What questions should you ask on a first date?
Ask things with more than one good answer, follow up on what you hear, and leave their body and history alone.
A first date is not an interview. Use these as a way in, not a script: the best question is usually a follow-up to whatever they just said, and "how did that happen?" beats moving on to question eleven. Answer your own questions too.
Easy openers
What has been the best part of your week so far?
What are you reading, watching or listening to at the moment?
What would you do with a free Saturday and nothing planned?
What did you do recently that you would happily do again?
What is something you are unexpectedly good at?
What do you usually order somewhere like this?
Where would you take a friend who was visiting for the first time?
What have you been meaning to try for ages?
Values, gently
What do you care about more than most people around you seem to?
What does being a good friend look like to you?
What is something you have changed your mind about in the last few years?
Who do you call when something goes wrong?
What would you like more of in your life right now?
What are you proud of that people rarely notice?
Is there a group, a cause or a community you actually show up for?
Is there a rule you live by that you have never actually said out loud?
What you are both looking for
What made you want to meet up?
What does a good week with someone you are seeing look like to you?
Are you looking for something in particular right now, or seeing what happens?
How much contact do you like between dates?
What matters most to you in how someone treats you?
Is there anything that makes dating easier or harder for you?
What is something you will not compromise on?
Just for fun
What opinion would you defend for far longer than it deserves?
Which fictional place would you move to, and what would you do there?
If you could be excellent at one thing overnight, what would it be?
What is the best thing you have ever found secondhand?
What song would you pick at karaoke, and would you actually sing it?
Which hobby did you drop that you would happily pick up again?
What would your perfect ordinary day look like, start to finish?
What is the worst advice anyone has ever given you?
Questions not to ask a trans or non-binary person
The rule is simple: their body, their medical history and their past are theirs to bring up. It holds on a t4t date, and it holds if you are trans yourself.
"What's your real name?" or "What was your name before?" Their name is the one they gave you; the old one is a deadname.
Anything about surgery, hormones or their body, including as a joke.
"What were you assigned at birth?" It changes nothing about the date and tells them you are sorting them.
"Can I see a photo from before?"
"But which are you really?", in any wording.
"How does sex work for you?" Never as small talk.
"When did you know?" It sounds gentle, and it asks for the whole story on day one.
"Would dating you make me gay?" Your label is yours to work out.
Asked one already? Say sorry once and change the subject. On the receiving end? A match keeps asking invasive questions has lines that work.
Pronouns are the exception
If their pronouns are not on their profile, asking once is fine: "What pronouns do you use?" Then use them, and get back to the karaoke question.