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Resident Advisor: Matchmaker Gillian McCallum

Still single? Here’s some expert dating advice from the CEO of one of the UK’s most prestigious matchmaking agencies that will see you coupled up in no time

7 September 2022

As summer’s heat dissipates into autumn, cuffing season is upon us. Not heard of cuffing season? It refers to the period of autumn and winter when single people are considered more likely to look for more settled relationships instead of short summer romances. The term was shortlisted by Collins Dictionary for its Word of the Year in 2017, FYI.

To help singles to make the most of this time, we picked the brain of dating guru Gillian McCallum, chief executive of matchmaking agency Drawing Down the Moon, to find out how dating has changed since the pandemic, her top first date advice and the benefits of handing it all over to a professional*.

Of the agency’s many eligible London-based clients, the majority live in Chelsea, so we asked Gillian for her insider list of the best first date spots in the neighbourhood too.

Are you ready for love?

 

HAS THE DATING LANDSCAPE CHANGED SINCE COVID?

Absolutely. People’s dating priorities have totally shifted. I think a lot of people realised what is important to them and the things that people really cared about pre-pandemic have become far less important. It’s stopped mattering so much if he is 10 inches taller than her, or if she’s not a 10/10 on the beauty scale.

When Covid first hit, all these high-achieving men and women with phenomenal careers and very busy lives were suddenly isolated. They might have had all these boxes ticked in their lives – career, home, friends, social life – but they didn’t have the thing that really counted: connection.

During that time, people’s personalities had to shine because of the restrictions on dating. People couldn’t go out to bars, events or restaurants, so without all the background noise, people could really focus on the other person and whether or not there was true compatibility. Dating became very much focused on personality, connectedness and like-mindedness.

 

WHICH OF THOSE ATTITUDES DO YOU THINK HAVE REMAINED?

People were very serious in their search during the height of the pandemic. And that seriousness in finding a partner is still there; people continue to be focused on finding someone wonderful for them. We can see that through our application levels, which continue to be high.

We haven’t forgotten what the lockdowns were like. There’s still that sense of, “I wouldn’t want to go through that again on my own.”

It’s very easy to be bowled over by someone who’s spectacularly good-looking that maybe isn’t the right person for you. Or be distracted by external stimuli. But I think people have learned that what really matters is “Is this a good person? A kind person?”

 

HOW WOULD YOU SUGGEST SINGLES MEET POTENTIAL ROMANTIC INTERESTS IN REAL LIFE?

Talk to people! Don’t bother with lines. You could quote Shakespeare but if that person decides that you’re not for them, it’s never going to work. It doesn’t really matter what you say, as long as it kick-starts the conversation. Try to find some commonality. Ask them about their drink or meal or accent. If there’s a possible hint of interest, you’ll get a positive response and then you can take the conversation anywhere.

Join organisations or societies that host talks, events or lectures on midweek evenings, with an opportunity for mixing afterwards. That’s where you’re going to find like-minded people who are potentially single. The Royal Geographical Society is great for that and close to Chelsea.

This goes for the 20-something singles, too. They have grown up with the internet and often don’t know how to start to chat with someone of the opposite sex other than through texting. Chatting someone up almost doesn’t even exist for them as a concept but it’s a lovely thing to do.

 

DO YOU CATER TO THE LGBT+ COMMUNITY?

We wholeheartedly support the LGBT community. Actually, Drawing Down the Moon was a pioneer in matchmaking LGBT singles through a separate company that was set up 30 years ago. Although it has since closed, when we do receive an enquiry from an LGBT single, we will do our best to matchmake them with the most suitable specialist matchmaker we can find because we feel that we would be doing them a disservice if we tried to do it all.

 

Don’t have such strict criteria of what you’re looking for; it prevents you from finding love.

 

HOW CAN SOMEONE MAKE THE MOST OF A FIRST DATE? 

First of all, remember that first dates are meant to be fun and engaging.

Make it a proper evening date somewhere nice. Pick a bar where you can hear your date; somewhere with a bit of an atmosphere, but not too loud, and make sure that they serve alcoholic and non-alcoholic drinks in case your date doesn’t drink.

