How to start meaningful conversations on dating apps

Relate & Date: Overcome dating conversation struggles with tips for meaningful connections

A woman lying on bed and a man sitting on a sofa check their online dating messages on their smartphone. (Photo: Getty Images)
A woman lying on bed and a man sitting on a sofa check their online dating messages on their smartphone. (Photo: Getty Images)

In the realm of dating apps, the exchange of generic pleasantries often leaves users feeling stuck. So imagine a conversation going like this:

“Hi, how are you?”

“Good, how are you?”

“Good too!”


If the above scenario seems familiar to you, you’re probably an old hat when it comes to hitting a brick wall in dating app conversations. With nearly 3 in 10 people in Singapore turning to dating apps like Tinder, Bumble and Coffee Meets Bagel to find love, it’s evident that these platforms dominate the modern dating scene – and pretty much how most people meet potential romantic partners these days. While technology has made it easier to meet new people, the quality of conversations on these apps often falls short.

If you’re one of those who struggle to have interesting or meaningful conversations with people you match with on dating apps, read on for useful tips on how to spark meaningful connections and get those conversations flowing.

Setting the right tone

Dating app users face a barrage of potential matches every day. To stand out, it’s crucial to transcend clichéd greetings. Start with a genuine compliment that showcases your interest in their passions. For instance, if their profile highlights a love for local cuisine, you could express your enthusiasm for exploring hawker centres together. Another way to stand out from the sea of humdrum greetings could be to open with light-hearted humour. For example, something straightforward yet tongue-in-cheek like, “If your life were a book, what would the title be? Mine would be 'Overthinking Opening Messages'”.

Best case scenario? The person laughs and responds. You’ve shown you have a good sense of humour and the conversation flows much more easily from there.

Worst case scenario? The person doesn’t reply and you know you dodged a bullet – no humourless dates, thanks!

Happy young couple smile and talking together with paper cup telephone. (Photo: Getty Images)
Happy young couple smile and talking together with paper cup telephone. (Photo: Getty Images)

Crafting memorable conversations

Once you’ve reeled them in and gotten them interested in chatting more, keep the momentum going! Ask open-ended questions about their weekend plans or any favourite secret city spots – and be sure to share your own opinions and experiences. Sharing personal experiences is a great way to foster a deeper connection.

While texting the other person can be enjoyable, most dating and relationships experts recommend not spending too much online and to make plans to meet in person as soon as possible. That’s because it can be easy for a connection to fizzle out if conversations are conducted entirely over text or even voice calls. It’s important to meet the person IRL (in real life) to see if the chemistry translates to the real world.

Topics to talk about on a first date

While meeting your date in real life can be nerve-wracking, try to relax and remember – the other person probably shares those jitters! One way to help you feel more at ease is to pick a comfortable setting like a familiar restaurant, a favourite park or even a cozy cafe with a laid-back ambience.

When it comes to keeping the conversation animated, remember to keep it lighthearted and fun. You are on a date, not a job interview. Ask open-ended questions and discuss your shared interests, whether it’s a love for art, music or the great outdoors. If you both share a passion for travelling, share travel anecdotes, discuss your favourite destinations and the cultural experiences that left a lasting impression. Travel stories often evoke a sense of adventure and wonder, and can help you learn more about the other person.

Navigating taboo topics

Many dating articles often advise steering clear from politics, religion or past relationships. Contrary to common advice, addressing taboo subjects can be beneficial and transformative if done artfully.

When we avoid taboo topics, we inadvertently present a curated version of ourselves, hiding our true beliefs and passions. Embracing these conversations showcases authenticity. Sharing our thoughts on religion, politics or life philosophies allows us to be vulnerable and honest, establishing a foundation of trust. Authenticity is magnetic; it draws people in and forms the basis for more meaningful relationships.

Taboo topics also serve as a litmus test for compatibility. While certain differences can be enriching, they can also be potential sources of conflict in a relationship. By addressing these topics early on, you can identify fundamental differences in beliefs or values. This early understanding can save both parties from investing in a relationship that might not align with their core principles, ultimately preventing heartache down the road.

A couple look at their smart phones while having lunch together. (Photo: Getty Images)
A couple look at their smart phones while having lunch together. (Photo: Getty Images)

Timing and approach

Of course, when and how you approach these tricky subjects is important. Approach these topics once a comfortable rapport is established. Prematurely delving into deep discussions can feel intrusive. Let the conversation flow naturally, giving you both a chance to gauge each other’s comfort levels. Pay attention to your date’s words, tone and body language, and show genuine interest in their perspective.

Instead of debating abstract concepts, share personal stories related to the taboo topic, for example, “I grew up seeing my mum being passed over for promotions in favour of her male colleagues so it made me determined to challenge gender bias when I entered the workforce.”

Personal narratives humanise discussions, making them more relatable and less confrontational. Sharing your experiences can help your date understand your perspective better and may encourage them to reciprocate.

By encouraging open dialogue and embracing the diversity of human experiences, we pave the way for genuine connections and relationships built on trust, understanding, and acceptance.

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