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Feminist Practices

Can a Professional Matchmaker be a Feminist?

Photo by Jana Sabeth, Unsplash

Fourteen years ago, I got a job as a matchmaker at a high-end dating agency in downtown Toronto. It was awful. Once I learned how the company operated, my dreams of putting perfect matches together were shattered. Our members had paid ridiculous amounts of money to join our closed network; they could only be matched with other people who had also paid to join. And as far as I could tell, most of these members wanted nothing to do with each other. Salespeople charged outrageous and whimsically fluctuating prices, and the company embraced dishonesty as a policy. No wonder our clients were always angry.

As a “dating consultant” in the Matching department, my job was to try and convince these disillusioned people to say “yes” to each other. I heard “no” a lot and spent far too much time making notes on people’s disappointment with our company, and more hauntingly, their loneliness. It was frustrating being unable to help my clients, and I was disgusted by the sexist sales structure. Women routinely paid three times as much as male clients—often well over $10,000 for four to six “introductions,” which our company (and most traditional matchmakers) defined as the exchange of contact details. I learned that this is the norm for “traditional” matchmaking and dating agencies.

Still, I enjoyed putting people together—especially the clients who hadn’t heard from us in years—and I managed to make some good matches in that wasteland. I also learned some valuable things about human nature: People really cling to stereotypes when it comes to dating, even if they seem enlightened about everything else; most people would rather hear the truth than a comforting lie; plus, everyone—and I mean everyone—self-identifies as youthful, with a good sense of humour.

But most of the time, I was ashamed of the way the company forced me to lie and stall people. I quickly tired of fielding justifiably angry phone calls. I actually began advising my favourite members that they would be better off spending their time and energy on a dating site.

That company folded—a victim of the 2008 economic crisis—while I was on maternity leave. I hadn’t imagined that I would ever go back there, but I was surprised and disappointed that I never had the chance to say goodbye to my members. Fortunately, a handful of them had given me their email addresses. In 2012, when I launched my own business, Junia Matchmaking Services, they became some of my very first clients.

Ann Marshall, founder of Junia Matchmaking Services

I operate almost exclusively online, using existing dating sites. I consider myself a matchmaker, but also a dating coach and online dating surrogate/concierge. Essentially, I am e-Cyrano. I’m often better at writing about you than you would be yourself. I write dating profiles. I also curate and edit my clients’ pictures. Sometimes I even take the photos myself. I then set clients up on dating websites like POF (formerly PlentyOfFish) and Match, where I run their profile(s) entirely. I’m the online version of them.

I get the irony in what one of my clients said about my service: “You don’t realize you aren’t being yourself until you are finally allowed to be.” Bonnie, 55, is living with the man I found for her on POF a little less than a year ago. “I was looking in all the wrong places,” she laughs, admitting that she was stuck on “eye candy.”

My services are particularly valuable to women, although I serve clients of all genders, including non-binary people. Most people outside of my industry aren’t aware that men consistently outnumber women on dating sites and apps. This gap persists because so many women are hesitant to “put themselves out there.” Many women hire me because they’ve heard of or had a “gross” experience online. I’ve been using dating sites professionally for eight years, and I know a lot about the privacy settings, which keeps intrusive messages to a minimum. I immediately delete offensive or sexual remarks and block users who display any impatience. I’m always amazed by how many people think 24 hours is too long to wait for a response to a question about the last book you read.

I also pay very little attention to the unsolicited messages my clients receive; rather, I spend my time searching the websites for prospects who meet my client’s criteria, running those candidates by my clients, and then sending friendly messages to any matches a client approves—signed with my client’s name. If the conversation goes well, and the client is willing to meet the person I’ve been talking to, I will set them up on a first date.

My clients don’t wait to hear from the people they might want to meet, because I am starting that conversation for them.

My mission is to make my services accessible and affordable to anyone who wants to use them. I have virtually no overhead, working from an office in the basement of my Guelph, Ont., home. Many—but not all—of my clients would have difficulty finding representation with a traditional matchmaker, including singles disadvantaged by intersecting forms of oppression. I often work on behalf of older women, LGBTQ+ people, people with disabilities, and people of colour. My regular clients pay a monthly fee of $475 (including HST), but I offer services on a sliding scale for seniors, students, artists, and anyone else on a limited income or facing financial hardship. I never turn away anyone I think I can help.

I work with clients month by month until we’ve found someone they want to keep seeing—or until they’ve gained the confidence to work their profile for themselves. I don’t always get to hear the follow-up story. My definition of “success” is pretty fluid. Marriage isn’t always the goal. People come to me for different reasons. Some haven’t dated in 40 years and they just want to learn the “ropes.” Some want to find a lifetime love but never live together. Some just want to have sex again, with or without love.

