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“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.”

I asked them what women should give up if they want to find a good mate.

“I don’t know that you’d have to give up anything—don’t start off with the negative!” Diane said. “Women today start off with that mind-set—they have a long list of what they want and think they have to cross things off of it. Why not just look for someone you enjoy being with and see where it goes? Start off from a place of optimism instead of what the guy might be lacking.”

Kathryn agreed. “I have a very dear friend who has single girls,” she said. “I wanted one of them to meet a young attorney who’s smart and funny and donates time to kids. She Googled him, found a photo, and said he wasn’t good-looking enough. She wouldn’t even meet him. Girls today are stopping relationships from happening before they even have an opportunity to develop. There’s a romanticized expectation of being swept off your feet from the get-go and sustaining that level of excitement, but the way love happens is over time.”

That’s how it happened for Connie. “I didn’t even like my husband when I met him,” she said. “I was working in fashion and he was schlubby. He was sort of an oddball. He asked me out and I didn’t want to go out with him. But he was persistent and as I got to know him, he not only turned out to be a wonderful guy, but he turned out to be the love of my life.”

The more I spoke to people about relationships—younger single women, older single women, married women, single men, married men, and women from my mother’s generation—the more I found myself asking the same questions: How did the search for love get so confusing, and was this modern way of dating making women happy?

2 The Romantic Comedy That Predicted My Future

I was 20 years old when I first saw the movie Broadcast News, but little did I know that it would predict my future. Holly Hunter plays Jane, a single network news producer whose best friend is her talented and witty colleague Aaron, played by Albert Brooks. They talk on the phone late at night, finish each other’s sentences, laugh at the same things, and understand each other the way nobody else does. Aaron, who is smart, funny, and kind, is in love with Jane, but Jane falls for Tom, the handsome but shallow newscaster played by William Hurt. Tom, who’s all about style over substance, stands for everything Jane rails against. Jane is drawn to him anyway. In the end, she realizes that she can’t compromise her values enough to be with Tom—nor can she compromise enough to be with Aaron. She loves Aaron deeply, but she doesn’t feel any fireworks.

We’ve all been there, haven’t we?

Jane’s dilemma—the choice between fireworks and friendship— may seem age-old, but it’s not. The internal struggle might be, but the freedom for women to choose not just one or the other, but neither, is relatively new. Instead of picking Aaron or Tom, Jane decides to wait for Mr. Right, who, incidentally, never shows up. At the end of the movie, when we see these characters seven years later, Jane vaguely mentions that she’s dating a guy, but so what? What are the odds that this relationship will work out, given that she’s probably been in several relationships in the past seven years that seemed promising but didn’t pan out? Besides, who’s to say that this guy is better-suited for her than Aaron, her emotional and intellectual soul mate? Meanwhile, we learn that Aaron is married with a son, and Tom is engaged.

It’s a sad ending, but when I was 20, I didn’t question whether Jane had made the right decision. That Jane ended up unmarried and childless, well, I chalked that up to—get this—the filmmaker’s misogyny! I’m not kidding. I’m completely embarrassed by this now, but I actually had conversations with female friends about how Hollywood wasn’t ready to show a strong woman standing her ground without somehow punishing her for it. It never occurred to us that this was simply a likely outcome to Jane’s choice. In fact, many of us went through our twenties and thirties making that very same choice—Prince Charming or nobody!—and ending up single.

What my friends and I called “misogyny” turned out to be “reality.”

It wasn’t until I watched the DVD in my late thirties that I realized I’d become Jane, passing up the Aarons of the world only to appreciate too late that what I want most in a partner is an Aaron. But like Aaron in the film, those guys my friends and I passed up earlier had gotten married.

At 20, I remember thinking that the saddest moment in the film was when Aaron confesses to Jane, “And I’m in love with you. How do you like that? I buried the lead.” My heart broke for Aaron.

Two decades later, the saddest moment for me was when a heartbroken Aaron predicts the consequences of Jane’s rejecting him for the charming but shallow Tom: “Six years from now, I’ll be back here with my wife and two kids. And I’ll see you, and one of my kids will say, ‘Daddy, who is that?’ And I’ll say, ‘It’s not nice to point at single fat women.’ “ Now my heart broke for Jane. I knew how truthful Aaron’s cutting remark could be.

A BETTER-LOOKING BILLY CRYSTAL

A couple of years after Broadcast News came out, When Harry Met Sally hit theaters. This time, best friends do fall in love. There was something incredibly romantic about the idea of, Hey, wait a minute, take a second look at the guy who’s your buddy. But still, back in my twenties, I wasn’t interested in the Billy Crystals of my world. Again, stupidly, my friends and I considered this message insulting. Why should someone like Meg Ryan lower her standards? In real life, we asked, would someone as beautiful as Sally go for someone like Harry? Probably not. He’d have a crush on her, and she’d say she just wants to be friends.

