Matchmaker, matchmaker, make me a match … Find me a find, catch me a catch…
If the lyrics from Fiddler on the Roof were to be re-written in 2025, we’d hazard a guess the next line would be: “And please make sure they’re actually compatible for reasons beyond ‘you’re both single!’” Because let’s be honest, there’s a fine line between playing cupid and completely missing the (love) mark.
Whether it’s your best friend who “just needs to meet someone nice” or that perpetually single co-worker you swear would definitely hit it off with your cousin, amateur matchmaking can be as thrilling as it is risky. One wrong move and suddenly, brunches get awkward, group chats go quiet, and your reputation as “the one with good instincts” takes a nosedive.
So, how do you play matchmaker without becoming the villain of someone’s next dating horror story? We turned to LJ Hawkins, founder of the Sydney-based Unwritten Dating Club (which is currently giving singles a shot at love before Christmas with their eight-week matchmaking challenge), for a few ground rules that even Cupid could learn from.
“The golden rule … Don’t project your idea of love onto someone else,” LJ says. “Just because two people look great ‘on paper’ doesn’t mean they’ll actually click in real life. Chemistry is unpredictable and that’s the magic of it. If you’re introducing friends, do it with an open heart but zero expectations. You’re creating an opportunity, not forcing a result.”
In other words, your “he’s tall and she likes tall guys” logic might not cut it. Real-life chemistry isn’t something you can spreadsheet. And while your intentions may be good, matchmaking isn’t about curating your dream couple. It’s about reading the room (and the romantic readiness) of your friends.
“Step in when both people are genuinely open to meeting someone,” LJ explains. “Not when one’s heart is still stuck on their ex or the other just wants a rebound. Timing is everything. If you sense even a bit of hesitation, it’s probably not the moment. The best setups happen when both are in a curious, lighthearted headspace.”
Translation: don’t ambush your friend at a dinner party with a surprise setup while they’re still mid-breakdown over their last situationship.
Of course, even the most well-timed setups can crumble under the weight of overenthusiasm. “Absolutely,” says LJ. “The biggest [mistake] is overhyping it. Saying things like ‘you two are perfect for each other’ just piles on pressure and kills the vibe before they even meet. Keep it chill, low-stakes. Let it be a casual introduction, not a ‘potential love of your life’ announcement.”
That means skipping the pre-date PowerPoint or the unsolicited pep talk. Think of yourself less as a casting director and more as an easygoing emcee. You’re simply creating a space where sparks might fly. If they don’t, no harm done. If they do, congrats, you’ve earned bragging rights. (And possibly a front-row seat at a future wedding.)
“Honesty starts with you,” LJ adds. “If you’re casual and real about it, they will be too. Instead of ‘give it a chance, you never know,’ say something like, ‘just go have fun. Worst case, you meet someone new.’ It removes the awkwardness and gives them permission to just be themselves.”
And, if you’re feeling tempted to script their first date like a rom-com, LJ’s festive-season advice is refreshingly grounding. “Keep it light and playful. Don’t script the story, just open the door. The best love stories unfold when no one’s trying too hard to make them happen.”
It’s a philosophy that also underpins her approach to professional matchmaking. Through Unwritten, LJ has modernised what was once a closed-off, high-cost industry, transforming it into something far more relatable. And affordable.
“Unwritten’s matchmaking is unique because it’s not just about throwing people into an event or relying on algorithms, it’s a full experience,” she explains. “I act as your personal wingwoman, use AI and my intuition to help make matches, and encourage all my clients to attend events so they can meet singles in real life. Plus, every client gets a spotlight on my ‘Inside the Matchbook’ social series, which introduces them to a wider audience of singles who might be watching from the sidelines.”
It’s this blend of “map and magic,” as she puts it, that sets Unwritten apart. “The data helps me see potential compatibility, but intuition is what turns that potential into something real,” she says. “Seeing someone in a social setting gives me insights that no algorithm can capture.”
And while LJ’s eight-week challenge might promise participants at least three dates (and the possibility of up to sixteen!), her goal isn’t just to spark romance — it’s to get people reconnecting with themselves. “People often date from a place of fear or pressure – trying to find someone instead of becoming someone who’s ready for love,” she says. “Our challenge slows that down. It helps singles date intentionally, understand their patterns, and show up as their best selves – not their most anxious ones.”
So, whether you’re setting up two mates over margaritas or secretly planning your own romantic “eight-week challenge,” remember: matchmaking is less about control and more about curiosity.
Or, as LJ puts it, “Courage looks like saying, ‘I’m ready to try something different.’ The dating world can be brutal, but once you let go of needing control over how or when love happens, things start flowing. Be open to surprises. That’s where the magic usually hides.”
Because if there’s one thing the holidays (and LJ Hawkins) remind us, it’s this — love can’t be forced, but it can definitely be introduced.