The others nodded.

“I don’t know about you,” Olivia continued, half-joking, “but I would need to love someone very deeply in order to brush my teeth two feet away from where he’s taking a dump every morning.”

I suggested that, all kidding aside, bathroom doors can be closed, but opportunities to meet good men aren’t always open, and I asked the group how they defined settling. Did it mean picking a guy who’s truly annoying, or compromising on some desired qualities but getting other, more important ones? And what would those important ones be?

“Even if he’s nice and smart and attractive, I can’t be with someone boring,” said Nora, a radio producer.

“Exactly,” said Claire, a graduate student. “There are guys who are smart but then you’re shocked to learn that for all that intelligence, they’re just not that interesting. They have to be smart in an interesting way. They have to be curious.”

“Curious, but not earnest,” said Nina, a marketing executive. “They have to be a little edgy.”

“But not too edgy,” said Nora. “They have to be normal. But just not boring.”

I asked the women for examples of what they meant by boring.

“They have to have a sense of humor,” said Nina. “They can’t just be sitting there laughing at something funny I might say. Boring guys aren’t funny, but they think you’re funny.”

“Or the opposite,” said Claire. “They think that if a woman laughs at their jokes, she has a sense of humor. Only a boring person believes that.”

“Or a narcissist!” said Lauren, a fund-raiser for political causes.

“Well, narcissists are boring!” said Olivia, and the group broke into laughter.

I told these women—all reasonably attractive but not drop-dead gorgeous; all interesting but not off-the-charts fascinating—that at a certain point, they might get lonely going on all these dates looking for The Perfect One instead of building a nice life with Some One.

“I’m already lonely, but loneliness is better than boredom,” said Lauren. She’s finds her stable fund-raising job boring at times but it’s often fulfilling, too, so she won’t leave it for her true passion, painting, because it seems too risky.

“So you’ll compromise in your choice of a job but not your choice of a partner?” I asked. “You’re willing to spend eight hours a day in a good enough career instead of leaving it for your true love, being an artist?”

Lauren thought about this for a minute.

“Well, that’s different,” she said. “I’m practical about my career. But to be practical about love? You can’t be practical about a feeling. That seems so … unromantic.”

Just then, a cute-ish guy who seemed to be about thirty walked by and checked out the women. They ignored him. I asked why.

“Too short,” said Olivia, who is 5’2”.

“And what’s up with those glasses?” added Claire, who wears chunky glasses herself.

I wondered if they’d be open to dating a short guy with last year’s style of glasses if he had many of the other qualities they wanted: smart, funny, slightly edgy, kind, successful—and, of course, not boring. How much do first appearances matter?

“I’ve tried that,” Nora said, “but I can’t make myself become attracted to someone. You have to feel it from the beginning. If you aren’t physically attracted when you meet them, you’re always forcing it and it never works.”

At first I was surprised by how readily the twenty-somethings dismissed this cute guy without even considering starting up a conversation to learn more about him. I mean, this wasn’t college, where the playing field was pretty evenly matched in terms of available romantic prospects. This was the adult world, where people were pairing off and getting married, where the pool of single men was getting smaller, where there wasn’t a built-in mechanism for meeting like-minded people the way there’d been in the past.

But then I remembered myself in my twenties, when the possibilities still seemed tantalizingly endless—even if they weren’t.

DESPERATE BUT PICKY

Ah, the difference a decade makes. A few nights later, five single women in their late thirties to early forties met me at the same bar, where I asked the same question: Why is it so hard to find a good guy? I filled them in on the conversation I had with the younger women about boredom and loneliness.

“Check back with them in ten years,” Stephanie, an attractive 39-year-old pediatrician, said. “If they’re holding out for Prince Charming, they’ll be bored and lonely. The job won’t seem as exciting anymore, drinks with the girls will get old, and on holidays, they’ll be hanging out with their married friends and their kids, or their nieces and nephews, which will only make them depressed that they don’t have a family themselves.”

I admitted that I related to those younger women, who wanted to be in a relationship but had a very specific idea of what that guy would have to be like. And as I got older, I explained, my dating life slowly became this lethal paradox: desperate but picky. They knew exactly what I meant.

