Bethesda matchmaker Michelle Jacoby helps find people who click.

Photo credit: Erick Gibson

But there are some. There’s Carrie Keener, 35, a slim, green-eyed, goldenhearted first-grade teacher living in Bethesda who has never married, loves children, dogs and her work, has a great family and financial security. She looks like Tara Reid, back when Tara Reid looked like Tara Reid. Ordinarily, she could not afford Jacoby. But Jacoby has waived her fee for this experiment for Bethesda Magazine.

“I always have an excuse not to date,” Carrie says. She has had a couple of longterm relationships, though. One had to move and wanted her to come with him minus commitment. Carrie wouldn’t do it. “He was The One,” she says, a little regretfully.

“He allowed that to happen,” Jacoby tells her gently. They’re in Jacoby’s sunny Bethesda dining room, drinking tea. Easton, 4, watches SpongeBob in the next room, occasionally explaining the more intricate plot points to the ladies discussing love.

“I hate the beginning of dating,” Carrie says. “I like the comfortable part—seeing someone at their worst and realizing you still love them.”

Jacoby asks what worked for Carrie in the past. “He was extremely handsome,” Carrie says. “I know that’s not important, but—”

Jacoby interrupts: If it matters to Carrie, it’s important. “I’m like a man,” Jacoby says. “I believe the physical is so important.”


Carrie wants a family. Carrie wants a dog person. (“I have a howling shedder—and volunteer at a dog rescue. One guy said, ‘Dog hair!’ like it was a bad thing, and I was like, ‘Get out.’ ”) Jacoby asks Carrie for five must-haves and five deal-breakers. Carrie thinks for a long moment, then comes out with five at once: honesty, loyalty, compassion, funny, attraction.

The deal-breakers take her a lot longer. Jacoby says this is pretty common for women. Some of her male clients come right out with, say, nobody over 135 pounds. But while women may be just as focused on the physical, they don’t want to sound shallow.

“OK,” Carrie says. “Taller than me.” She’s 5-foot-8, so he would have to be 5-foot-9. “Dark-haired men, usually.”


Jacoby leans in, conspiratorially. “Ooh, I have a guy in mind for you! Now, religion, political views…?”

Carrie isn’t particular, as long as the person is easygoing about both. “Empathy,” she says. “I pass a homeless person, he gets my lunch. But how can you test for that?”

Jacoby laughs and offers to put something in her teeth when she meets a potential match for Carrie. If he tells her about it, choosing awkwardness for him over embarrassment for her, he’s a keeper.


By now, Carrie is more confident in voicing her hopes. “Nothing’s sexier than the guy at the party who’s in the backyard with all the kids, having the greatest time.”

Jacoby asks about the least-attractive guy Carrie has been attracted to. Balding? Not in perfect shape?

“I don’t know anymore. That’s my problem,” Carrie says. Maybe she was too picky before, maybe that’s what’s keeping her single.


Carrie’s ideal guy would come home, open a bottle of wine, watch a movie or go to a Capitals game. Carrie is at school 12 hours a day, teaching tutoring and working on her master’s thesis. “Is that weird, to ask for a guy who can drink a glass of wine when we get home? Oh, and I love to cook.”

Back to deal-breakers: Smokers? No. Recovering alcoholics? Carrie wants to say they’re OK, but her after-work wine ritual is an important stress-buster, and that could be a problem for a guy on the wagon.

Jacoby mentions that it’s easier to approach men when you’re looking for a boyfriend for someone else.


“Aaargh, I hate going out, and I always miss signals or I’m totally oblivious,” Carrie says, covering her face with her hands. Jacoby recently held a symposium on the art of flirting. “Go out alone,” not in a gaggle of women, she advises. And smile. “When you see a guy looking at you, if you’re interested, what’s the first thing you do?”

“Uh—I look down.”

“Don’t do that! Return the eye contact. Three or four seconds. It’s an invitation,” Jacoby explains.


Carrie protests that she couldn’t possibly.

“What’s the worst that can happen?”

“I’ll get rejected!”


It’s absolutely true. There’s nothing Jacoby can do about that. But she can make sure there’s a next guy.

“OK, you’re just going to tell me what I’m supposed to do, right? … It’s all in your hands. I don’t have to do anything! I love that.” Carrie looks giddily hopeful. Jacoby is smiling. It’s all in her hands.

