What Matchmakers Do When Their “Best” Clients Can’t Find Love

It’s one of the toughest puzzles a matchmaker can face: A client who seems to have everything going for them still can’t make a match stick. When that happens, it may be time to look more closely at the client’s expectations, dating patterns, and the matchmaking process itself.

The answer isn’t as easy to answer as you might think. Sure, it involves unrealistic expectations, bad dating habits, and even a client’s resistance to feedback. But clients also have a knack for getting in their own way — and matchmakers themselves can fall into this trap, too. 

To learn more, I sought out the advice of Julie Ferman, an LA-based matchmaker and dating coach, and Alexa Cassill, a matchmaker at Modern Love Club. They told me why even singles who look ideal on paper can struggle to find love, and how matchmakers determine when it’s time to adjust strategy, or the client’s expectations.

Clients That Are Great on Paper Aren’t Always a “Great Catch”

A client could have the most impressive resume in the world, but if they aren’t self-aware, open to feedback, or willing to grow, then they probably aren’t ready for a successful matchmaking process.

I know, I know; Is there a more aggravating sentence than “Pretty people have problems too?” According to Alexa, highly accomplished clients can have unexpected dating blind spots. 

“You might think that someone who has it all going for them might have the easiest time finding a great partner because they may be able to choose whoever they want to date,” she told us, [but] possibly their status has led them to be more picky.” 

The pickier a client is, the fewer eligible daters there are to work with. There’s nothing wrong with a client wanting the best for themselves, but they run into issues when they confuse high expectations with high standards.

“The biggest mistake we’ll make as women is when we are inclined to veto, dismiss, discard, or overlook a potentially wonderful man for reasons that are secondary – not key criteria,” Julie explained. 

There’s nothing wrong with a client wanting the best for themselves, but they run into issues when they confuse high expectations with high standards.

It’s an old lesson, but one that never seems to go obsolete: When you’re too picky or too superficial, you end up losing out in the long run. 

This lesson isn’t only relevant to clients, but to matchmakers, too. In fact, it’s a rookie mistake: Just because a client looks perfect on paper doesn’t mean they’re anyone’s idea of a perfect match. 

Alexa took this lesson a step further, telling us that “The traits that helped [clients] develop a great resume aren’t the same ones that equate to relational intelligence.” 

“The traits that helped [clients] develop a great resume aren’t the same ones that equate to relational intelligence.” -Alexa Cassill, matchmaker at Modern Love Club

A client might be successful at work, have a million dollars in the bank, and have lots of friends, but that doesn’t mean they possess even the most basic tools to make a healthy relationship work. 

The ability to be vulnerable, to listen and respond appropriately to a partner’s emotions, to understand and communicate your own needs; these are far more valuable characteristics for matchmakers to work with than an impressive resume or a beautiful face. 

The “Best” Clients Are Willing To Grow From Failure 

Julie described her best clients as those who are “growth-oriented by nature.” As a matchmaker, you can learn early on in the process whether your client is truly ready to do what it takes for a relationship — including learning from their own mistakes. 

Some matchmakers, like Julie, screen for a client’s willingness to learn, grow, and change during the intake process. But if a client can’t articulate what they want, or if their expectations don’t align with reality, she’ll encourage them to join her as a student in her Boot Camp program before she considers taking them on as a client. 

“Without that willingness/eagerness to learn, grow, and evolve, I don’t have much hope for them, sadly,” she told us. This is why “half of the work I do for and with my clients is coaching related.”

Some matchmakers screen for a client’s willingness to learn during the intake process.

After all, some of us need help understanding the role we play in our own singleness. Matchmakers can provide a much-needed outside perspective, and shine a light on the obstacles clients don’t want to, or can’t, acknowledge. 

This is why matchmakers often make the best dating coaches. When even your most high-quality clients can’t find love, it’s time for you to delve deeper into their behaviors. What’s happening beneath the surface that you wouldn’t initially see? 

