Rich,
Busy, and Clueless: The New Clients Fueling a $250,000 Matchmaking Boom
Technology has made the matching
process ever easier, which has had a mixed impact.
EXPERT OPINION BY HOWARD TULLMAN, GENERAL MANAGING PARTNER, G2T3V
AND CHICAGO HIGH TECH INVESTORS @TULLMAN
Jul 28, 2026
In the
decades before the scourge of the pandemic, admitting that you met your mate
through a marriage broker or an online dating service was generally regarded as
a confession of behavior somewhere between despair and desperation. It wasn’t
as bad as buying a mail order bride or marrying a pen pal who was in prison for
life, but it could still raise eyebrows. Blind dates, hooking up and one-night
stands were all deemed to be acceptable youthful behavior and not expected to
lead anywhere anyway. But marrying someone you met on Match.com just wasn’t
something you bragged about to your friends and neighbors. It smacked of having
no other choices and settling for someone equally at wit’s end.
However, Covid-19 gave
millions of cellar dwellers and wallflowers permission and the opportunity to
actively seek out companionship and even more substantial commitments in online
forums and dating services where they wouldn’t have otherwise been caught dead.
And to be clear, it was no longer confined to any particular age group or
gender. It wasn’t as pristine as Tom Hank’s and Meg Ryan’s romance in You’ve Got Mail, but at least it was no longer
perceived as pathetic. But the whole matching process—finding your future on
your phone—was never really accepted and always regarded as déclassé.
Technology has made the
matching process ever easier and easier which has had a mixed impact. Initial
connections were much simpler to secure because there were millions of people
in the database, but at the opposite end of the martial spectrum, equal millions
of would-be romances and suggested introductions were immediately thwarted by
tech-enhanced critical scrutiny and rejections resulting from a quick scan of a
prospect’s online persona. There’s a persistent FOMO-like sense among online searchers
that a better bet and a more attractive match are just a swipe or two away. So,
they keep searching and coming up empty. After all is said and done, the bottom
line has never really changed. Many people still think looking for love online
is for losers. This persistent attitude and a consistent lack of results have
led to user fatigue, disappointment, and large-scale abandonment of the online
services. And it’s created a resurgent demand for face-to-face personal
matchmaking services.
As a result, and
notwithstanding all of the subtle and not so subtle opprobrium, the U.S.
matchmaking industry has rapidly expanded to meet that demand. It now numbers
over 2,000 “professional” firms of various sizes and of widely different skill
sets, experience levels, and even pricing models. This number is, of course,
substantially supplemented by “helpful” parents, friends and other family,
know-it-all neighbors and yentas, and plenty of intrusive experts at the
office.
But the real explosive
growth in the business—more than two-thirds of the newer firms—has come from
corporate chains expanding nationwide, much like the model of H&R Block.
These numerous and readily accessible players occupy (and have actually already
overcrowded) the lower segments of the marketplace. Their stated efforts to use
technology and now AI to professionalize and
standardize a very sloppy, unregulated, and chaotic industry have mainly
resulted in dramatic price increases for their basic standardized and turnkey
services. These price hikes combined with a Wild West environment without rules
or regulations regarding any player’s behavior, promises, representations or
performance guarantees have brought the expected onslaught of crooks, con men
and scam artists – all enabled by A.I. and the awareness that no civilian,
client or customer can ever tell what’s really inside of their black box. High
demand, high prices, an ignorant and gullible customer base, and no applicable
laws make for an environment ideally suited to cheats and criminals.
But technology has also
been inadvertently responsible for the expansion of a singular high-end segment
of the match-making business which has thrived in the new
environment—especially on both coasts and in D.C.—by offering previously
unimaginably high prices for their personalized and customized services. Their
specific targets—rarely overtly stated—are tech-created rich nerds looking for
love with huge gobs of cash, no time, no class, and no clue as to how to
proceed to find a partner.
And there are lots of
new mini-millionaires like these being created every day by AI IPOs and the
expiration of all manner of lockups and other trading restrictions, especially
around crypto deals. They literally have more money than they (or their parents)
have ever had in their lives and almost no ability to evaluate which of these
firms might make sense for them to employ in their quest.
So, in the time-honored
tradition of the very best tech promoters and marketers, these poor suckers
fall back on the stupidest rationale of all: How can it be bad if it costs so
much? Worse yet, there’s clearly a Veblen effect as well which dictates that
higher prices for luxury or scarce goods increase the demand rather than reduce
it. And finally, there’s clearly a FOMO effect which the high-end and
high-priced personal matchmakers make very clear and that is that their time
and resources are limited, the number of great men or women out there who are
looking is a finite number, and waiting will never get you anything worth
waiting for.
The bottom line: the
highest-end boutique players in this very narrow field are perfectly
comfortable charging rates between $50,000 and $250,000 for their services with
no strings and no guarantees attached. They serve executives, high-net-worth
individuals, and successful entrepreneurs. And they’re getting these kinds of
numbers and growing their revenue every year. It’s all legal for now, but I
guess the real question—like so many Trumpian actions these days—is should it
be legal?