“That’s so true!” said Liz, a 37-year-old screenwriter. “I want to shake younger women and say, you know, the guy who laughs too loud in public may not love the way you chew raw carrots at dinner parties, but it’s not a deal-breaker for him.”

These women could easily list their former deal-breakers—the reasons they didn’t pursue relationships when they were younger. Here’s what they said:

• “He was very loving but he wasn’t romantic enough. On Valentine’s Day he made a mix tape of my favorite music and gave me an hour-long massage, but all day at work, whenever I saw the flower guy going up the hall delivering flowers to my colleagues, I kept thinking, where are my flowers? I wanted a guy who sent flowers.”

“He brought me flowers, but cheesy ones that just spoke to bad taste—and the sense that I wasn’t worth something more thoughtful.”

“He wasn’t exciting enough. I felt like we were already married, which was nice in a way, but this was supposed to be the courting period.”

“He had long nose hairs and they grossed me out, but I didn’t have the courage to ask him to trim them, so I stopped seeing him.”

“He cried. The first time, I wasn’t thrilled, but okay. The second time, I bailed. I felt he was too weak for me.”

“He was too predictable. Then I started dating guys who always kept me on edge and I never knew what to expect. It was terrible. Now I’d give anything for predictable.”

“I was embarrassed by his voice. Sometimes when he’d answer the phone at my place, people would think he was me, because I have kind of a low voice. But otherwise, he was very masculine. And a great guy.”

“He was too optimistic. He was so cheery all the time, even early in the morning when the alarm went off, and I found that grating. He always found a silver lining—‘The stove broke, let’s go out to dinner!’—but I’d be upset that I had to buy a new stove. I didn’t want to ‘look on the bright side’ all the time. Then I dated a guy who was more cynical and after a while, it depressed me. So I tried to get the optimistic guy back, but he told me I was too pessimistic!”

“He was completely bald except for one of those rings of hair around his head and a little tuft poking up in the front. It was such a turnoff, but I tried to get over it because I really, really liked him. My friends said, ‘He has a nice face, he has a nice body, and besides, most guys lose their hair eventually.’ But he was only thirty-five. I’d always been attracted to guys who had the kind of hair you could run your fingers through. Now I’m lucky if the guys I meet have any hair at all.”

“He thought it was funny to make up strange words, like ‘fabulosa.’ He did this a lot—and in public, too. Once he said to someone at a party, ‘Being a doctor isn’t just one fabulosa after another’ and I was so embarrassed. I broke up with him the next day.”

“He loved me too much. I felt like he was too much of a puppy dog, always looking at me with those adoring eyes. I wanted more of a manly man.”

“He wasn’t refined enough. He couldn’t order off a wine list. He’d never seen Casablanca. I wondered, how can you be thirty-two years old and not have seen that?”

“I just wasn’t feeling it—and now I think, what was I supposed to be feeling? Because, actually, I liked being with him more than any of the guys I felt strong chemistry with before or since.”

Listening to these women, I thought about the reasons I’d passed up guys when I was younger, often sight unseen. One of the most memorable is Tom, a client of my lesbian hairdresser. She’d told me he was a handsome, charming, brilliant chemist and wanted to set us up on a blind date.

“He’s the only guy who does it for me,” she said, which sounded like quite an endorsement. Add the fact that I have a science background, and this guy seemed incredibly hot. But I said no, back when I was 29, because when my hairdresser said that Tom had red hair, I didn’t think I’d be attracted to him. I just knew that red hair wasn’t going to work for me. (Apparently, my bar for men was higher than that of a lesbian.)

There was also the cute, smart, funny lawyer I went on several dates with until I lost interest because he overused the word “awesome.” I remember telling a friend, “Everything is ‘awesome’ with him. It’s not ‘great’ or ‘wonderful’ or ‘interesting’ or even ‘cool.’ It’s always ‘awesome.’” I tried to get past it, but it irritated me every time he said it. (Somehow, the fact that I said “like” and “you know” all the time didn’t seem to irritate him.)

