Wingman 101

Just when I thought I was out, they pull me back in.

Now, dear reader, you may recall that I wrote a two-parter on dating apps in conjunction with Valentine’s Day 2016 (here and here), thanks to my colleagues (who aren’t single) conveniently taichi-ing the feature to me. (Side note: still single. So… spoiler alert.) Recently, Lunch Actually had a matchmaking masterclass for the media, and guess who the team decided to send?

Three guesses. First two don’t count.

In case the name sounds familiar, that because it is – Lunch Actually has a mobile app, LunchClick, a free, barebones mobile app of what it offers – and one of the apps I wrote in my feature. Lunch Actually is the brainchild of Violet Lim, and is a matchmaking/dating agency gathering profiles of individuals and pairing singles that the agency thinks would be a great fit.

Meet violet-wearing Violet, the head honcho of Lunch Actually.

Essentially, Lunch Actually is the matchmaking aunties of ye olde days, backed with data, and with a far greater reach. Or, to match the parlance of the current generation, your data-backed wingman/wingwoman.

Oh, just to clarify, the class was to help people matchmake friends, not be be matchmade – much to the chagrin of my friends.

Now, during the masterclass, Violet shared some common tips in matchmaking people – she calls them “7 Golden Rules”. Let’s get started, shall we?

So many potential wingmen and wingwomen…

1. Consent is Crucial
Before you even start introducing a potential date to friends or family members, get their consent first. Though your intentions are good, this sort of outside intervention can be perceived as being nosey and meddling around in the private affairs of others. Naturally, this also means no nasty surprises; don’t ask both of them out for a mutual outing, then conveniently disappear. Not cool.

2. Facilitate, not Fix
It is nigh-impossible to get an exact 100% match, and you will not get a 100% matchmaking success rate. So many external factors are at play – mutual chemistry, one may like the other but the other doesn’t reciprocate – that are beyond your control. Always remember your job is just to facilitate the meetup, and not to make sure the relationship sticks.

3. Observe and Perceive
Observation and perception is key to upping your matchmaking game. Take time to practise and hone your skills. Admittedly, this would be significantly easier for people with larger social circles than yours truly (more friends = more guinea pigs, I mean, potential to experiment). No blind pin-the-tail nonsense here.

4. Of Wants and Needs
Generally, singles have an idea of what they expect in their ideal partner. What you as a matchmaker are supposed to do is to find out what their expectations are, and filter them. Some criteria are non-negotiable to them (“needs”), while they are flexible for some (“wants”). Get to know why your friends/clients/targets have these preferences, and use your wisdom and discretion.

What are your non-negotiables?

Also, here’s where you need to disappoint your friends: odds are, you won’t be able to provide an exact 100% match. So here’s where the “needs” and “wants” come in. Start on the former, and if they have the latter, great; if not, you can still get started.

5. Tough Love
Adding on to the previous point, you may have some singles in your circle who have unreasonable or unrealistic expectations, and for these lot, some firm assertions need to be in order. If they are open to receive constructive feedback, let them know and understand that this is just as much the other person’s choice as it is theirs. Compatibility and compromise are crucial.

6. Time to Dig
There may be underlying reasons why someone is single, and it’s your job as matchmaker to find out. Be mindful, compassionate and considerate when you get people to open up, as these underlying reasons can get sensitive, ranging from past experiences and hurts, to low self esteem. Get to know their fears, and endeavour to help them get over their stumbling blocks.

7. First Impressions Count(?)
You know the saying about not judging a book by its cover? That applies here too – specifically, to you. Don’t write someone off as incompatible or ineligible so hastily.


There you have it. Seven rules to matchmaking, according to the CEO of Lunch Actually. If you have a large social circle with a lot of singles, this could very well be your calling. Alternatively, if all of this is way over your head, you could always point your friends to use Lunch Actually. Leave it to the professionals to un-single your friends.

As for me?

I’ll be hiding in my man cave, devoid of social interaction.

Yep, I’m now an Honorary Cupid.

Andrew Yew

Storyteller. Doodler. Gamer.

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