Want To Play Matchmaker? Here’s How To Create The Perfect Group Date

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Want To Play Matchmaker? Here’s How To Create The Perfect Group Date

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You know two people who would be perfect for each other but they refuse to be set up. This is what you need to do

airing two people – not the same as dumping a bunch of singles together – requires a different strategy. It needs to be done subtly, elegantly, preferably on the sly – especially if you know they will make a good fit but won’t agree to a one-to-one. Cindy Leong, dating and relationship coach at Divine Connect and Dolly Chua, chief matchmaker at Gaigai, tell us how to create that spark in a group setting.

1. It must be at your home

Because fancy restaurants add too much pressure. “For one, they’ll worry about their dining etiquette, which distracts from getting to know one another,” says Cindy. “A house party is great because you can control all the variables – whether to break out the wine, pull out a board game, or put on some music – all that’s up to you.”
2. Cap it at eight people

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More than that, and the pair you’re trying to couple up might not be able to interact as much, says Cindy. Don’t tell the other guests about your matchmaking plans. They might try to help, which will only make things awkward. Also, make sure your other guests aren’t all couples, so the pair won’t feel unnecessary pressure.
3. Seat them opposite each other
Once you’ve got the perfect conditions to put your guests at ease, ensure that the two you’re trying to pair up are sitting directly across from one another, and at the end of the table. It’s easier for them to converse than if they were side by side, and they won’t be distracted by too many people if they’re at one end, so there’s more opportunity to chat each other up.
4. Don’t invite the bros
“If you must invite friends in common, avoid his guy friends at all costs,” warns Dolly. When a man is with his “bros”, he will speak their language. And frat-boy locker room talk isn’t a great way to make a first impression. What’s worse, Dolly says, is that he’ll probably retreat into his comfort zone and engage less with the woman you’re setting him up with. Cindy adds that you should avoid inviting friends who know either of the pair, so that nobody ends up feeling awkward.


5. Drop the labels and don’t overshare

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Never imply that you’re setting them up on a “date”. Instead, say that the gathering is for everyone to hang out and have fun. Or that you want to try cooking a new dish and need some guinea pigs. For each of the two you’re trying to bring together, you can casually drop hints about the other in the lead-up to the party, but keep to neutral areas like jobs, positive personality traits and common interests. You don’t want to do a hard sell and give the game away.


6. Have a before and after plan

Some people need a warm-up. Try setting the tone with a pre-dinner activity like an escape room (where you solve puzzles to get out of a room you’re locked in), before heading back to yours for the main meal. If things go well, suggest postmeal activities, says Dolly. “Bring up a bar you’d like to check out and let the night’s plans move forward naturally.” If the pair you’re trying to set up like each other enough, they’ll take it from there.


7. Prep your place

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  • Curate a playlist that lifts the mood and fills any lulls in the conversation

Let it run in the background. Mix in some chart-toppers for guests to sing along to. No heavy metal.

  • Stick to finger food

Leave plates of it here and there around your home (the coffee tables and kitchen counter are good spots) to encourage your guests to circulate – ideal, since you’re trying to discreetly create space for your two friends.

  • Set the stage by dimming the lights

Go for yellow lights, or try candles. People tend to relax and let their guard down when their surroundings are dimly lit. Perfect for two strangers to break the ice.

  • You need conversation starters

Especially when not all your guests know each other. Strategically placed statement pieces or travel snaps always help, or leave some board games and poker cards on the coffee table. Good icebreakers: Travel, hobbies, food. Stuff to avoid: Politics, religion, exes, sex.




This article is featured in HerWorld. Written by Davelle Lee on 20 October 2017

Cindy Leong
Cindy Leong
Cindy Leong is a sought after bilingual (English and Mandarin) Enneagram Personality Coach and Corporate Trainer in Asia, who can help you make sense of your professional and personal relationships. She is a member of International Coach Federation (ICF) and Singapore Psychological Society (SPS). Besides a Bachelor Degree in Psychology (majoring in Communications), she also has a Diploma in Business and has done in-depth research and studies in the areas of Organisational Behaviour and Gender Communications, both in Singapore and Taiwan. Through her expertise in corporate executive coaching, personal development, and relationship coaching, she has helped many professionals in their walk through challenging times, particularly in the areas of identity searching, relationship building and career breakthrough. Aside from being a published author of 2 books, she has also been invited by several radio stations and magazines as an expert guest speaker to provide insights into Enneagram, workplace conflicts and relationships.
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