Meeting Singles Isn’t That Hard After All

Everyone is searching for the perfect icebreaker — the one sentence that effortlessly opens a conversation. For many, attending social or dating events can feel nerve-racking, largely because of one simple fear: What do I say? I understand this completely. I’ve been to plenty of social gatherings where my mind went blank. But when you’re dating, silence only makes an already vulnerable situation more uncomfortable.

Many singles who attend our events notice that we don’t provide icebreaker cards or name tags — and that’s entirely intentional. Our goal is to create experiences that feel organic, as though you met someone serendipitously rather than through a structured exercise. We curate environments where everyone shares the same intention: a real connection. What happens next is up to you.

That said, much of the advice circulating online about starting conversations is, frankly, unhelpful. If someone asked me, “If you could book a last-minute trip anywhere, where would you go?” my honest answer would be I don’t know. Or “What’s your biggest pet peeve?” — I have many, and none come neatly packaged for small talk. So instead of recycled prompts, I’ll share what has genuinely worked for me. Use these ideas as a foundation and let conversations unfold naturally and please do not use Chat GPT— ever !

Start simply. Always introduce yourself, offer a handshake, make eye contact, and smile. One of the most natural questions — and one you’ll likely be asked — is: “What brought you here?” People enjoy sharing how they discovered the event. Often, they’ll mention a friend who met someone through us, which easily opens the door to more questions. And if you’re speaking with someone you find attractive and they ask how you heard about the event, feel free to be honest — perhaps a friend told you there would be interesting (or attractive) people there. Hopefully, they’ll pick up on the hint ; ) a flirty compliment goes a long way. Just beware, this question can lead you down a dangerous path, which is to bash other dating events or talk about horrible past dates. Please avoid any negative talk. It’s too much information for someone you just met and if it’s the only thing you have to talk about it’s a big red flag. 

I’m not opposed to asking what someone does for a living, as long as the conversation doesn’t stay stuck there. If someone is a family doctor, you might ask how recent changes in Quebec’s healthcare system salary structure are affecting their work. If they’re an engineer or accountant, you may discover a shared connection or curiosity about their career path. What someone does professionally often reveals a great deal about who they are — just use it as a bridge to broader topics.

Asking where someone is from and where they live now is another great entry point. People love talking about neighbourhoods and real estate. At one of our dinners, I asked a guest where they were from. When they said the West Island, I jokingly assumed they went to West Island College — and I was right. If they live in a lively area, you can compare favorite cafés, restaurants, or local activities. These conversations feel familiar and easy.

It also helps to stay informed. Scrolling through your X (Twitter), Bluesky, or news feed before an event keeps you aware of current events. We live in turbulent times, and having a general sense of what’s happening in the world allows conversations to flow more naturally and thoughtfully.

Once you’ve established rapport through lighter topics, don’t be afraid to go deeper. Lingering too long in small talk can be exhausting — it forces you to constantly search for answers. Deeper conversations, on the other hand, allow you to speak from a more authentic place.

At one of our events, I asked a guest about their background. They shared that they were Lebanese and Muslim, though not particularly religious. They explained which traditions they chose to observe, which they didn’t, and how they felt strongly that any future children should be free to decide their own relationship with religion. This naturally led to a broader discussion about values, relationships, and compatibility — far more meaningful than surface-level chatter.

The truth is, you shouldn’t be afraid to ask personal questions when dating. Very few topics are truly off-limits, as long as they’re approached with respect. If a question ever feels inappropriate, that’s your cue to set a boundary or step away. But thoughtful, serious conversations create space for genuine connection. If you’re not willing to be real, connection simply won’t happen.

Humor and lightness are essential — but balance is key. If everything remains playful and surface-level, it rarely leads to a match. Leave room for vulnerability, sincerity, and depth. That’s where chemistry lives.

I hope this helps you navigate your dinner party experience with confidence and ease.

Read on to the next post to discover what happens once you receive a match.