In order for Greenwald to tutor you as a matchmaker, however, you must pay, in full and up front, the "very pricey" fee for the intensive two-day workshop. If you need to cancel after paying, too bad: Your money will be diverted to Greenwald's pro bono karma fund, which she uses occasionally to help clients who cannot afford her daily rate.

The first day of Greenwald's training centers on public relations and pricing, while the second focuses on event management, tactics and communication skills. Both days last nine hours, during which none of the five students (maximum) leaves the room; lunch is delivered. But if a student lasts through training, she (and they are almost invariably female) will get customized career advice from Greenwald. "It's an incredibly flexible profession," she notes. "There's no degree requirement and no start-up costs as long as you own a laptop, and the hours and geography are whatever you want them to be. One boot-camp client wanted to work exactly from 9 a.m. to 3 p.m. in Chicago, so I developed a business plan for her in Europe to work in those hours."

Greenwald teaches her students to specialize in order to create their own matchmaking niches separate from those of the competition. Her last boot camp included a woman from Australia, a sixty-year-old retiree looking to tap into Boston's seniors market, and a Mormon widow. "When I wanted to break into the LDS community that I belong to, Rachel thought that was a great idea," says Chris Wilhoite. "It's a world where matchmaking isn't utilized as a profession."

Although the intensive training session focuses on building business skills, perhaps its most practical tool is Greenwald's own seal of approval. After class, she'll donate her rejected business requests to the matchmakers that she has nurtured. (Matchmakers can also purchase clients from each other if they think some are better suited for another customer.)

"Rachel's success is a huge thing," says Heidi Wicks. "She has an excess of clients she can't take in, and she passes them on to us based on our specialties."

Greenwald confirms this with a smile. "This is not a non-profit organization," she says. "It's a business."


The enormous diamond on Jaime Richards's immaculately manicured left hand is as distracting as it is comforting, but "it's nothing compared to the man who gave it to me," she says.

Although many of Greenwald's matchmaking graduates are single when they start their careers, a wedding ring can be reassuring when it's on the hand of the person you just paid thousands of dollars to help get you down the aisle. Reassuring enough that you're willing to listen to her blunt advice. "I hope I don't offend you, but I have to tell you," Richards says. "You should really never wear those tights with those shoes ever again. A man will look at you and get worried."

Of all Greenwald's local students, Richards is the closest in both style and ambition to her mentor, though the two differ on a handful of issues. "Rachel doesn't love that I don't go national, but I don't want to travel," Richards says. (One of Greenwald's wealthier clients, a billionaire from Texas, once flew her to him on a private jet. For such occasions, Greenwald exercises a buyout option, through which clients can pay more to purchase 100 percent of her time for an agreed-upon span.) "We were kind of at odds about that."

Richards discovered Greenwald's books after her seven-year-old daughter motivated her to become more aggressive about dating. "I was a single mom, and I had dated and been married enough to know I wasn't going to screw it up this time," Richards says. "I made a decision that I was going to research everything I possibly could about online dating, which was my only option at home with a kiddo."

She started experimenting with her mother, setting up an online dating profile for her and frequently logging into that account to reword aspects of that profile after her mother had changed them. It worked; her mother is now married. And Richards met her own husband, who runs a home-electronics business, through the same website. It was after that that Richards, who was working as a real-estate loan agent at the time, realized she could make a career out of matchmaking and took Greenwald's course last January.

Today Richards is a confident matchmaker and dating coach: If your hopes are not high enough, she will readjust them. If your expectations are too picky, she will correct them. If you are not assertive enough, she will flirt with people for you. Last year, temporarily blocked her home IP address after she winked at too many people for a client.

Her business comes with rules, and it comes with results. According to Greenwald, the single most common end to matchmaking careers is a lack of self-confidence. "People are typically terrified to charge what Rachel tells them to charge," Richards says. "But I'm completely okay with people walking away when I tell them the cost. I'm probably the second-most-expensive matchmaker in Denver after Rachel."

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What a fascinating and enlightening article. It's hard to be single, and Rachel brings great hope and determination to an otherwise frustrating and sad experience with dating. Rachel's positive spirit, her passion for others' happiness, and her smooth, easy manner are all elements of her success. But she's also a great, down-to-earth mom, wife and fabulous friend.

michelle g
michelle g

Hmmm . . . I found my amazing husband for FREE.


I think all that matters is that the people wanted a partner and the matchmaker got it for them. Does it matter how? She got the results. Shrug.

