Bethesda matchmaker Michelle Jacoby helps find people who click.

Photo credit: Erick Gibson

“My dream is to find the 5-foot-2, socially awkward, not-attractive guy who has wanted all his life to find love.” The petite, successful Bethesda businesswoman smiles as she says this, knowing how silly it sounds, how naïve and romantic she is to set such a lofty goal. Michelle Jacoby is dreaming not of a boyfriend, but of a client. As a matchmaker, “I’d like to be so good at this I can take anyone as a client,” she says. “Like being a doctor: When you become the best, you take only the challenging cases.”

Jacoby is in love with her job. A year after launching DC Matchmaking, she has 15 high-paying clients and a database of more than 700 people hoping to be matched with them. She walks up to promising strangers on the street or at the Motor Vehicle Administration and asks if they’re single. A successful first date will send her dancing around her living room, even though she’s hearing about it secondhand. Jacoby is 44 and pretty, reminiscent of Dr. Lisa Cuddy on House, a single-but-dating mom of four so unafraid of matchmaker clichés that she’ll throw out some Yiddish now and then.

Her service costs $20,000 a year—half upfront, half a finder’s bonus after 12 months in a successful match. It’s a fantastically confident business plan, and though “success” is too variably defined among her clients for statistics to mean much, her first client joined last July and has been in a relationship for seven months. Even in the midst of an economic recession, she has ceased searching out clients—they’re coming to her. Her waiting list is 20 deep. She started the business with about $5,000—laptop, Web site design, certification with the Professional Matchmakers Association, becoming an LLC—spent just $120 on advertising for fliers she barely used, and has never been in the red. She works from home in pajamas in the morning, and glitzed-up and in high-heels at hotel bars and steakhouses at night. The men she dates herself have to accept that she might get up in the middle of dinner and go talk to an eligible bachelor, and that at parties she’ll end up giving out her cards to single men.

The Washington, D.C., area is rife with high-end matchmakers and dating services, catering to a well-off, busy clientele who don’t enjoy the bar scene and don’t have time to meet enough people to tip the dating odds in their favor. More than a dozen companies here specialize in romantic headhunting, ranging from one-employee offices to those with staffs of 25. Prices run from $1,000 a year to so much that if you ask, they’ll tell you they probably aren’t what you’re looking for. Their clients are frustrated with conventional singles scenes, or high-profile enough that an ad on a dating Web site would endanger their job, or working so hard and playing so hard that they never meet anyone new. They hire people to find them jobs, clean their houses, babysit their kids, walk their dogs—so why not to find them love?

A stay-at-home mom for 17 years, Jacoby started on the path to her career five years ago with a business selling personalized children’s toys online from home. At first, “no one found the Web site,” she says. “I became obsessed with search-engine optimization.” With some tweaks, “the site became the No. 2 hit when you Google searched ‘kid gift’—above ToysRUs. I had to turn the Web site off. I didn’t want to be in my attic making books all day.”

So Jacoby started doing consulting work in search-engine optimization, with the business again outgrowing her enthusiasm for it. What else could she do with her understanding of what makes people click? She optimized an L.A. dating coach’s Web site in return for some tricks of the trade. Within a week of setting up her own Web site, she was on page one of a Google search for “DC Matchmaker.” The domain name,, helped.


If you get Jacoby interested in you as a client, and if your background checks out, it’ll go something like this: She’ll meet you for a two-hour get-together at a place like Barnes & Noble’s coffee shop or the Daily Grill in Bethesda. She’ll ask about your hopes and dreams, your history, your deal-breakers, then give you her business philosophy and sales pitch. She’ll take no notes, to put you at ease. If you sign up, you can pay in installments if you like.

The laptop comes out at the second interview, when she figures out more specifically what you have to offer, what you want and what’s standing in your way. She’ll ask for pictures of exes and people you find attractive, especially those not everyone would find so hot. She might advise you to cut your hair or give you flirting pointers. Then she begins searching through her database, through friends, through social networks.

Jacoby calls this the part when she “dates for you.” All the legitimate soul mate concerns come out that would be impolitic to ask about on a first date: How soon do you want kids? Are you a pro-life libertarian? Are you willing to relocate? Are you a natural redhead? Would you convert to Buddhism for the right person? Can you imagine life without at least three large dogs? Could you kiss a non-vegan? How often do you really work out? Really? Do you like neck tattoos on women? That way nobody wastes time being attracted to someone who voted for Ron Paul in the last election but doesn’t mention it until the fourth date.


Then you get a first name, an age, a brief description, a time and a place—usually dinner at a restaurant close to the woman (so far all of Jacoby’s matches have been heterosexual, though she says she would love to match gay people, too). You don’t get pictures, last names or phone numbers. Pictures, Jacoby says, are distracting and generally inaccurate, and since Jacoby meets everyone she sets up beforehand, she judges appearance herself. Last names mean Googling, Facebook and pictures, again distracting. And Jacoby makes the reservations so nobody gets lost in I’ll-call-you-did-you-get-my-text neverland.

You meet. The man pays, the first time. And the person fires up your neurons, or not.

Jacoby debriefs you soon afterward. He has bad breath. She wouldn’t stop talking about the bad day she had at work. He had me laughing out loud. I just didn’t feel that spark. I want to see her again. He didn’t seem interested. I got a friendly vibe, nothing more. She is exactly what I said my type is, but I don’t think that’s my type anymore. Your date is debriefed, too. And Jacoby packages it all so it’s easier to take, and gives it to you.


One client hates waiting around for the check after a meal, but didn’t realize his habit of asking for it as soon as the food was finished made his dates think he wanted the evening to be over quickly. Now he knows.

Another client sniffs and clears his throat often as he speaks, to the annoyance of one date. The next date was forewarned, chose to date him anyway and had a wonderful time.

A female client can be wildly attracted to her date while seeming indifferent, and now she knows how to indicate interest.


And nobody has to wonder why he doesn’t call. Jacoby will tell you. No guarantees it won’t be “I just didn’t feel any chemistry.”

In the movies, you can tell two people are supposed to fall in love because they’re conventionally attractive, with wacky friends and a tendency to get into embarrassing situations. Men are architects, and women work for glitzy magazines or teach small children who give adorably wise advice. In real life, there just aren’t that many guys who look better with their shirts off, and there aren’t that many slim, green-eyed first-grade teachers with hearts of gold.

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