The first step to creating a business out of love is marketing it. Immediately after she finished boot camp, Richards bought a domain name, created a website and worked with a company that specializes in search-engine optimization to make one of the highest-ranking sites of its kind in the area. From there, she chose a clientele niche: For matchmaking, Richards helps wealthy men in their forties through sixties find women who are twenty years younger and a ten out of ten. "Tens don't really exist," Greenwald says. "But nines do."

From there, she synced her brand with Twitter, where she is @denverhitchette, and Facebook, where her company is called Happily Ever Afters. All of her prices are based on Greenwald's fees, and she works month to month with no contracts because Greenwald structured her own business that way. Richards oversees no more than five matchmaking clients at a time, a recommendation that meshes with Greenwald's push for low-volume, high-dollar business. But in the year that she has spent adapting her training, Richards has developed her own rules, too. She often pre-dates women herself to weed out unfit candidates, and her matchmaking services extend to shopping for her male clients and even helping them clean up their electronic footprints. "I don't guarantee a number of dates, and I don't show men photos of the women they're dating, because I want them to trust me," Richards says. "I don't give them contact or name info until right before the date, because I don't want them Googling each other. I have done this enough to know what is best for them, and all they have to do is let me go."


The United States currently houses more single people than any country outside of China and India. Roughly 40 million Americans use online dating sites, and that industry is expected to reach an annual worth of $1.3 billion in 2013. Although many assumed it would be a death knell for yentas, the rise of online dating actually boosted matchmaking in two distinct ways. First, it made it okay to outsource your love life. In the sense that you can write exactly — exactly — what you're into on your dating profile, love is no longer a private experience, and neither is your quest for it. "Today, if you're not online, you're not single," Greenwald says.

Second, people become frustrated with online dating — and that's when a matchmaker's services prove invaluable. That massive process of weeding through potential mates is exhausting, and some of the people winking at you turn out to be married or creepy. It's a tough job to tackle alone, and it's an embarrassing one to mismanage.

"I once had an Orthodox Jewish girl I was working with in New York, and she had been dating someone for four or five dates and let him sleep over," Greenwald says. "Well, the next morning he has to go to temple, but it's Shabbat and it's too far away for him to go without using technology, and he didn't have his tallis, his prayer shawl. She runs to the bathroom and is texting me because she doesn't know whether it's him freaking out about sleeping together or about his tallis."

When Greenwald peeks at her cell phone, the move is subtle, as though she's just reaching for a fork and accidentally encounters her BlackBerry. In case of dating emergencies like the tallis incident, she and her disciples keep their cell phones turned on and are always available to tackle romantic problems as they develop.

A typical date-coaching session with a female client covers a strict regimen of training, refinement and blunt honesty. Before even starting out with a new date-coaching customer, though, Greenwald asks the woman to request a minimum of six letters from friends, family members and ex-boyfriends, explaining why this client has not yet found love. After that, a client will fly in to Denver (most of them are from New York), where Greenwald will book her into a comfortable hotel and then wake her up at eight the next morning to have her makeup and hair done in Cherry Creek.

From there, the client will visit Marea Evans, Greenwald's go-to photographer, to have flattering photos taken for her dating profile. All clients are required to purchase a brand-new push-up bra before being photographed, and Greenwald approves their wardrobe options before the photos are taken. The rest of the day consists of one-on-one date counseling with a short lunch break, during which Greenwald actually stages a pretend date.

All of this work takes time and expertise, and Greenwald encourages the matchmakers she trains to charge heavily for them. Some clients do not even trust matchmakers who do not approach the expensive end of the scale, she points out. The issue of price is frequently debated at her boot camp, though most followers elect to follow Greenwald's scale, or at least an approximation of it. But Boulder dating coach Heidi Wicks has elected to ignore it.

"My feeling is that everybody deserves love, not just the wealthy," Wicks says. "There are a lot of business models that only cater to the wealthy, and that just rubs me the wrong way. I want to be available to people with less money, but I still want to make money."

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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.