11 Secrets of Matchmakers

In an age of dating apps and casual hookups, matchmakers may seem like a relic from another era. But although they've been bringing people together since long before we were swiping right, matchmaking as a profession is still alive and well. We spoke to several matchmakers to get a glimpse at how their job really works, from their sixth sense for making matches to how they deal with picky clients.

1. THEY’RE ALWAYS ON THE CLOCK.

Whether they’re shopping for groceries, waiting in a doctor’s office, or traveling on vacation, matchmakers always have their eyes peeled for ideal partners for their clients. “Being a matchmaker is not a 9 to 5 job,” matchmaker and dating coach Bonnie Winston tells Mental Floss. “24 hours, seven days a week is more like it. My employees go home, but I never close!”

Winston, who often works on weekends and evenings, also gives her clients dating advice before, during, and after dates. “It is not unusual that clients call me with inquiries about what they should wear before certain dates,” she says. “Or, I’ll get calls in whispered hush tones—secretly from bathrooms in dining establishments—to ask me questions on etiquette, or if they can hook up with their date because they have great chemistry,” Winston says.

2. THEY HAVE A SIXTH SENSE.

Romance is mysterious—no one can predict whether two strangers will meet and fall in love. But successful matchmakers possess a high level of emotional intelligence and intuition that guides them in their work. Winston, who made her first successful match when she was 16 years old, says she just has a natural sense of which people would be good together. “Matchmaking isn’t something that can be bought or taught,” she says. “I will meet someone and just know when they are a good match for one of my clients.”

3. THEY’RE PART THERAPIST/LIFE COACH.

Matchmakers meet with clients, interview potential matches, dispense dating advice, and attend networking events. But some also perform background checks, administer personality testing, and build psychological profiles of their clients. The best combine a therapist’s listening skills and objective perspective with a life coach’s ability to motivate. Matchmakers may also interview their clients to determine why past relationships have failed, and help them formulate a strategy to achieve their relationship goals.

4. THEY’RE MASTERS AT NETWORKING.

The most successful matchmakers love people. Meeting people, listening and talking to them, and ultimately pairing them together excites and inspires them. In a Reddit AMA, three matchmakers at Three Day Rule explained that successful matchmakers are extroverts, and highly confident when approaching new people. “You really have to be able to walk up to anyone. We go up to people on the street all the time and say ‘Hey, are you single?’ so you have to be ok embarrassing yourself a bit,” they write.

Besides speaking with people they encounter in daily life, matchmakers may also rely on their networks of family and friends. “My mother is one of eight siblings and I have literally dozens of cousins who are well aware that there is a ‘yenta’ in the family. I tap into those resources, too!” Winston says.

5. THEY WISH PEOPLE WOULD BE WARY OF PHONY MATCHMAKERS.

Although some reputable organizations offer courses and certifications in matchmaking, matchmakers don’t need any formal training to do their job. “Some [of these organizations] are legit, but others are just about the revenue,” says Jamie Rose, the founder and CEO of Rose Matchmaking. Similarly, some matchmaking companies are more about maximizing profit than helping people find love. Scammers who start these matchmaking businesses take advantage of desperate, lonely people looking for love.

So how to tell which businesses are legitimate? Watch for these red flags: matchmakers who won’t meet you in person, companies that have recently changed their name (perhaps to evade detection or create distance from angry former clients), sites that don’t have testimonials (or where the testimonials seem fake), and companies that have many negative user reviews.

6. OVERLY PICKY PEOPLE FRUSTRATE THEM.

Matchmakers get frustrated when clients have unrealistic expectations about love. “There is no such thing as a perfect match, and some people come in thinking that there may be,” Rose explains. Clients may also have emotional blocks that get in the way of finding love. “Some people say they want to get married but they don’t really want to,” Winston says. “They turn down every potential date for a ridiculous amount of petty and inconsequential reasons.”

Jennifer Hayes, the Director of Operations for South Carolina Matchmakers, adds that because bad relationships tend to harden people, matchmakers must encourage clients to keep their hearts and minds open to love. “One of the biggest hurdles we have as a matchmakers is encouraging clients to stay open to the possibilities of finding love,” she tells Mental Floss.

7. SOMETIMES THEY HAVE TO BE BLUNT.

When a date goes poorly, matchmakers must walk a fine line between being honest and being tactful. “My least favorite part would be telling one client that another client wasn’t interested in them,” Rose says. Although most people don’t enjoy getting rejected and hearing about their off-putting habits, it’s essential that matchmakers be blunt with their clients. By speaking the truth in a kind yet firm way, matchmakers can build a trusting, productive relationship with their clients.

8. DATING APPS CAN MAKE THEIR JOB HARDER …

Dating apps give people a huge number of potential matches at their fingertips, but most apps don't vet matches—and good results are not guaranteed. “[Dating apps] make things so impersonal,” Winston says. “[Users] are deleting really good people forever so easily in seconds with their fingertips. And scratching their heads [about] why they can’t meet anyone.”

In addition, many dating apps are free, while matchmakers charge for their services. Matchmakers say that free apps propagate the view that finding love shouldn't cost anything, and thus threaten matchmakers’ livelihood.

9. … BUT APPS CAN ALSO DRIVE CLIENTS TO THEM.

While apps may be many people’s initial foray into the dating world, a disappointing experience can lead unsuccessful daters to a matchmaker. “Honestly I think [dating apps] impact [our industry] positively,” Rose says. “People who try those apps or sites see that they are about quantity not quality, and then they research better options and find me.” Winston adds that matchmakers slow down the online dating process. “People who come to me are sick of swiping, scrolling, sexting and texting, getting poked, and being ghosted. They are burnt out,” she says. “I bring back old-fashioned courtship and romance.”

Matchmakers also lend a human element that’s often lacking in online dating. "We know as matchmakers that setting people up requires knowing them to some extent, and knowing people requires time. Unlike online apps we get to know our clients and build relationships with them so we can effectively match them," Hayes says.

10. THEY MAKE CLIENTS LOOK THEIR BEST.

Visuals and first impressions play a huge role in dating, and good matchmakers help their clients improve their image. “You’d be surprised how many people come to me with terrible selfies to find love!” Winston exclaims. Because she owned a fashion photography agency, Winston stays connected to top photographers and hair and make-up artists, and she provides her clients with professional photo shoots. “I want my clients look their best while showing their authentic selves,” she says.

11. THEY LOVE HELPING PEOPLE FIND TRUE LOVE.

When matchmakers succeed in bringing two people together, they’re ecstatic. “I am joyful when my clients find joy in love. Especially when they immediately 'click'—I feel like I hit it out of the ballpark ... a homerun!” Winston says.

Rose adds that she enjoys changing people’s minds about each other. “I like when two people originally say no to one another, but you remind them of why they came to you. When that match works out you feel really good about it."