The Scoop: The dating world can be a scary and lonely place. And as dating app fatigue grips modern singles seeking true connections, they are increasingly turning to traditional matchmakers for a helping hand. We talked to Siobhan Copland of Cupid in the City to learn what distinguishes successful matchmakers in the field and why singles should consider choosing a professional matchmaker over an app.

Newer doesn’t always mean better — especially when it comes to methods of finding love. Siobhan Copland, founder and matchmaker at Cupid in the City, said she wishes she could shout it from the rooftops. 

“People are realizing that living life online all the time is not good for any of us, and that

sometimes going back to the old-school way of doing things is actually the best way,” she tells us. 

Screenshot of Cupid in the City logo and website home screen
Siobhan Copland dove into her matchmaking expertise to give us tips about finding our own love experts.

With years of experience and a passion for connecting singles, Siobhan’s work focuses on using a deep-rooted and authentic understanding of client needs to offer a personalized touch to the often-frustrating but oh-so-rewarding love-seeking journey. Cupid in the City (London being the “City”) was created based on these heart-led strategies, and hones in on serving the metropolitan’s educated and professional population.

As a successful matchmaker herself, Siobhan believes strongly in the value of experience and intuition over formal training, and has built a reputation on using her human-centric skills to facilitate meaningful and lasting connections for hundreds of clients. 

If you’re considering adding a love expert to your search platoon, Siobhan offers a handful of insights on how to find your perfect, well, match  — as well as tips for maximizing your efforts once the official trek begins. 

What Makes A Good Matchmaker?  

The person you choose to spend your life with is arguably the most important decision you’ll ever make. That said, you don’t want just anyone by your side helping you make this happen — you want the best of the best (within budget, of course).

First thing’s first, Siobhan tells us, experience in the matchmaking game isn’t enough to make someone worth their price. Conversely, you’re going to want to invest your precious time and well-earned money on someone who has earned their stripes. She explains:

“Reputable matchmakers charge for their experience and their network. Someone new to the game is unlikely to have much of a network, so you are taking a big risk that they may have no real understanding of what makes a good match, and may not have good match options for you.”

Instagram photo of young Black woman smiling and showing off her engagement ring with the words Is This Your Goal? at the bottom of the photo
Seek out an experienced matchmaker with a passion for helping people in your demographic.

This means that a truly skilled matchmaker is going to be able to show you the receipts. In other words, they’re going to have a handful of success stories in their back pocket, and will be able to explain exactly how they found each match and why.

Siobhan explains that another telltale sign of an industry expert is someone who understands the value of finding (and sticking to) a niche: 

“Reputable matchmakers know their crowd and tend to stick to this as they build their network. For example, my demographic is pretty much Londoners who are professional, educated people, typically in their 30s and 40s. Now, if a 70-year-old woman or man comes to me, straight away I am going to refer them to another agency.”

Turns out, in this case, a jack-of-all-trades is not better than a master of one. Quality over quantity, always. 

Lastly, the key to teaming up with the matchmaker that is going to best serve you in your search for love is to approach the process exactly as you would in romantic dating. As you and your potential matchmaker (not a sales representative) are getting acquainted, you should be asking yourself: How well have they helped me open up to them? How well have they really gotten to know me? Are they just ticking off boxes or do they really understand my wants and needs?

“A matchmaker should be someone who cannot just introduce you to matches but also really guide and support you while dating them, so you must have that rapport.”

Plus, Siobhan points out, to get through the ups and downs of the love-finding process that will surely ensue, you and your matchmaker need to actually like each other:

“A matchmaker should be someone who cannot just introduce you to matches but also really guide and support you while dating them, so you must have that rapport.”

Red Flags To Look Out For

Just like in dating, it can be equally as important to know what you don’t want in your matchmaker as what you do want. Luckily, Siobhan touches on a handful of red flags to look out for as you find your ideal love-seeking guide. 

Close up photo of two glasses of wine held by a young couple smiling at each other
You should always meet your love expert IRL or over Zoom to make sure they’re the real deal.

To start, you’ll need to pay close attention to the price a matchmaker is charging. If they’re new to the game but asking for just as much as the industry vets, this should be an immediate “no-go” for you. Again, the key is to have proof that they not only have the experience but the track record to back up the prices they’re charging. 

Next, Siobhan tells us, you should never hand over a single dime to anyone before you’ve gotten the chance to meet in person (or at least over Zoom).

“If they’ve never seen you in the flesh or online, they’re not giving you a fully personalised matchmaking service.” 

And, as any good lawyer would say, you should never agree to pay without a contract, and you should certainly not sign the contract without reading it. 

Siobhan also adds an interesting comment about bad reviews, and it may not be what you’d think:

“If you see any bad reviews, you should do some research there, but just know that they don’t always give the full picture, particularly if you’re dealing with a larger organization. The more customers someone has the more complaints they get — that’s how it is with any business.”

So, if throughout your search you encounter some negative customer feedback, don’t panic — or, at least not yet. Consider that these reviews could be badges of honor designated for true veterans, and continue your research with an open mind.

To Invest Or Not To Invest?

Hiring a matchmaker can feel like an extravagance compared to all of the other expenses that come with being an adult. And although Siobhan won’t tell you to stop paying your rent or car payments, she will insist that you start viewing your love-seeking journey from a new perspective:

“If you’ve tried the other avenues — particularly online dating —  and you have exhausted those options, it becomes a question of using your time wisely. For example, you may have been searching for love for years. But with a matchmaker, even if it takes you a year to find someone, it will still be less time than if you stuck with your original approach.” 

Photo of the silhouettes of a young man and woman as the man proposes
A matchmaker can lead you to love, but they can also lead you to individual growth.

Embarking on a matchmaking quest also offers a unique benefit for those riding the self-help train: a chance to level up your personal development game.

“You’re not just investing in finding a partner; you’re investing in yourself. A matchmaker can provide moral support, honest feedback, and insights that help you grow as an individual,” she adds with a smile. 

Ultimately, enlisting the help of a matchmaking expert with a personal touch is about so much more than finding a teammate to play tennis with. By using the support and guidance of someone who knows your dating goals inside and out, you can uncover new information about yourself, put your needs at the forefront, and create a partnership that complements your life in ways that an online dating app probably never could.

Because, as Siobhan points out: “Personal relationships shouldn’t be left to algorithms, but to people who have a heart for it.”