In my early thirties there was the adorable software developer I met at a party who gave me his work number and told me to call there anytime because, he said, “That’s where I always am.” I didn’t want to be with a workaholic, so I never called. It didn’t occur to me that maybe he was at work all the time because he was starting his own firm, or that if he had a girlfriend, he might have more of a reason to leave at night. Nor did I bother to find out, because I always assumed there would be another setup, another guy at a party, or another online prospect. And even when the available guys and the opportunities to meet them seemed scarcer as I edged into my mid-thirties, I only got into serious relationships with men who met my rather strict and, in hindsight, superficial criteria. I had the attitude of, “I didn’t wait this long searching for The One, only to end up settling.” But would I really have been settling with the red-headed chemist, the lawyer who liked the word “awesome,” or the software guy who happened to work until midnight as he launched his business?

I’ll never know.

Like me, the women I met with at the bar were embarrassed by the way they’d dismissed men in the past, evaluating every guy as either too-something or not-something-enough. These guys didn’t fit our image of the person we thought we’d end up with, leaving us to end up with nobody.

I asked the group if these types of things would still be deal-breakers for them now.

“If I met a guy now who hadn’t seen Casablanca,” said Kathy, a 38-year-old consultant, “I wouldn’t rule him out, but I would still be aware of it in the back of my mind. I can’t say I’d dismiss it completely because it speaks to a larger issue of cultural void. Overall, though, my deal-breakers have changed.”

What would be their deal-breakers now? Someone with an addiction, someone who had a bad temper, someone who’s unkind, someone who doesn’t have a job, someone who’s not warm or doesn’t have a generous spirit, someone who’s inflexible, someone who’s irresponsible, someone who’s dishonest, someone who wouldn’t be a great father, someone who’s old enough to be their own father. The rest, these women feel, is negotiable, but it’s a realization that might have come too late: In their experience, the men who will date them now often come with these more serious deal-breakers, whereas the guys who would date them ten years ago didn’t.

“In a way, I’m still looking for the same kind of guys I was when I was twenty-five, except that I also want them to be family-oriented and be good providers, which I wasn’t thinking about back then,” said Beth, a 37-year-old pharmaceutical rep. “Those are the guys I used to break up with.”

Amy, a 43-year-old interior designer, agreed. She said that she always had boyfriends until she was 39, when, she explained, “I suddenly stopped getting asked out by anyone younger than fifty.”

So, I asked, why can’t they go back to those guys they’d passed up, who now sound pretty appealing?

In unison, they said, “They’re all married!”

WHO CARES IF HE’S SEEN CASABLANCA?

I had to wonder: Who were the women that married those guys? A week later, I met with some of them. On the surface, they seemed a lot like the women who’d dumped their husbands. They were around the same age, and similar in terms of looks and education. In fact, I could imagine these married women having become their single counterparts if it hadn’t been for one distinguishing quality: the ability to redefine romance. Nancy, who is married to the “predictable” guy, explained it like this:

“I think the difference between women who get married and women who don’t is that women who don’t get married never give up the idea that they’re going to marry Brad Pitt, and it never occurs to them that they might not get married at all. They may say, ‘I’m never going to meet anyone,’ but that’s just like saying, ‘Oh, I’m fat’ when you don’t believe you are. It’s something women just say, in a self-deprecating way. When you’re young you’re always meeting guys, so deep down you believe that The One will suddenly show up. It doesn’t occur to you that maybe it’s okay if The One doesn’t look like Brad Pitt and earn a gazillion dollars and make your knees go weak every time you’re together. Well, it occurred to me, but not until I was thirty-five.”

That’s when she met Mr. Predictable.

“So many women say they’d rather be alone than settle, but then they’re alone and miserable—and still holding out for the same unrealistic standards,” Nancy said. “They assume their soul mate will appear and it will have been worth the wait. Then they’re blindsided and shocked when that doesn’t happen. And it’s too late.”

Too late, she meant, for the life she has with the predictable guy.