They also come to me at all stages of life; my youngest client was 24, and my oldest was 77. That client, Georgina, is getting married to a 73-year-old in June. A lot of former clients keep in touch. I get invited to at least one or two weddings a year—the ones where one spouse has told the other of my role. I can also take credit for about a dozen babies so far.

Right now, things have definitely slowed down as a result of the COVID-19 crisis. Almost all of my clients have chosen to put things on hold for the moment. It’s hard for people to imagine paying hundreds of dollars to “meet” someone they might not actually meet face to face for a year. But it’s also an excellent time to be online dating, for that exact reason. You can be as picky as you like right now! And, well, the only safe way to search for love now is online.

But nudging matchmaking into 21st century reality isn’t only about being online. While the industry remains heavily burdened by patriarchal convention, there is a growing number of matchmakers willing to stand up and be counted as feminist. Many are members of a large Facebook group, “Professional Love Connectors”. Tammy Shaklee, an Austin, Texas–based matchmaker who runs the company, H4M, is a “straight ally” who exclusively serves the LGBTQ+ community, providing one-to-one introductions for clients all over the United States. She’s also committed to making social justice a pillar of her work, and H4M donates thousands to LGBTQ+ charities every year, while encouraging its mainly affluent clientele to do the same.

Another group member, Amy Van Doran, says “feminist” is the word that started her career. She is the founder of New York City’s Modern Love Club, and defines a feminist matchmaker as one who “enables women to have as much agency in the dating process as their male counterparts.” She runs her “hyper-curated” old-fashioned matchmaking business out of an East Village gallery space in Lower Manhattan. She fills her company’s Rolodex by interviewing 54 people a week during “office hours,” and hosting regular art openings and events in the evening that draw an eclectic mix of artists, professionals, and other NYC singles. There’s a dedicated “free dating spot” right outside the storefront in warm weather months, for visitors who want to get to know each other on the premises. From that potential pool, she agrees to arrange matches for only “16 remarkable clients a year.”

Fees are hefty, starting in the $20,000 range, and Van Doran only takes on those she really feels she can help—and who can obviously pay. But that doesn’t mean the standard cis-het, white professionals only—she’s more interested in what’s going on inside a person’s head. Van Doran prefers to match “really interesting people, with a lot going on intellectually.” In her experience, the more unique, original, and engaging a person is, the harder it is for them to find love in the wild. That’s where she comes in; not just putting two people together, but convincing them to take a leap of faith or see potential in someone they are inclined to dismiss.

She cites the recent match of her yoga instructor in New York City with a man she met at Burning Man who lived on a commune in Oregon. “I was like, ‘Listen. Hear me out. This guy is your guy.’ It was so weird, but it was just obvious.” Her client listened. He left the commune. They now live in upstate New York, and they’re getting married.

Van Doran says she helps her clients free themselves from “thinking that you have to date a certain kind of person.” She believes criteria such as matching incomes, racial preferences, and even height parameters are obstructing the most important part of the matchmaking process. “We need to get away from all that and just ask, ‘Does this person make me happy?’ Everything else is going to change.”

One challenge of matching extraordinary people—and women in particular—is that they often expect a partner to bring exactly what they offer to a match, in terms of ambition, education, or material success. Van Doran challenges her clients to stop thinking that they have to date someone with a very similar lifestyle and career. “You don’t need two people who are running at top speed all the time.”

In my own matchmaking work, I have discovered that while complementary lifestyles can be extremely important, opposites who don’t tick all of each other’s boxes often make good matches. Van Doran and I both agree that the most important thing in finding a good match is paying attention to how a person makes you feel. Do you feel heard when you are talking to them? Do they make you laugh? Do you smile when you think of them? Are you excited to see their name come up on the phone? Would your best friend, your grandma, or your dog get along with them? Now that’s a match!

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Butchers, Bakers & Changemakers: The Nightwood Society

A Nightwood Society panel discussion on the future of food with Michelle Battista, along with Kim Malek of Salt & Straw, Alison Wu of Wu Haus, Nong Poonsukwattana of Nong’s Khao Man Gai, and chef/food activist Arlyn Frank of Platano Rising, put on by Cherry Bombe, a magazine devoted to women in food.

As the saying goes, a woman’s place is in the kitchen—that is until money, fame, or a coveted Michelin star is at stake, at which point it can become a male-dominated space pretty quickly. Foodie utopia Portland was no different until an industry outsider named Michelle Battista decided to challenge the culinary boys’ club. In 2014, the designer and marketing entrepreneur with a passion for food brought together a group of women with diverse talents to create what she describes as “a safe place for women in culinary arts.”

