Reading · Modern Dating Advice For Men & Women

Matchmaking is one of the oldest professions out there, yet there are many misconceptions around the service, who it benefits, and how it works. I have been hired by several matchmakers locally and across the country on behalf of their clients over the years to take photos.

In most cases, I turn down requests as I prefer to work with clients directly over difference in approach, strategy (I don’t photoshop images and I don’t take stiff portraits for dating purposes) but also because I don’t want to (in)directly endorse specific matchmakers.

I was interviewed by the New York Times a while back for an article about matchmaking, and although most of the conversation didn’t make the article, I will touch upon some of the important points below.

Typically, a client hires a matchmaker to provide dates for him (or her). Matchmakers often provide the client with 3 or so deal-breakers to choose from and the matchmaker uses their network to find dates.

Professional matchmakers often require signed contracts, up front payment and are really good, charming salespeople. Look at their photos, there is a reason why they hire attractive people to scout clients, find dates and close deals.

There is often no guarantee for success i.e. relationship or marriage, and once the contract is fullilled i.e. 3 dates, the client has to pay for more services (per date) or hire the matchmaker on retainer i.e. ongoing monthly fee or the like.

Most matchmakers do not have a reputable business listing i.e. Yelp or Google. Some have actually deleted profiles, changed business names in order to hide reviews.

Similarly, most clients do not want to admit to hiring matchmakers (embarrassment or being viewed as desperate). On occasion, a matchmaker may have a decent amount of reviews but if you dig deeper, they may be biased i.e. come from friends, family, spouses, or third party providers i.e. stylists, employees, photographers or the like.

Given lack of transparency, it can be hard to find reliable info. On top of all that, reviews from trusted sources can also be biased given different intentions, filters i.e. reviews from men vs women, different deal-breakers, different age ranges etc.

Most matchmakers have more experience and relatively higher success with men as men have higher incomes and in modern society are viewed as pursuers while women are viewed as being pursued. Things are changing, women are outpacing men in terms of degrees, they are earning higher wages and are taking a more proactive approach in their love lives.

The other driving change is time. A lot of people took a break from dating during the pandemic (intentionally or indirectly) i.e. safety, isolation, WFH, friends moved aways, lay-offs, rising costs, things closing down and more. For those seeking families via natural births, timing is a concern and many are making up for lost time. More and more women are freezing their eggs and more and more companies are offering such services with their compensation packages.

During COVID, a number of women used dating apps, many against their own desires. I typically worked with men pre-covid but since 2020, most of my clients are now women. Many swore off dating apps prior but felt they had little choice with dating if they wanted to meet someone sooner than later.

Around 2023-2024 as we came out of the pandemic, people started to abandon dating apps as they raised rates, reduced free services and made the experience worse for all. As such, many women started to seek out alternative ways of meeting men including singles events, speed dating, date-me-docs, run clubs, and of course matchmaking services.

Matchmaking services can be very hit or miss but there are several high-end matchmaking services that only work with men. The reason for this is that they view the dating pool for UHNW (ultra high net worth) women relatively small (on average). It’s not that there is no shortage of men willing to date wealthy women, nor that women don’t have the money to spend on such services but rather these women often seek men who are equals i.e. wealth, age, education.

On average, men who would be in this dating pool often seek women who are younger, may not care about wealth and in many cases avoid women who have careers especially law, tech, banking, executives etc. Unfortunately, many men seek a woman who they can boss around, and even manipulate (easier to do if they don’t have their own money, don’t have friends etc). They don’t want a woman who will threaten their manlihood, talk back to them or challenge them intellectually.

Matchmaking services have repeatedly told me that their female clients are much harder to help out given preferences, and urgency. It also doesn’t help that there is a good-man shortage in the dating pool.

Of course there are matchmakers who do take on women but I would carefully tread those waters as clients often overlook details in contracts. For example, say a woman provides 3 deal-breakers to a matchmaker (which is typical) - wants a man 35-42, have a good job (not rich but doesn’t need money) and wants kids. This all seems resasonable and there are definitely lots of men in this boat but the caveats are what often get clients i.e. the man has kids already, lives far away, is of a different ethnicity, religion or politics. These items are often perfectly normal deal-breakers that people should demand but often are forgotten when dealing with a matchmaker (especially for the first time).

For men hiring matchmakers, the task can be easier as men have fewer requirements i.e. indifferent about religion, ethnicity, wants a certain age (usually younger), doesn’t have kids already and is attractive. I am not saying this is every guy or most guys but the story is common enough that is sounds familiar. Fewer deal-breakers is easier to work with (even if they are unrealistic).

Matchmakers can definitely work for women, but there are so many variables involved that it is impossible to know if it will work for you based on your urgency, budget, preferences/deal-breakers, who you hire and more. There are lots of men who would gladly date an equal but would they consider working with a matchmaker themselves? That’s another question.

It’s not uncommon for matchmakers to seek out dates on dating apps or even set up dates with friends just to meet their quotas specified in contracts. Some matchmakers go on Linkedin to find men and in many cases, they are married.

It’s important to do your own due diligence when spending money on a matchmaker. Google reviews are often inflated (more so than Yelp). Look up reviews on BBB. Get someone to review contracts. Ask dates how they know the matchmaker.

Dating is a process and that process can take a long time so it’s important to be patient. Be ready for matchmakers who will push you strongly to manage, adjust and even lower expectations.

There is a saying in the matchmaking industry that goes something like this: I am a matchmaker, not a magician.

Dating is not hopeless, but you shouldn’t rely on matchmakers only or think finding love will be quick. These things take time and require you to be proactive (get out of your comfort zone), try alternative outlets for meeting men and learning how to cut off time wasters sooner (they will take a toll on your mental health and make it harder for the next guy to make a good first impression).

Do a google search on matchmakers i.e. ‘matchmaker reddit reviews’ or ‘matchmaker lawsuit’

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