The book's reviews were glowing. "Want a spouse? Read this book!" proclaimed Fortune. The Observer raved that "Greenwald is the hottest thing to hit the dating scene since Sex and the City." The New York Post praised her pragmatism. Requests for help overwhelmed her inbox. Soon Greenwald expanded her business beyond merely writing about love to actually working as a matchmaker for male clients and as a dating coach for women.

Greenwald continues to write about love, though more briefly and regularly, for the Huffington Post, on dating websites such as, and for other sites including YourTango and GenConnect. She followed up on Find a Husband After 35 (now out in a new paperback version) with 2010's Have Him at Hello; together those books have pushed her career as a matchmaker for millionaires and earned Greenwald a spot on the NBC dating reality show The Match-Off. She has been featured on The Today Show, CNN, ABC Nightline and The Early Show, and in the pages of the New York Times, People, Fortune, the New Yorker, Cosmopolitan and Glamour.

Greenwald cannot begin to fill the country's matchmaking needs on her own. So four years ago, she developed a series of workshops to train others who want to enter the multibillion-dollar industry. At exclusive and demanding boot camps, she now spends two days a year instructing these acolytes in the secrets of successful matchmaking. And in 2010 and 2011, Greenwald delivered the keynote address at Matchmaking Pro's national conference, which is devoted to supporting a career that was not even a viable financial option when she took it on.

"At that point, when I started, there were probably only about ten full-time national matchmakers in the United States, so it was really off the radar," she says. "Online dating was just beginning, but matchmaking has become incredibly popular as a living since then."

The only reason she turned down a repeat performance at this year's national conference is because her eldest son's SAT is scheduled for that day, and she didn't pick this career so that she could ignore her family.

In college, Greenwald had more first dates than any of her peers. Today, she says, she is offered more business than most of her Colorado matchmaking peers, though she rejects roughly 80 percent of those inquiries. Greenwald's matchmaking and date-coaching strategies continue to center on the same ones she used in the business world: branding, packaging and niche marketing. "Rachel is an amazing businesswoman," says Jaime Richards, one of Greenwald's most recent disciples. "She doesn't even bother with anything that isn't profitable."

The media has dubbed Greenwald "The WifeMaker." But she has another word for her career: "magic."


The opening scene of Hello, Dolly! finds the title character walking across what appears to be the entirety of Yonkers, New York. Her goal is to build a client base, which the matchmaker then spends the rest of the movie systematically turning into couples. Dolly Levi is sassy, bossy and almost omniscient in her quest. She is also Barbra Streisand, so this scene, though classic, has absolutely nothing to do with Greenwald's business. Even Millionaire Matchmaker's Patti Stanger has yet to be commemorated in song, despite spending five seasons dispensing highly quotable advice to people with high net worths.

But Dolly, the meddling older lady, continues to be one of the two most prevalent matchmaker stereotypes; the other is the frigid bitch. Stanger fits somewhere in the middle of this spectrum, but Greenwald avoids it entirely: To her, matchmaking is a serious business. "It's a career everyone thinks they can do, especially women who think they have been doing this all their lives with their girlfriends," Greenwald says. "People think they're just going to go around and fix happy people up all the time and it's all joy and flowers, but that's not true."

Strategic matchmaking is an expensive process, and even in these tough times, people do not hesitate to pay thousands of dollars for the right modern-day yenta. Time reported a steep rise in business for high-end matchmakers last year. (It also reported that in 2009, the matchmaking industry was one of the Council of Better Business Bureaus' top industries for complaints by consumers.) "When you're faced emotionally with loss all around you — loss of finances — all you want is love," Greenwald explains. "People are not going to Starbucks to spend $4, but they're spending $10,000 on a matchmaker. It's like everything in the world is crashing around you and you just want to be in love."

Although she admits she is "incredibly expensive" — her date coaching can cost as much as $2,000 to $5,000 a day — Greenwald declines to reveal the cost of her annual boot camps (the next one is scheduled for April in Denver). "Price is usually its own screen," she says. "People who are really serious about starting their own business self-select. Two-thirds of the people, I never hear back from again. If people have to ask how much it costs, frankly, it's not for them."

There are other options, of course, and the tools of the trade vary in direct proportion to the seriousness of their buyer. Matchmaking Pro, for example, sells a boxed notebook starter kit for cheaper beginners.

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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.