?”
• “Who is the funniest person you know?”
• “What is something you changed your mind about?”
• “What are you looking forward to in the next few months?”

You only need two or three of these. A conversation that is going well will not come back to your list.

Follow up instead of moving on

An easy mistake on a short date is treating questions as a checklist. Someone mentions they spent the weekend helping their brother move, and the reply is “cool, and what do you do for work?” The better move is usually to stay where you are: “Are you two close?” or “Are you the organized one or the one carrying the sofa?”

A simple rule: ask at least one follow-up before you change the subject. It shows you were listening, and it is where conversations stop being small talk.

Give something back

Questions alone do not make a conversation. If you ask about their free Saturday and they describe a long hike and a late breakfast, answer the same question yourself without waiting to be asked. Roughly equal airtime is a good sign, and it is something both of you can steer.

If you tend to talk a lot when nervous, pause after you have made your point and hand it over. If you tend to go quiet, decide in advance on one or two things about yourself that you are happy to volunteer.

What to skip

• The résumé. Job, degree, where you grew up, in order. It is accurate and it is dull. Let those facts come out along the way.
• Exes and dating history. How the last relationship ended is a later conversation, and complaining about other dates makes people wonder what you will say about this one.
• The interrogation. “What are you looking for?” and “where do you see this going?” are fair questions eventually. In the first 20 minutes they feel like a screening.
• Hot-button debates. You do not have to hide what you believe. But a short first conversation is a poor place to argue it out.
• Heavy disclosures. Being open is good. Handing a stranger something very painful in the first ten minutes asks more of them than a first conversation can carry.
• Running commentary on the date. “This is awkward, isn’t it?” once, with a smile, is fine. As a refrain it becomes true.

One exception is worth making. If something is a real dealbreaker for you, and knowing it would save you both time, it is kind to say it simply and early.

When it goes quiet

A pause usually feels longer than it is, and video adds its own small delays. Let a beat of silence be. If it stretches, go back to something they said earlier: “You mentioned your sister’s restaurant. What kind of food?” Returning to an earlier thread is the easiest restart there is, and it shows you were paying attention.

You can also say what is on your mind about the moment itself: “I always go blank about now. Ask me something.” People are often relieved.

The last two minutes

Do not start a big new topic at the end. Close a loop instead: mention the thing you enjoyed hearing about, and say goodbye warmly. If you want to see them again, say so, or let the format do it for you. Our guide to a 20-minute video first date has more on ending well, and on the setup that makes the talking easier.

Magnetic is built around conversations this length: a Magnetic Night is one or two 20-minute video dates with no messaging beforehand, so nothing has been said yet when you sit down.