Still trying to break down the walls between you? These 20 questions for newer couples and budding relationships will help you get past the surface-level stuff.
So, you guys have been dating for a while. Steady lah. You already know their standard Cai Fan order, and you’ve met the “inner circle” friends. But let’s be real: do you know what makes them tick? Most of the time, we stay in the “honeymoon phase” bubble because going deeper feels a bit… paiseh. Because we’re shy (it’s true).
But if you want a relationship that’s more than just a “situationship” or a BTO business arrangement, then you might be in the market for some meaningful questions to get to know who you’re really dating.
Emotional intimacy sounds like something out of a cheesy Mediacorp drama, but, quite often, it’s actually the “secret sauce”. It’s about building a foundation where you understand each other’s inner worlds. And without getting to the ‘heart’ of the relationship, you’re just two people sharing a Grab/Comfort-taxi ride through life.
Maybe that’s a bit harsh, but hey. We’re here to fix that.
Here are 20 questions worth asking. But first, a quick word on how to actually bring them up.
Explore this page
- How to ask these questions
- Building trust
- Questions about where you’re both headed
- Values and growth
- How you love and how you want to be loved
- Conflict handling
How to ask these (without killing da vibe)
I mean, nobody wants to sit across from their partner at a cafe and go “So, question number one…” like it’s a BTO appointment or a listening compre. These conversations work better when they come up on their own, not when you’ve scheduled a Serious Talk™.
Perhaps bring one up over supper. On the MRT home after a long day. During one of those aimless weekend drives where you’re both too full to do anything else. If your partner is stressed about work or half-asleep on the couch, well…. maybe don’t pick that moment to ask about their deepest fears.
A few things that help:
Go first. If you want your partner to open up, we’d suggest going first, or in turns. Because, eh, come on, vulnerability is a two-way street.
Don’t machine-gun through the list. Pick three or four per conversation, tops. If a question leads somewhere interesting, do follow it. You’re not trying to speedrun getting to know each other.
Let them think. Some people need a minute. They might just be taking the question seriously. Don’t rush to fill the gap.
Don’t weaponise what you hear. This should go without saying, but if your partner shares something personal with you, bringing it up during your next argument is a sure-fire way to make sure they never open up again. Oops.
Be okay with “I don’t know.” Not everyone has their answer figured out. Come back to it another time.
Okay, on to the questions:
1. Building trust
Trust between couples is knowing that your partner has your back when things are rough. This lets you know you have someone in to corner you can rely on. Use these and similar questions to build trust and help each other feel secure.
- What’s one thing you’re sometimes shy to tell people, but you feel safe enough to tell me?
- If I’m having a massive breakdown over work or family, do you think you’re the type to give me a ‘tough love’ reality check or just buy me my favourite BBT (bubble tea) and let me vent?
- Is there a line you need drawn in relationships that you’ve struggled to communicate before?
- When you’re feeling insecure, what’s the one thing I can do to make you feel safe and protected again?
2. Questions about where you’re both headed
In Singapore, life milestones come with deadlines. BTO balloting, career progression, and even family expectations about when you should be doing what by what age. If you’re both heading in different directions, better to find out now than two years in, when one of you brings it up at CNY dinner.
- The Ultimate Hypothetical: If we finally get invited to select a BTO flat, but it’s in a super “ulu” area (like Tengah or Tuas), do we take it and “make it work,” or do we skip and wait another three years for a mature estate?
- If one of us gets an amazing job offer in London or New York, are we the “let’s go together” type or the “long distance is okay” type?
- How much does your family’s opinion weigh on your life decisions? If they “disapprove” of a choice we make, do we listen or do we just bo bian and carry on?
- What’s your “retirement dream”? Staying in a cozy HDB near your grandkids, or selling everything to live in a campervan overseas? What about FIRE?
3. Values and growth
Experiences growing up play an important role in shaping your partner’s values and personality. These questions touch on significant events and invite conversations that could uncover traits and beliefs that you may not have expected – despite how much you think you know them.
- Growing up in the SG school system, do you feel like you were “pushed” too hard, or did that pressure make you who you are today?
- What’s a “non-negotiable” for you in a household? (e.g., must have a helper, must do our own laundry, or do we take turns doing various chores, etc.).
- What’s the biggest lesson you took away from a past relationship?
- If we suddenly had an extra $50k in our joint savings, are we investing it, reno-ing the house, or blowing it on a ‘once-in-a-lifetime’ trip?
4. How you love, and how you want to be loved
We’ve seen that plenty of couples run into trouble not because they don’t care about each other, but because they show it in ways the other person doesn’t pick up on. So, if you can figure this out early, you’ll spare yourselves a lot of unnecessary frustration. Use these questions to understand how to pay just the right kind of attention.
- Do you find it easier to show affection or receive it?
- If you’re feeling neglected, would you tell me straight, or would you remain ‘low-key’ and wait for me to notice?
- What’s the most meaningful date we’ve had so far?
- Do you prefer PDA (Public Displays of Affection) or are you a strictly ‘home-only’ affectionate person?
5. Conflict handling
“We haven’t even had a proper argument yet, why bring it up?” Well, firstly, because you will eventually (sorry), and, secondly, how you both handle it will matter more than whatever you were arguing about in the first place. Couples who figure out the questions to these question early may not necessarily fight less often, but – and here’s the key – fight can become less serious or heated.
- When we have our first “big” argument, what’s the ground rule? Do we talk it out or do we need a cool-down period to go ‘stone’ (decompress) somewhere for an hour first?
- Is there anything about us that’s been bugging you, even a little, that you haven’t said yet?
- How did your family deal with arguments? Do you think that shaped how you handle conflict now?
- After a disagreement, what can I do afterwards? Do you need space? A check-in text/Whatsapp? Reassurance that we’re okay?
How to use this list
Err, like we mentioned, don’t treat this like a TYS (Ten Year Series) exam, of course. You definitely don’t need to finish it. Maybe just pick one “category” per date? If you’re stuck in traffic on the PIE or waiting for your food at Newton Food Centre, just pull one out.
And if the conversation gets a bit heavy, then hey, it’s okay to pause and go get some ice cream. We promise.
with Love,
The Dateideas Team
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Frequently asked questions
When is the right time to ask meaningful questions for couples?
A slow Sunday walk, a long car ride, or any moment that isn’t a rushed weeknight after work. New relationship questions land better when neither of you is tired or on a clock.
What’s the difference between fun questions and deep questions to ask your partner?
Fun questions to ask your partner (“most likely to” scenarios, hypothetical questions for couples) keep things playful and low-stakes. Deep questions for couples push into actual territory: values, fears, how they handle a fight.
Are emotional intimacy questions different from intimate questions for couples?
They overlap, but emotional intimacy questions are specifically about understanding how your partner feels and processes, while intimate questions for couples can include anything that requires real vulnerability. Asking someone what they need when they’re struggling counts as both.
Do heart to heart questions work if you’re still new?
Yes, and arguably more so, because you’re still building the foundation. Questions to ask your crush or someone you’ve just started seeing don’t have to be heavy; even asking what they regret, for example, tells you more about a person than six months of surface-level dates.