The first time you meet, I recommend you don’t have a date longer than about 90 minutes. Leave it with something left unsaid and room to explore. Don’t go to a restaurant on your first date, they’re too formal and require too much time spent together. Don’t go to a café. Choose somewhere to sit like a cosy banquette so that you can sit next to your date – not opposite them. Some successful people can treat dates as some kind of interview but you’re not interviewing for the position of spouse. You’re just trying to work out if you’d like to go for another drink together.

There’re huge numbers of people competing in the dating scene; it’s competitive. So make an effort. If you’re a woman, do get dressed up; wear something you enjoy wearing and try to look your best. But try not to be disappointed if your date doesn’t. Just be gracious about it. A lot of guys are clueless [about clothes], especially about what they should wear for a date.

Gentlemen, try to remember to ask questions. Men are notoriously bad at asking questions on a date. If your date is guilty of this, know that you’re not alone. It usually means that they want to impress you and show you who they are.

If you really want someone to fall in love with you, do something scary together like an amusement park ride. Something that gets the heart rate up. The physiological sensations of fear and falling in love are actually quite similar.

Gents, never suggest splitting the bill. Don’t do that. People hate me saying this but men should pay on the first date. I’m sorry guys, but you know that you should.

 

WHAT ARE YOUR FAVOURITE FIRST DATE SPOTS IN CHELSEA?

The Ivy Chelsea Garden has an intimate, romantic dining setting surrounded by beautiful greenery and decor. Great for a second or subsequent date with candle-lit dinner and drinks, followed by a romantic walk down the King’s Road.

Granger & Co. on the vibrant Pavilion Road, has a wide range of drinks and sharing suggestions. It is beautifully lit and has a lovely ambience and a secret outdoor dining spot outside, creating a warming atmosphere for a first-date setting.

With a cosy and inviting environment, The Chelsea Cellar is a wonderful date location. Who doesn’t love a food and wine pairing, combined with great company in an intimate and private setting where it’s not too loud?

The place to be for a really fun date, Chelsea Funhouse is perfect for those who enjoy a game or two, with a lively and entertaining atmosphere. It’s great if you’re looking for a bit of fun and activity for the first date. The decor is also one to remember, and is a great conversation starter!

As well as a stylish upstairs restaurant and bar, Bluebird has an outside area to rival other Chelsea bars and restaurants. The patio is a beautiful, alluring spot at any time of year as there’s always a buzz. It’s definitely worth heading there early to ensure you get the perfect spot outside for a cocktail served with impeccable service.

 

WHAT ARE YOUR ALL-TIME DATE FAILS?

Again, never suggest that you split the bill. Don’t air your dirty laundry on a first date, and don’t talk about your exes or your dating experiences.

Don’t ask someone why they’re single. It sounds like a compliment but people get defensive about it – as if you’re asking what’s wrong with them. But if you are asked this, say, “I have a really fulfilling life and I would only want a very special person to share it with me.”

 

WHAT’S THE BEST WAY TO FOLLOW UP ON A DATE?

No matter how the date went, always be kind and gracious.

If you’re a woman and you had a nice time, send a message letting them know that you got home safely, that you enjoyed the date and that you’d like to see them again.

Gents, if you would like to see her again, take the lead and tell her that you’d like to arrange to see her again, making sure to suggest an evening for your second date.

However, if the date was a 100% “no”, then send a clear and positive message thanking them for the evening. You could say, “I enjoyed our time together but, unfortunately, I don’t want to move forward. But I know that you will find the right person.”

Either way, be prepared that they might not feel the same way and try not to take it personally. There’s a whole cornucopia of reasons why someone might not want to go on a second date with you.

 

WHAT RED FLAGS SHOULD PEOPLE BE WARY OF?

This wouldn’t happen with one of our introductions because we make sure people are relationship-ready, but if someone tells you that they’re just looking for some fun, believe them. They are not going to change their mind because of how special you are or if you spend time together. It’s not happening.

 

AS A MATCHMAKER, WHAT ARE THE MOST COMMON MISTAKES SINGLES MAKE?