Enter the Nightwood Society. The eclectic group—ranging in skill set from butchers and bakers to florists, writers, and visual artists—conceived of a food-based creative incubator to nurture women entrepreneurs striving to find stable footing in Portland’s vibrant and competitive culinary scene. They toiled in a variety of traditionally underfunded areas—live music, cooking classes, immersive dining experiences, catered events, art installations—but believed by joining forces, they could create something special and sustaining.

Battista teamed up with friend and associate Kati Reardon, a product management specialist for global brands such as Nike, Columbia Sportswear, and Banana Republic, to raise the capital to lease a 3,000-square-foot event space in the city’s inner NE business district, where they could bring together food, art, design, and social consciousness in a delightful blend of community activism. “So we decided we could do this, and do this in our own way,” says Battista, “and it could be all women.”

Indeed, Nightwood Society created a women-focused supply chain, from farmers through to sommeliers and chefs. For capital, they turned to non-traditional investors such as women’s accelerators and financing groups. Supportive, like-minded men were welcome to contribute.

But Portland, as Battista describes it, is a finicky market where the average restaurant has a life expectancy of about two years. Those that survive face constant scrutiny over the minutiae of their menus. Was this free-range chicken fed on pesticide-free grains and seasoned with fair trade salt? Is your house kombucha small-batch or just craft?
Nightwood Society overcame the odds and found its way to a stable source of revenue by becoming a go-to space for community groups that share their interests and values in social justice, diversity, and equality. They have hosted events, leased space and catered for women’s outreach groups, non-profit organizations, and even Oregon’s governor, Kate Brown.

A Nightwood evening event.

All that didn’t come about by happenstance. When Battista moved to Portland after going to school in New York, she was shocked by the city’s whiteness—and its long history of racism and exclusion. She knew Nightwood would never reach communities of colour organically but would have to reach out specifically to historically oppressed and overlooked groups. Says Battista: “Nightwood is the hub of a community I built and curated intentionally with a lot of time and attention. We ask, who do we want to reach out to and how do we vet their values? Without shared values it isn’t going to work.”

The outside-the-box business model has also built strength by sharing resources. The range of activities at the Nightwood Society can be eclectic: cooking and charcuterie-making classes, weddings, political events, public speaking classes, and outside catering gigs. Beyond a skeletal staff, most function as contractors and freelancers, posting shifts that others sign up for and taking shifts based on schedules and skill sets. The arrangement suits the ebb and flow of the business and the lives of the people drawn to such a dynamic, artistic enterprise. Says Battista: “Everyone works when they want. No one’s ever grumpy [as] they have other jobs.”

The collective is structured as a limited liability corporation with two legal owners, each with a clearly defined equity agreement. Members can buy into the for-profit business. Leah Scafe, Director of Experience, and Sarah Schneider, “Kitchen Queen,” have acquired a partial ownership, which comes with more decision-making power and autonomy.

But the vast majority of the dozen or so primary members involved have a part-time association with the collective, using the space to grow their business, augment other income, and network with supportive, like-minded entrepreneurs. The model enables Nightwood to be flexible, inclusive, and resilient. It supports growth via diversification rather than simply volume. And it allows them to scale their business sustainably through ebbs and flows of a fluctuating economy.
To Battista, Nightwood’s fusion of food, art, and activism is natural. “I’m a designer by trade and I have a design agency; I’ve always been obsessed with connecting sensory things.” She says she doesn’t just love food and the craft of making it, but the whole experience of food, including the atmosphere of the surroundings and the company at one’s table.
Battista urges people looking to emulate the Nightwood model to build a strong team. “There is a moment when you just have to jump in and be on the ride and use your best assumptions and experience to make it happen.” But it helps, she advises, to have a mentor and to ask for guidance when you encounter something you don’t understand. Then comes the task of building a team that shares your vision and values. “Without the right people to believe in and help you execute your vision, then your vision is only an idea.”

After that, the rules for taking something on, she says, are pretty simple. “Lead with the values always and don’t compromise. This is your compass,” says Battista. Evaluate proposals based on whether they move the venture forward, and whether or not they serve everyone’s best interests, as well as your vision and mission. Make sure what you do stays on brand. Remember that you can’t say yes to everything.

But how does that clear-eyed vision translate into the effective operation of a for-profit enterprise that offers charcuterie classes and public speaking classes, as well as hosts political events and weddings, all under the guise of a cutting-edge restaurant? Pretty effectively, says Battista, albeit with a lot of individual trust, coaching, and business mentoring. The entire staff meets just every two weeks to handle the logistics of the organization. Outside of that, Battista makes a point of not micromanaging the members. The goal is to find motivated innovators with a unique vision and nurture them with resources and opportunity.

“And then,” Battista says, “we let them grow.”

To learn more about the Nightwood Society, visit

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