Jack Mackadoo
Jack Mackadoo

This is a fine story, Kelsey. But I will admit that I'm skeptical about utilizing the services of a matchmaker. I can see the pros and cons of it: Pros--especially with online dating, outsourcing the daunting task of weeding through hundreds of potential dating partners to find the ones that are a good fit is a huge time-saver, and a stranger can often advise you better than family or friends on what your strengths/weaknesses are with regard to dating capital. Cons--it's expensive, it's methodical, it's calculated, and the matchmaker's job is to get your ass down the aisle, but at the end of the magical fairy tale it's still you in the prom dress.

If a matchmaker's success is rated by how many couples she gets married off, then what makes her different than a chapel in Las Vegas? I would measure success by how many couples she matched who are in healthy, happy marriages after one year---five years---ten years.....


This is the most ridiculous use of an MBA from Harvard...not to mention the idea that we continue to put women in these horrific roles to "hunt" down men based on the very stereotypes we have tried so hard to get away from...shame on Westword for making this a cover story about a very shallow woman who has learned to capitalize on other people's need to find a partner


I find Ms. Greenwald’s business a bit appalling. People in the 1960s and 70s expended a lot of effort to break down discriminatory policies and to support and create opportunities for women to go to business school. It is disappointing to me that Ms Greenwald took the opportunity thus created to go to Harvard Business School and chose to spend it in this way. Isn’t she reinforcing patriarchal marriage, where the woman is the primary parent, disenfranchised and demobilized in deference to men in the political economy, and oppressing the children because that’s the only power she has? I am worried she is charging huge amounts of money to people who are vulnerable and who don't understand the ramifications of patriarchal marriage and that modern, two-earner, two parent egalitarian marriage is now available (and is especially widely pursued by Gen-Y and Millenial age men and women, but also by many in Ms. Greenwald’s Gen-X cohort). And she is training other women to do this. Is this kind-of like a cult?

It is interesting to compare Ms. Greenwald’s approach to that of some other women Harvard Business School graduates of her Gen-X era: Sheryl Sandberg and Gayle Tzemach Lemmon. Ms. Sandberg, Facebook COO, shares equally the unpaid work, responsibility and power of her home, including parenting, with her husband. And she married her good friend, by the way; Is it a coincidence that she is capable of being friends with men (and didn't need a matchmaker) when she has this more adult and responsible attitude? Ms. Sandberg also just served as one of the chairs of the prestigious Davos Financial Forum. Ms. Tzemach Lemmon, Newsweek editor and the author of the bestselling book “The Dressmaker of Kabul”, has done excellent reporting about businesswomen in places like Afghanistan and busts stereotypes that US warmongers circulate about the US needing to go to war to protect the women there.

Some of the most serious harms of the patriarchal marriage fall on the children; I gather Ms. Greenwald doesn’t really reach that issue. They range from abuse/neglectful/traumatic parenting by both men and women, high divorce rates, biological clock issues in the children of men who father children at older ages, and children having to take care of mothers who can’t stand on their own.

She says she has few successes in her business; are these serious flaws in her business model the reason?”


Western Civilization will be much better off when it returns to honoring the traditional family, with Husband, Wife, and children. All of these experiments with bizarre alternatives are proving to be failures. Worse of course is the single mother paid by the state to raise children without a father. That results in boys who are utterly without male role models, resulting in gang behavior, no work ethic, poverty, crime. And many women are finding that after wasting their childbearing years toiling in a thankless corporate world they are left with nothing, no family, and for some only grudging respect of the business world. Money can't buy you love in that case. The folly is in pretending that men and women are interchangeable and that God did not create men and women with unique characteristics, the melding of which in the form of the family, results in the correct situation for life, and for the world. Most of the time people like to point to one bizarre family they know that is good, such as two men, two women, or any other combination of people, and then extrapolate that to the bizarre conclusion that therefore the traditional family means nothing and any combination of people should work just fine for everyone. Thousands of years of history prove what is right. The current experimentation will prove to be wrong. Nature will win out in the end.


You don't "buy" love, in any case. I would suggest that if you think you can, you may not really know what it is?

I imagine these are scary times for people who have not adjusted to the progress of the 20th Century. Having women do things like go to Harvard Business School is particularly scary to people who have issues from the female-dominated childhoods that patriarchal marriage insists upon. If you are having trouble adjusting to being a real dad, a book many men have found helpful is "The Modern Dad's Dilemma" by John Badalament.

You are correct that nature will win out in the end, though: there is no God. That is a fantasy created by the dysfunctions of the patriarchal family, which is a stop-gap (i.e. temporary) invention created only because paternity could not be proven and disproven. Our political and legal system has not quite caught up yet, but it will soon. In the broad range of human evolution, patriarchal marriage and male monotheistic religion is but a blip.