People often forget that it’s how someone makes you feel that’s the most important thing when you’re looking for someone.  They have such strict criteria of what they’re looking for – and it prevents them from finding love.

Chuck your lists in the bin and focus on values and how the person makes you feel. Whether you’re a man or a woman, every additional criterion you have for a match reduces the chances of you finding love. It makes the pool smaller.

So many people will end things early on because they’re worried about being wounded. Don’t do that. Don’t shoot yourself in the foot by telling someone you’re not interested just because you think they’re not interested in you. Wait until you hear something back. Quite often we find that men enthuse about a woman after a date but not necessarily during it.

In Japan, matchmaking agencies will insist that you go on two dates with someone no matter what you thought the first time. And I think that’s so important because some people just get so nervous that they’re not themselves. Or maybe they had a bad day. You just don’t know.

Let go of your expectations about how often someone should be texting you. That’s not an important requirement in love. Lots of people are really bad at texting for various reasons. It doesn’t mean they’re not thinking about you.

Give people a chance, no matter where you meet them. And if a friend has introduced you to someone who is deeply unsuitable, remember they’re a person who just wants to find love, too, so be kind. And don’t be mean to your friend, either; they were trying to help.

 

WHAT ARE YOUR THOUGHTS ON ONLINE DATING?

I’m very positive about online dating; I think it’s the way to do things. But that process of constantly swiping is mostly based on physical attributes and that can create a distorted perspective. A sense of disposability towards the people you’re seeing.

 

People often forget that it’s how someone makes you feel that’s the most important thing.

 

HOW DID COVID AFFECT YOUR BUSINESS? 

We had never been busier! It has been a very interesting few years. When the first lockdown was announced in March 2020, things were very quiet as we all adjusted. But then we saw application numbers go through the roof. We had to hire new matchmakers to help support all these new clients.

We wondered if we would see a drop in numbers when all the Covid restrictions ended and people were able to get back to bars and events but we haven’t, not so far.

 

WHAT DO YOU CONSIDER WHEN MAKING A MATCH? 

What we’re really hoping to achieve is long-term compatibility and it’s far more of an art than a science. We’re really looking at who the person is, what the person is looking for and what we think might also be good for them.

A part of our job is to spend time with and educate our clients, finding out what’s really important to them and encouraging them to let go of their long list of requirements. I get it, it’s nice to have a bit of a shared history, but how someone makes you feel is far more important than his or her career, schooling, hobbies or looks.

We consider where this person is in their life, and where they want to go in the future – and is this compatible with the potential match? Do we see enough differences in each person that they’re going to be interested in and entertained by each other, and potentially have a future together?

 

WHAT IS THE BENEFIT OF USING A MATCHMAKER?

In the same way that people outsource to experts in life, from personal trainers to hair stylists and accountants, we are the experts at finding love for people. We work incredibly hard at curating the introductions that we believe will have the best chance of a successful outcome, which is to find love. We estimate that there have been tens of thousands of children born as a result of our service, which has a 75% referral rate.

 

WHAT’S YOUR SUCCESS RATE LIKE?

It usually only takes around five introductions before they find love – often less. That’s already a much higher success rate for our clients coming to us after trying online dating or meeting people through work or friends. Often we get it right on the first introduction. That’s us setting the bar pretty high.

And there’s something magical about making a commitment to finding someone by joining Drawing Down the Moon that makes you really magnetic and even more likely to meet someone. So keep going to barbecues, events and dinner parties because there’s a really good chance that your person will suddenly appear.

 

HOW IMPORTANT ARE LOOKS TO MAKING A MATCH? 

Well, we don’t share photographs of our matches before they go on a date.

We used to share photos with clients in our office until a couple had a chance meeting, fell madly in love and were married even though they had both been shown one another’s photographs and neither of them had picked the other one.

 

WHAT IS THE BEST PART OF BEING A MATCHMAKER?

Changing people’s lives forever.

 

Membership to Drawing Down the Moon starts at £10,000. To apply, visit drawingdownthemoon.co.uk or call 020 7224 1001.

Resident Advisor

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