“It is predictable,” Nancy admitted. “But it’s a lot better than always wondering what was going on with the more exciting guys. That wasn’t love. What I have now is love. I have an amazing husband and two wonderful kids. I couldn’t ask for a better family. And my husband is exciting, just in less obvious ways.”

Sara, who’s 42 and married to the ring-of-hair guy (who, at 43, is now completely bald, except he still has that tuft sticking out in front), told me that she feels lucky to have been at a place in her life at age 34 when she finally stopped getting hung up on things like how much hair a guy had.

“A year or two earlier, I wouldn’t even have considered meeting a bald guy,” she told me.

She’s glad she changed her mind, she said, because if she hadn’t, she would have missed out on falling in love with her husband—and probably ended up with no husband at all.

“I don’t know one available guy out there who’s as desirable as my husband and would also date me at this age,” she said. “If I were single today, my own husband probably wouldn’t date me either. I wouldn’t be on his radar. Why would a forty-three-year-old guy who’s kind and successful and funny date a forty-two-year-old woman when he could easily attract an equally interesting thirty-five-year-old who’s prettier and young enough to have kids with instead?”

I told Sara that a lot of women would be offended by that kind of thinking, but she just shrugged her shoulders.

“Let me put it this way,” she said. “It’s a good thing I met my husband when I did. Because if I’d passed him by, he’d be married, and I’d still be sitting around wondering where the few good men were.”

A FEW GOOD MEN

That’s exactly what I was wondering: Where were a few good men? When I sent out a mass e-mail looking for single men, ages 25 to 40, to interview for this book, a typical reply went like this: “I don’t know any single men, but do you need any single women? I know a lot of those.”

Two weeks later, I got a quorum—but only after I expanded my definition of “single” to include men who weren’t married but were in committed relationships. These guys, for their part, seemed as baffled as the women when I went back to the same bar and asked the familiar question: Why are women saying they can’t find a good guy?

David, a funny 29-year-old professor, thinks the problem is that good guys are out there, but women don’t recognize them as the good guys.

“A woman broke up with me because she didn’t like the clothes I wore,” he explained, “but she’s madly in love with a guy who dresses well but doesn’t call her.”

His 32-year-old colleague Dan laughed—he’d been there before. “Women never want what’s available,” he said. “If they can’t find the perfect guy at thirty, they move on to find something better. But they don’t learn from this. Even if they’re still alone five years later, they get pickier. Then they’re almost forty and they haven’t found the perfect guy, so they start to regret having broken up with us, but now we’re not interested in them anymore.”

Kurt, who’s 38 and engaged, said that’s exactly what happened with his exes. “And those perfect guys, if they do exist, want to date maybe the top one percent of thirty-year-old women. But every thirty-year-old woman I know thinks she’s in that top one percent. All women want a ten, but are they all tens?”

His question reminded me of something my married friend Julie once said: “The culture tells us to approach dating like shopping—but in shopping, no one points out the shopper’s own flaws.”

Steve, who’s 35 and dating a lawyer, feels the same way. “I think the reason some women have an inflated view of themselves is that in high school, they really did have the power, so they grow up thinking it will always be that way. And even in their twenties, they still do, to some extent, because they’re so in demand. A guy will spend all of his money courting her, investing in the relationship, and then one day she’ll suddenly say, ‘You know, you’re a great guy, but I’m just not feeling like this is what I want.’

“In their thirties,” he continued, “it’s the opposite. The girl gives the guy free sex, thinking she’s investing in the relationship that will lead to marriage, but then the guy, who is now the one in demand, suddenly says, ‘You know, I think you’re great, but you’re not who I want to marry.’ And the women are shocked, because guys used to worship them, but the balance of power has changed. And I can’t say I don’t feel slightly vindicated that those same women who rejected me five years ago now complain that they can’t find anyone.”

THE MARRIED MEN

Eric, a 38-year-old married writer friend of mine, is still friendly with the three girlfriends who broke up with him before he met his wife. He said he’s going to write a book one day about the way women analyze men.

