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One hundred cups of coffee with 100 men.

I got the idea from a lawyer friend, who married a handsome furnituremaker in Maine, a man who owned more books than she did. "Sometimes," she said, "I met three a day. You only need 15 minutes." It took her two months. She quickly lost count.

After six months, I am at four.

We meet in a coffee shop parking lot. He springs out of his enormous red convertible, more like a boat than a car, and thrusts into my hands a fat library book. He looks ten years older than his photo and roughened, like someone has taken the smooth young version he posted and rubbed sandpaper over it. I stare at the book he's handed me, turn it over. It is a book of ideas and complaint. He is ranging around the parking lot on foot—big loops. Why is he ranging around the parking lot? Why am I holding a fat library book? "Finally," he says, rovering up to me, beaming. "Finally someone in this godforsaken place gets me." I kneel down, set the book on the pavement, pretend to tie my shoe.

The next man wants to go out again. I tell him about the coffees. He wants to know what number he is. "I want the T-shirt," he says. "Number X, with the cup, you know. That's what I want." He pats his front. He says he wants to be 99. He, too, has books, paperbacks in his backpack. Two backpacks. One is his office.

I feel so bad for them all. The man with a part in a play who could talk of nothing but the play. The play is his life. Both will start soon. The man in white kneesocks and black sneakers who chose a coffee shop across from the mental institution. It was very distracting. The whole time he talked, I kept trying not to think he'd come from across the street on a pass. Then, when I talked, at the end, I felt I was the one on the pass.

The chef/Hemingway aficionado/sea captain (age 53, two kids at home, blue eyes) who said he would be divorced but the economy was really bad and he couldn't do that to his wife just yet. She had a boyfriend. He was excited about dating.

It's like going to the pound and I am a nice dog from some other pound.

I felt afraid one time. He yelled, stood, holding his coffee aloft in the Buzzatorium, "I'm not a loser! I'm not a loser! I do not think I'm a loser!"

I feel forensic. I feel I should be getting paid, because this feels hard, like a job, all these coffees. And I have to get specifically dressed for it and leave my house.

They behave as though on job interviews or in sales positions, leaning forward, pitching. Maybe it's the caffeine, but the men do not shut up. Not nervous-talky, like a girl gets, but sales-talky, rushed, forceful, boasty. They have a few prepared questions, but they aren't wanting the information. They're checking boxes off. Asks questions. I'm talkative, and I can't get a word in edgewise. They talk for 30 minutes and I wonder how my friend kept it to 15. She lives in New York. In the Midwest, everything is slower. I listen too much. I need exit strategies. I need less hope. In the Midwest, we're shadowed by hope, enveloped by it.

Part of me wants them to keep talking; it's similar to reading a mediocre novel. I know I'll never finish, but I can't quite put it down. I know it won't get better. Can it get worse?

When I stand up to say goodbye, the men say, as people do when they've felt listened to, "Wow. You are a great conversationalist."

My friends are married people and stunned. "Why are you doing this?" "I could never do it." We say this same thing about tragedy, as though we have a choice. About wheelchairs and Down syndrome babies and cancer and missing limbs. Looking for love isn't a tragedy or a defect. It's a situation.

I'm doing this because I've been divorced three years and I haven't had a single date. No one has asked me out. I called the single father on my street before Christmas and asked him to go out for a drink. He said he didn't have any money right now.

My friends think I am trying too hard. "Stop trying and then it will happen!" "When you give up, that is when it will happen." They think I am so happy alone and I will not admit it. They have also suggested my standards are too low (the mechanic/hunter/libertarian who cursed in every single sentence he uttered) and too high (the baker who was thrilled to talk about gluten-free, who compared my body to that of a supermodel's. Whom I didn't want to see again—he had so many kids, a long commute, and byzantine ice hockey commitments).

My friends claim they can't imagine dating. If their husbands die, they say, they will make it alone. They pat their mates when they say this. They seem not madly in love but madly in small vague terror. I am helping them remember the good parts of marriage after a long, crabby day.

It's funny to me how many of the divorced men from Match say to me in conversation, "my wife." How much they talk about the lives from which they have been fired. As though I am a babysitter, guy, shrink, or nice wall.

Fed up with men's ads "seeking women age 18–[one year younger than whatever age they are]," I change my profile. I say I am looking for a man age range 18–41; I'm 42 years old. But my friend who met the furnituremaker says it isn't funny. You can't sound bitter, she says. You can't make a commentary; this isn't the time to make a point.

My friend Ellen met three gorgeous millionaires on Match. All wanted to study Buddhism with her and ride bikes with her; she picked the cyclist from Italy, who is ten years younger and crazy in love with her. "It's not like dating in your 20s," she told me. She says I need to be in my 50s to really do this right. "You're at just the wrong age," she said.

I do not know if dating in my 20s was like dating in my 20s. I was pretending to be a person similar to myself. The pretend person was much better and much worse than my true self. I had no real beliefs.

Almost a year later, I've made it to a couple of dozen.