The first match is at the Nest Cafe on Bethesda Avenue with a 33-year-old lawyer whom Carrie describes as a full-time cutie patootie. “When I saw him, well, I like a man with a lot of confidence, and he has a LOT,” she says. “I love that slowness when someone really listens to you, and that big smile.”


She hates first dates, but she’s excited about this one. “He was easy to talk to, we joked a lot about first dates. He’s a kidder, laid-back.”

The date lasts almost four hours. She calls Jacoby afterward, really excited. Later Jacoby tells Carrie that the lawyer “really liked her as a friend.”

Carrie now wonders if it “went into the friend zone, got too comfortable. We made fun of relationships. Maybe I steered it away from feeling romantic.” She goes through it in her head, trying to figure out what she did wrong.


“She wasn’t showing him how wonderful she is in the first impression,” Jacoby says. She fixes the lawyer up on another date, a freebie, to thank him. “He was a gentleman and made me look good.” The lawyer and the freebie end up dating for some time.

Next up for Carrie, at Green Papaya on Elm Street: a 40ish, outgoing single dad who wants more kids. He’s very nice, and obviously loves children. But Carrie doesn’t feel the spark. She gives him her number to be polite.

He wants to see her again. But after his debriefing with Jacoby, he doesn’t call.


“Sometimes you have to put people together to see what happens,” Jacoby says. “It’s like cooking: You throw things together and see if it tastes good.” It’s worth noting that, as she says this, she is eating brussels sprouts and quinoa.

Date No. 3 for Carrie is a 30-year-old D.C. power broker who has her “laughing out loud. He’s younger, goes out more than I do, is easy to talk to. I could see myself being friends with him.” They talk for hours after a Sunday afternoon date at Jaleo. Carrie decides she’ll go out with him again.

“He’s a very particular client,” Jacoby says. “And he was impressed with Carrie.” She gets the idea he’s going to call Carrie, but he never does.


It turns out that even $10,000 and a great matchmaker can’t make dating not suck. Maybe they just make it suck less.

Carrie’s keeping busy these days. Seventeen of her 25 students this year are boys, and getting 6-year-old boys to behave seven hours a day would make anyone break into a cold sweat. “You use completely different strategies with boys,” she says. “I’ve fallen in love with boys this year.”

Her master’s thesis involves taping her classes and analyzing the tapes to see what she could be doing better to motivate struggling readers. Perhaps out of habit, she goes over her dates in her head, trying to figure out what she could have done better.


“How could I go out with three different men and not have a [mutual] connection with any of them? What’s wrong with me?” she asks.

She thinks back to her five-year relationship with “The One.” Her best date with him: They grilled steaks, watched The Sopranos, exchanged back rubs. When that relationship ended, “it turned me into someone who puts the wall up.”

So at 35, Carrie is starting to plan a future in which she can be happy without a romantic partner. She’ll adopt kids. She’ll get by without a joint checking account. “I don’t bank on getting married,” she says. “It would be a bonus. If you can have love in one area of your life, unconditional love—well, that’s the most I could ask for. If it doesn’t happen—well, there are so many people who don’t have what I have. I have everything. I have family.”

Love seemed so near and inevitable in Jacoby’s sunny dining room. But sometimes love is a zero-sum game in which every happy couple means fewer options left for the rest of us.

There were just three dates. Perhaps if there were more…“It just takes one,” Jacoby says.

In her moment of greatest optimism, Carrie exulted at putting all of her hopes in Jacoby’s hands, but of course you can never pin all your hopes on someone else. A matchmaker can’t do anything to ease that aching, vulnerable moment when a stranger decides, life being short, that it’s not worth the time to get to know you better. And a matchmaker can’t necessarily tell you what’s wrong with you, even if the answer is—as it often is in matters of the broken heart—nothing.

Since this story was written, Jacoby fixed Carrie up with one of her clients. They really liked each other, but the spark didn’t happen. Jacoby still has her eye out.

Update: After the article was published, Jacoby continued to “match” Keener. “I really wanted her to meet a great guy,” Jacoby says. The sixth match ended up being the right one. Keener was married at the end of October 2011 to lucky number six.

Rachel Manteuffel is an actress and freelance writer who has written for The Washington Post Magazine.