The first five minutes
- How has your week actually been, not the polite version?
- Have you been to this place before, or are we both new here?
- What did you do right before this?
- What is something good that happened to you recently?
- What are you into lately that you did not expect to be into?
- Where would you be right now if you were not here?
- What is the story behind where you live now?
Stories that show who they are
Ask for stories, not summaries.
- What is something you did this year that you are proud of?
- What were you like as a teenager?
- What is the best trip you have ever taken, and what made it the best?
- Who in your life makes you laugh the most?
- What is a decision that completely changed your path?
- What are you working toward right now, outside of your job?
- What is something you are surprisingly good at?
- What is the best piece of advice you have ignored?
- What does a really good weekend look like for you?
If there is a lull
- What is your most controversial food opinion?
- What is the worst first date you have been on, minus this one so far?
- If you had to pick a theme song for your life, what would it be?
- What is the last thing you binge-watched?
- Which famous person would you want to have dinner with, and what would you ask them?
- What is the most spontaneous thing you have ever done?
- What is a skill you wish you had learned as a kid?
- What is something everyone loves that you do not get?
Getting a little more real
- What do you value most in the people you keep close?
- What does a good relationship look like to you?
- What is something you are trying to do differently than you did before?
- How do your friends describe you, and is it accurate?
- What makes you feel at home with someone?
- What is something people usually learn about you later than they should?
As the date wraps up
- What was your favorite part of tonight?
- Is there anything you wanted to ask me that you did not get to?
- What are you doing the rest of the week?
- Where would you take me if we did this again?
How to use them
Plan to ask fewer than you think. A first date might use eight or ten of these, with most of the time spent on follow-ups. The list is a safety net for pauses, not a script to get through.
Balance asking and sharing. After they answer, offer your own version, then wait. If you notice you have been talking for a while, ask a question. If they have, share something.
Some people find first dates easier when looks are out of the equation. On Hush you can talk to someone through voice notes before you ever see them, and questions from the stories section are a good way to learn whether you would even want a first date.
Questions people ask
Avoid detailed questions about exes, salary, how many children they want or anything that sounds like a checklist. They can come up naturally later. Early on they make the date feel like a screening.
Ask open questions that need a story to answer, then follow up on the specific details they mention. Sharing your own answers keeps it balanced and gives them something to ask about too.
Read them beforehand rather than bringing them along. Having three or four favorites in your head helps when there is a lull, while reading from a phone tends to make the other person feel interviewed.