What are good questions to ask on a first date in Singapore?

The best first date questions in Singapore go beyond 'what do you do' and 'where did you study'. Instead of asking about hobbies in general, ask how often she actually practises them or whether she has taken any classes. Instead of asking where she has travelled, ask where she would go tomorrow if she had all the time and money in the world. The goal is not to impress her with clever questions — it is to be genuinely curious about who she is, not just what she does.

What should men talk about on a first date in Singapore?

In Singapore, first dates often default to work, school, and mutual connections. Better conversation areas include how she actually spends her time (beyond just listing hobbies), what genuinely excites her about life, what shaped who she is today, and what she values or would do if she did not have to think about money and CPF. The key is curiosity over performance — respond to what she says, share your own perspective, and let the conversation lead rather than following a script.

How do I avoid awkward silences on a first date?

Awkward silences on first dates usually happen when both people are running out of surface-level questions and neither has gone deeper. The fix is not more questions — it is better follow-up. When she answers, respond with your own thought or story before asking the next question. This creates a conversation rather than an interview. On a first date in Singapore, going from 'where have you travelled' to 'where would you go tomorrow if you could go anywhere' immediately opens up more interesting, imaginative conversation.

Why does conversation on my first dates always stall?

If your first date conversations in Singapore are not going anywhere, it is usually one of three things: you are asking closed questions that have one-word answers, you are interviewing rather than conversing (question, answer, question, answer without sharing your own perspective), or you are keeping everything surface-level out of fear of going deeper. A dating coach can help you identify specifically what is happening in your conversations and what to change.

What are the biggest first date mistakes men make in Singapore?

The most common first date mistakes for men in Singapore are: spending most of the date talking about work, asking biographical questions (school, job, family) rather than getting to know her as a person, trying to impress instead of being curious, asking questions without sharing anything about yourself, and not making it clear at the end that you want to see her again. These are all fixable — a dating coach can identify which one is happening in your specific case.

What is the best way to prepare for a first date in Singapore?

The best preparation for a first date in Singapore is not memorising a list of questions — it is going in with genuine curiosity about who she is and being willing to share something real about yourself in return. Know the four areas worth exploring: how she spends her time, what genuinely excites her, what shaped her, and what she values. Then let the conversation lead rather than sticking to a script. If you want personalised preparation, portmanteau's Singles Mixer and First Date Intensive coaches you on conversation, presence, and what to wear — tailored to your specific situation.

What to Talk About on a First Date (non-boring)

In work-focused Singapore, it’s very easy to get caught up asking about / talking about work. Work does take up so much of our lives, and it’s so easy to fall into that trap simply because there’s so much to talk about. “How many days do you work from home?” “How long have you been here?” etc. are all very valid questions, but surely neither of you want to spend your date talking about work.

I believe that how we approach dates - especially first dates - should be to learn about the other person with curiosity and intentionality. So if you’re googling "What are some non-boring topics to talk about on a dinner date?" or “Good questions to ask on a first date”, chances are, you’re on the right track.

But following a list of so-called “good questions” runs the risk of the date feeling performative. Plus, it’ll probably be weird if you suddenly jumped in with a “Do you have a favourite childhood memory that still makes you smile?” if the conversation was never leading in that direction.

Here is a list of not questions, but things that you can learn about her. These are going to be topics you will be familiar with, but with better, more intentional questions.

1: how she spends her time

Instead of just “What hobbies do you have?”, or “How do you spend your free time?” try:

“How often do you practise your hobby?”

“Have you taken any classes?”

“Is there anything in Singapore you always wanted to do but never got around to?” Why?”

These are far more specific, and make the conversation a lot easier. Notice that beyond the surface-level conversation of “what her hobbies are”, it goes beyond and explores how she actually spends her time.

2: what excites her

It’s really easy to ask “Where are you travelling to next?” or “Where did you go to recently?” and you’ll probably get “Japan” (to which you might respond “Who did you go with?” or “Oh me too!”).

But on top of that, a fun one might be:

“If you had all the time and money in the world, where would you go tomorrow? Why?"

This expands your understanding of her beyond what she’s just done / what her plans are, but what she really wants to do and her dream trip(s). This makes for a much more imaginative, fun conversation where you can chime in with your own dream trip, your constraints etc.

3: what / who shaped her

This might be controversial, but especially in Singapore, where everyone knows everyone, it’s really easy to fall back on “What school did you go to?” and think about whether you know anyone from there. But is the question really about the school? Isn’t it:

“How do school shape you?”

“How did your school affect the way you see life?”

This opens her up to think, reflect and share her experiences, rather than leaving you to your own assumptions about whichever school she went to, if any.

4: what she values

I don’t think we talk about our dreams enough in Singapore. The cost of living is high, the pressure to BTO is intense, the need to have a job that pays CPF is pressing.

Dates don’t have to be confined to our reality. They are a sneak peek into someone else’s world - not just their visible world, but their invisible, inner world.

What would you do for free if you didn't have to work and you had all the time and money?

This might lead to other conversations about deeper-held values like responsibility, freedom etc.

remember: it’s not just about what you ask, but how you ask

It's really important to go with the flow.

You don't want to come across robotic, or like an interviewer.

Instead of question > answer > question > answer (which may be interrogative) - respond, share your thoughts / your own story, and see where she takes you.

most importantly: you’re not trying to impress her.

Remember: this is not a script or a list that you should keep referring to. It’s not about even about the quality of the questions; it’s about being curious about her, and genuinely getting to learn about her as a person. That’s more powerful than any list of questions you might ever have.

If you think you’re already asking good questions at first dates / singles events but they don’t seem to go any further, let’s figure out why. My dating deep dive explores where you are, what’s standing in your way, and targets exactly what you need to change for you to reach your dating goals.

→ Free Download: sample proposal for dating deep dive

Or, if you'd like a shorter, punchier intervention, my sprint prepares you for your next first date / singles mixer with practice, a plan, and a personal shopping session or profile audit.

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questions to ask on a first date that aren’t about work: the definitive guide

1: how she spends her time

2: what excites her

3: what / who shaped her

4: what she values

remember: it’s not just about what you ask, but how you ask

most importantly: you’re not trying to impress her.

about the author

portmanteau

questions to ask on a first date that aren’t about work: the definitive guide

1: how she spends her time

2: what excites her

3: what / who shaped her

4: what she values

remember: it’s not just about what you ask, but how you ask

most importantly: you’re not trying to impress her.

about the author

non-boring, non-awkward first date ideas in singapore

best dating apps in singapore for a serious relationship: an honest comparison

portmanteau