“Coaching and guidance is a key component for me in my service model,” Julie told us. She not only screens for a client’s willingness to learn, but to see just how much coaching they might need throughout the matchmaking process.

It’s all about a client’s self awareness, and whether they can understand why they do what they do or say what they say on dates. 

Matchmakers have to help clients understand why they do what they do and say what they say on dates.

As Julie explained, modern matchmakers always have to be able to answer the “why” question. When a client asks, “Why don’t I feel compatible with this person?” or “Why did you match me with him instead of him,” you’d better have an answer. And as a coach, you’d better be able to clearly and constructively explain it.

After all, if a football coach changes the players on a losing team without ever examining the way the team plays, he’d be fired. The same goes for matchmakers who make unsuccessful matches without examining the “why” behind the failures. 

Sorry, Daters: Perfection Is Impossible 

It’s easy to get caught on what Julie calls “the dating treadmill,” or the endless trudge towards the “perfect partner.” Clients have to remember that they’re not perfect, and their “perfect partner” also isn’t going to be perfect. When you seek perfection in yourself and others, you’ll always end up exhausted and alone.

Even the most “desirable” clients can get “addicted to the process, always looking for perfection or the BBD (Bigger Better Deal),” Julie said. “And at the first sign of difficulty, they’ll cut bait and head back to the trough.” 

When these clients seek perfection, what they’re actually looking for is relief: from loneliness, or the unknown nature of singlehood, or from insecurity.

A matchmaker’s job is no longer to simply soothe this fear with a match, but to help the client address the underlying fears so they can date with more clarity, level-headedness, and with a more open mind. 

Even the most “desirable” clients can get “addicted to the process, always looking for perfection or the BBD (Bigger Better Deal).” -Julie Ferman, Matchmaker & Dating Coach

In other words? Instead of seeing singlehood as a failure, they have to start seeing it as an opportunity for growth. 

One of the most important lessons a matchmaker can teach their client is to embrace the  uncertainty of both singleness and dating.

This doesn’t mean walking into a date with blind trust, but with an open mind. Clients shouldn’t start a date by asking themselves, “How many boxes do they check off?”, but by asking themselves, “What will we connect over?”

“If a client can start to see first dates as an opportunity for discovery, and lead with curiosity about what they might connect over, that’s where the magic happens,” Alexa explained. 

Giving and Accepting Feedback With An Open Mind 

There’s an uncomfortable truth that every matchmaker must accept: Sometimes, you’re the problem. If a client consistently ends up alone, it could be because their matchmaker is not explaining their process or giving advice in a digestible, respectful, and actionable way.  

When and if you figure out what needs to change, Alexa recommends breaking advice down into “actionable items” rather than sweeping generalizations. Telling a client they’re too superficial isn’t productive; telling them to note three physical and three non-physical traits they like about a date is a more useful exercise. 

“As matchmakers, we need to be expert feedback sharers,” Julie said. “[We have to] say what’s important for our client to hear, but in a way that inspires them to develop the courage to modify their behavior and practices.”

Alexa recommends breaking advice down into “actionable items” rather than sweeping generalizations.

Good matchmakers give feedback; great matchmakers can both give and receive feedback, and learn from it.

As the matchmaker, it’s up to you to look at both your client and yourself with honest, unbiased eyes. What could you both be doing differently? Are there behavioral patterns on either side that could explain why a seemingly good match ended in failure?

If you can’t express feedback to a client — or accept it from a client — in a level-headed, actionable way, then how can you expect them to learn? A client should feel empowered to change their behavior after receiving feedback, not broken-down and discouraged. 

“[We have to] say what’s important for our client to hear, but in a way that inspires them to develop the courage to modify their behavior and practices.” -Julie Ferman

If there’s a single lesson to take away from this, it’s that even the most impressive and high-performing clients and matchmakers will fail if they can’t learn from their mistakes — or from each other.