“I’ve got two working titles,” he explained. “The first is My Wife Isn’t Perfect (But I Don’t Consider That Settling) and the second is I Have No Idea Why She Broke Up with Me (But I’m Married and She’s Still Single).”

Women, he said, might call ten of their friends and discuss, point by point, how a guy measures up on a whole host of attributes. Then, in the areas he falls short (he’s too messy, he’s not sensitive enough, he’s not making enough money), they think about whether they can “fix him” or “train him” to make him into what they want. Men, he believes, know that what you see is what you get—and accept it.

“When we decide to marry someone, we don’t think we’re going to fix our wives and we don’t try to change them,” he said. “We don’t get out the spreadsheet and break it down on a microscopic level the way women do. We either want to be with her, or we don’t.”

Another married friend, Henry, who’s 36, said that while some men are afraid of commitment, most aren’t. They want to get married as much as women do. Often, he said, it’s just a case of the guy not being into that woman, but also not wanting to give up the perks of the relationship.

“He knows he’s not going to marry her,” Henry said, “so he says, ‘I’m not looking for anything serious right now’ or ‘I’m not sure I want to have kids’ or ‘I’m focused on my career right now,’ which he thinks is telling her that if she wants this relationship to lead to marriage, she should look elsewhere. But women think the guy is confused and she can change him, when really the guy has made up his mind.

“Meanwhile,” Henry continued, “women can’t make up their minds. Every perceived flaw is dissected for months or years until a verdict comes down on whether they’ll marry him. Men know early on when they’ve met the person they want to marry. It’s a very visceral feeling. That’s why women are always flabbergasted when their ‘commitment-phobe’ boyfriend goes off and gets married a year later.”

For all their talk about romantic love, Henry said, women tend to analyze the situation too much. “They’re hypocritical,” he explained. “They say they want true love but you’d better be this tall and make this much money—and not have bad moods or be a real person, either.”

He’s probably right. Two months after my friend Julia broke up with her “uninspiring” boyfriend Greg, she started dating Adam, a sexy, ambitious surgeon. Adam was all the things that Greg, her nonprofit boyfriend, wasn’t. But the low-key, supportive nonprofit guy was all the things her new beau wasn’t. She was starting to miss Greg.

“I just don’t know which things I can live with,” she sighed, as she was about to fly to Hawaii for a romantic weekend with the surgeon.

But does it have to be this way? Isn’t there a middle ground between cold, hard analysis and intense passion?

WHAT SIXTY-SOMETHINGS SAY

When I asked half a dozen of my mother’s friends who had married in their twenties about this middle ground, they said the problem they’ve seen in their kids’ generation is that the middle ground doesn’t exist.

“I hear constantly from my daughter’s friends that they want men to have the same emotions they do, but men and women express emotion differently,” said Susan, who has two daughters in their thirties. “Young women expect men to be soft and caring and rich and gorgeous—they want everything.”

Connie shook her head. “You can wait for Prince Charming,” she said, “but even Prince Charming will have holes in his socks. You can marry the most perfect person in the world and you’ll still have problems to work through. But once young women see those holes, they’re no longer interested.”

“Our expectations were different,” said Melinda. “We expected to have disagreements. You didn’t go in thinking, ‘I’ll get married and if it doesn’t work out, we’ll get divorced.’ There’s a sense of being a team. You were committed to working it out. Today’s girls always think they’ll find something better.”

Of the group, none of the moms believed in the concept of your soul mate being the only person on the planet you were meant to be with. To them, a soul mate meant someone you have a deep connection with, someone who accepts you for who you are and vice versa, someone who is there for you at the end of the day.

“I think going through difficult times together makes you feel like soul mates,” said Kathryn. “Working through an illness, a financial issue, a parent’s death.”

“People don’t expect to work in relationships today,” June added. “There have been phases of our marriage when both of us needed things at the same time, and that could be very challenging. But I think a lot of women nowadays expect that they’ll always get every single one of their needs met and if they don’t, something’s wrong. Nothing’s wrong—that’s just the nature of two people being in a relationship.”

Mr Good Enough: The case for choosing a Real Man over holding out for Mr Perfect

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