Number 31 has, he says, simplified his life. "So tell me your life story in 20 words or less," he says, and I do, and he talks for the next 25 minutes, leaning forward, elbows on the table: his financial statement, his business plan, his recovery program, four children, his "wife." A man pushing an empty wheelchair can't get past our table. My coffee date doesn't see this, because it is taking place behind him and he is talking to me about the $3 million house in Aspen and how it's good he doesn't have it anymore. I stand up, pull the table a bit. The coffee date sees how, moves chairs. The man pushing the wheelchair still struggles. The chair is like a prop—something he has never seen before, much less used. Finally, he gets past us.

"Do you mind getting the door?" he says to my coffee date. My coffee date rushes to the door, gallant. "And the next door?" I hear the wheelchair pusher say. They disappear into the foyer. They're gone a long, long time. I sip my water. I finish my salad. I enjoy the time alone. I am thinking: "I can't keep doing this. I want to slip out. I do not want to be rude."

"People are strange," he says when he comes back. The man with the wheelchair kept asking him to open doors. It was very strange, he said. "He didn't really seem to be going anywhere."

One coffee lasted all winter, and how happy I was on the weekends, playing all that backgammon and keeping score and naming things funny names that meant something to us, skiing, then hunting morels and reading The Reivers aloud to each other every night.

It's very distracting, a loved person, and it makes the planet manageable. The planet, which is so large and lonely and blue, and also hurtling through dark empty space. All of which you can feel when you are alone.

I'm not un-whole. I'm not half a person. But being with someone is energizing and relaxing, the opposite of coffee. It organizes me. The doubleness amplifies things, but in a way called softening.

I love having a boyfriend. Men are not like cars or pets—the opposite. But having a man in one's life is like having a car in America—easier. A home without a man in it? It gets a little museum-ish. Not bad. Beautiful, and very very very still. Stewarded only by a woman, objects, life, can get weird to the touch, overly pristine.

Like most plans, the plan is pretend. I do not want a hundred cups of coffee, a hundred men. I do not want coffee. I do not want the wrong man. I do not want to be alone. I do not want to do this at all. Yesterday, I doubled down, one at lunch, one at 4 in the afternoon. Today I am sick in my bed, a summer cold, hell.

Especially good to do with someone one is sleeping with at night: the grocery store, swimming in open water (inside water better alone), dog-walking, talking about the friends, practicing foreign languages, thinking about houses, riding bikes, breakfast. Coffee in bed.

Sometimes I feel like a priest, hearing these men confess their lives and wives. Sometimes I feel like an officer of something, like the town of single people. Sometimes I feel like an ambulance chaser, gaping at their stories.

One day I get a trifecta of bad news—my family, my regular life, so many things can go horribly wrong. I call my ex-husband. My dear good friend. Dave and I are divorced, but we are terrible divorced people; we are friendly and helpful to each other and un-mad. We meet at the neighborhood bar, a place I can cry in if need be. Eight, nine years ago, I met this man, my ex-husband now, on Match. He wrote, "I do not know if I could keep up with you, but I know I would enjoy trying." He was the only person I went out with. He was the only person I married.

Then a woman comes in and I recognize her voice; she's a colleague, Joy. I haven't met her boyfriend, and I am happy to now. I introduce my ex, Dave. I happen to know she met her boyfriend on Match. This was years ago. They settle in next to me, happily, and order four appetizers and begin playing the game at the bar, little cards with embarrassing questions.

Then my friend Ellen comes in. With her online boyfriend in tow. We hug and carry on. Introductions all around. We sit at the bar facing forward and drink our drinks, man woman, woman man, man woman. I whisper to Dave, "Everyone at this bar met online. Match." He gives me a shocked look. I finish my martini.

Once, I told someone I was the first Match divorce. They were stunned and curious. I was just kidding. I'm sure there were others, before me.

Back then, you posted one photo. It scrolled down so slowly, like a creaky roller blind. He was the first person who wrote me. I wrote him back before his photo finished unrolling. I wrote him back while his forehead was still arriving. He was great right away.

I don't think we look or don't look for love; the heart is a receptor, always working. In spite of our best efforts to protect or hide it. Love looks for us, regardless of how we orient ourselves.

All the coffees have pulled me into human presence, out of myself. The coffees are like Empathy Boot Camp. The coffees remind me of short stories I can't stop thinking about. I have heard 41 stories of actual lives: lives bungled, misrepresented, frayed, lit by moments of luck or beauty. Lives a lot like my own life. Raw like this, pitched toward me, hope unclenched. I've mostly wanted to run away. I do not even drink coffee. I drink water.

So I am moving through these coffee shops, Leaf and Bean, Beaners, Cuppe Diem, carefully, a strong, clear woman, cool water. I can't help listening to each man with my heart. Sometimes I think men mistake women for nature. But with each sip, I'm closer, I know I am closer, to finding the place in me where love given comes from. And how it is.

Sweet little mysterious sip by sip...  

More dating adventures: What another woman learned from her 100 dates


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