Can introverts survive dating events? I tried two to find out

I've never been particularly good at putting myself out there.

As someone who dislikes dating apps, I often find myself stuck in a frustrating situation. I would rather get to know someone naturally before deciding if I'm interested, but meeting new people requires actually talking to strangers. Left to my own devices, I'll usually find the one person I know and cling to them like a life raft for the rest of the evening.

Still, I knew that if I wanted to meet new people, I had to step outside my comfort zone. So when matchmaking events started popping up across Singapore, I became curious. Could they actually help create meaningful connections, or would they simply leave me mentally exhausted and counting down the minutes until I could go home?

To find out, I attended two dating events over the course of two weeks: Never Strangers and We Are The Socials.

Never Strangers

When small talk becomes a sport

Before attending, participants complete a personality questionnaire designed to help the platform find compatible matches.

Walking into Avenue Lounge felt a bit like the first day of school. Which is ironic considering it was being held in a club of all places.

The evening was packed with activities designed to get people talking. Unfortunately for someone who prefers to warm up slowly, many of them involved approaching complete strangers and making conversation on demand. It was essentially my social nightmare packaged as a game.

When the algorithm misses

After the activities came the matches.

My first match was 26, though I only discovered that after he casually mentioned he had just graduated from university. Meanwhile, I have been in the workforce long enough to develop lower back pain.

We were both perfectly pleasant and bonded over the answers we had matched on in the questionnaire. Once we'd exhausted the questionnaire answers, we mostly just sat there smiling awkwardly at each other, both seemingly out of ideas.

The second match was also significantly younger, which made me wonder how much weight the matching process actually placed on age and life stage compatibility.
The third match never showed up.

Ironically, the highlight of the evening wasn't one of my assigned matches at all. It was the women I met in between activities. By the end of the night, I had exchanged more Instagram handles with new female friends than potential romantic interests.

After the event ended, some of us stayed on at the club. A friend eventually decided to play wingwoman and introduced me to a guy I had been quietly admiring from afar. We ended up having a surprisingly good conversation. Unfortunately, he was only visiting Singapore on holiday. The universe clearly enjoys a laugh.

My takeaway

Never Strangers gets points for trying to create genuine connections, even if the matching algorithm still has a few kinks to work out. While I may not have found romance, I did leave with a few new friends and a slightly expanded social circle.

Next up was We Are The Socials, a dating mixer that promised a very different approach to matchmaking.

We Are The Socials

A different kind of dating mixer

We Are The Socials promises attendees two potential matches in one night: one based on data through AI and another based on energy through a Tarot pairing.

Compared to Never Strangers, the atmosphere felt noticeably more relaxed. The crowd was smaller, conversations felt more natural and the activities helped ease people into interacting with one another.

Perhaps that was because the event was held at Oche, a darts bar in Clarke Quay. It was an unexpected setting for a matchmaking event, but somehow made the evening feel less intimidating.

One thing I noticed almost immediately was the difference in effort. At Never Strangers, many of the men had clearly dressed for the occasion. At We Are The Socials, some attendees appeared considerably more casual, while the women largely looked as though they had put genuine thought into their outfits.

The moment of truth

Then came the matches.

My AI match was a 49 year old man who, let's just say, had long since stopped budgeting for haircuts.

To be fair, he looked about as thrilled to be matched with me as I was to be matched with him.
After a brief exchange, he walked away entirely and only returned after one of the organisers encouraged him to continue the conversation. Later, the organisers explained that they intentionally welcome quieter and more socially awkward attendees in the hope of helping them build confidence and meet people.

While I understand the intention, it did leave me wondering where the balance lies. If one person is completely unwilling to engage, the burden of carrying the conversation often falls on the other person.

Thankfully, my Tarot match was much better.

Unlike my first match, he actually asked questions. The more we talked, the more comfortable I felt opening up. We even discovered we had attended the same university. Was he my soulmate? No. But he was a reminder that good conversation can make even an awkward situation feel easy.

Halfway through the evening, I noticed the women had naturally started gravitating towards one another, swapping stories and comparing experiences. For an event designed to create romantic connections, some of the easiest conversations seemed to happen when nobody was actively trying to impress a potential match.

So, how did it fare?

If Never Strangers felt like being thrown into the deep end of a social swimming pool, We Are The Socials at least handed me a float first.

The smaller crowd and activity-led format made conversations feel more natural, but the matching process still felt hit and miss. While the organisers clearly have good intentions, a little more vetting around compatibility, expectations and willingness to engage could go a long way.

So, are dating events worth it?

After attending both events, I am still not entirely convinced that dating events are the best route for introverts looking for love.

They probably work far better for people who are naturally outgoing, enjoy meeting new people and are comfortable striking up conversations with complete strangers at a moment’s notice.

Going with a friend definitely helped. Had I attended alone, there is a very real possibility I would have become the person contributing only ten words to an entire conversation.

These events require a certain level of confidence and social stamina, both of which I discovered are finite resources. By the end of the two events, I was completely drained.

That said, both organisers genuinely seemed invested in helping people make meaningful connections, and the intention behind these events is undoubtedly a good one. There are still a few kinks to work out, particularly when it comes to the matching process, but the foundations are there.

As for me, I am still holding out hope for a meet cute in a bookstore, café or supermarket aisle. Anything that does not involve being told to walk up to strangers and introduce myself.

Because if there is one thing these events confirmed, it is that finding love is hard. Finding love as an introvert is an entirely different challenge altogether. After attending both events, I realised the biggest obstacle wasn’t the algorithms, the Tarot cards or even the other attendees. It was getting myself through the door in the first place.

Ironically, the people I connected with most weren’t the ones I was matched with. One was a traveller my friend introduced me to after Never Strangers. Another was a man I met at the bar during We Are The Socials who wasn’t even attending the event.

Perhaps that’s because the best matchmaking service wasn’t the dating events at all. It was my friends, who repeatedly forced me to stop lurking in corners and actually speak to people. Between the two events, they introduced me to more viable prospects than the algorithms did.

Would I do it again? Probably not.

But am I glad I did it? Surprisingly, yes.

After two dating events, one AI match, one Tarot match and enough small talk to drain my social battery for a month, I learnt two things. Firstly, chemistry cannot be engineered. Secondly, my friends are significantly better matchmakers than the professionals.