But in our “real-life” scenario, we didn’t think through what might happen next: She’d reject him and date more attractive men, while he’d go off and marry someone else. Maybe she’d find someone, but maybe she wouldn’t. Or maybe she would, but not someone she connects with as strongly as Harry, or not in time to have the children she wants.

I had no sense of this when I was 22 years old and watched Sally sob to Harry, after she learns that her ex-boyfriend is getting married, “I’m going to be forty!” Harry reminds her that she’s only 32 years old and that 40 is eight years away, but Sally cries: “But it’s there, it’s just sitting there like a big dead end. It’s not the same for men. Charlie Chaplin had babies when he was seventy-three.”

At the time, the idea of being 40, much less 32, seemed eons away to me. I took it for granted that I’d be married by then. I never thought my life would be like Jane’s at the end of Broadcast News; I thought my life would be more like Sally’s, a wonderfully romantic story of best friends who fall in love, except it would happen at age 30, and I’d be married to a man I considered to be not just my best friend, but also incredibly sexy—a better-looking Billy Crystal, a smoother Albert Brooks. Quite an assumption, given that I look nothing like Meg Ryan and, on a good day, have maybe half the charm of Holly Hunter. But like many young women, I identified with Meg and Holly. Delusional as it sounds, when I was dating in my twenties, I thought my romantic prospects should be on par with theirs.

And so did many of my friends. Sure, we would have denied it, but we would have been lying. We said we didn’t believe in the fairy tale, but when push came to shove, we wouldn’t settle for less than the fairy tale, either. We said we wanted true love, but we sought out romance and confused it with love. We knew that movies were fiction, but on some unconscious level, we watched them as if they were documentaries.

As Allison, a single 38-year-old in Minneapolis wrote to me, “At twenty-seven, when I got into an argument with my boyfriend—who I loved—I was looking for the romantic comedy response. My mistake.” They broke up, and she regrets that decision. Now with no romantic prospects on deck, she was planning to get inseminated to become a mom on her own.

BRIDEZILLA

It’s not just movies, of course. There’s an entire industry devoted to fairy-tale weddings (which, incidentally, became a source of conflict in the hugely popular Sex and the City movie), and even the newspaper announcements themselves, with their over-the-top “we looked across the room and our eyes met instantly” stories, fuel the fantasy of what love is supposed to look like when we find it. But just as in the movies, these newspaper accounts—the so-called sports pages for women—never tell you what happens in the actual marriage.

Elisa Albert, whose own wedding was featured in The New York Times, knows this all too well. As she put it: “My Times wedding announcement read, as so many do, like a smug sigh of relief.” What followed, though, was a train wreck of a relationship. She was separated within a year, and divorced shortly thereafter.

In her essay in The Modern Jewish Girl’s Guide to Guilt, Albert describes her whirlwind romance leading up to the Times announcement, the fabulous and moving wedding ceremony, and the post-wedding reality that set in as she and her husband realized they were—and always had been—incompatible when it came to marriage. Just as it might be helpful if movies made sequels showing the couples’ marriages, Albert wishes that wedding columns would print “divorce announcements” as follow-ups to all the enviable romantic courtship stories. At least then, she believes, single people would have a better idea of what love is and isn’t.

She has a point. I went through my twenties and thirties saying that I wanted true love, but how could I even know what that was? Married people rarely talk about the reality of their marriages with their single friends, and the only “love” stories most of us see onscreen are the kind where once a couple finally kisses after working out their conflict, it’s like a collective orgasm for the audience. After that, our interest in them deflates. The story’s over. We’re left to assume that these couples go on to happily ever after, but if the couple had so much trouble simply getting together, what makes us think they’ll have more success in holding a marriage together?

You’re probably wondering why any of this matters in a book about finding the right guy. You’re probably wondering why I think anyone with half a brain is going to be influenced in their dating lives by movies or TV shows or romance novels or wedding announcements or the covers of People magazine. If you’d asked me years ago whether I thought this stuff influenced me, I would have rolled my eyes. I mean, we all know that even leading men don’t meet the leading man ideal in real life. (Remember Hugh Grant cheating on Elizabeth Hurley with a prostitute? How about Brad Pitt leaving Jennifer Aniston for his costar?) But then why do many of us overlook men who don’t fit a fantasy man ideal but who would make wonderful life partners?

I thought about what the late psychologists Willard and Marguerite Beecher wrote about what they called “the infantile attitude toward marriage” in their book Beyond Success and Failure: Ways to Self-Reliance and Maturity: “We can only guess at the extent of it when we realize the number of love stories that are ground out and consumed each month for books, periodicals, TV, radio, movies, and the like. People would not buy such stuff if they did not believe in its probability. We find no such sale for fairy stories, which are no more fantastic.”

THE NON-PROBLEM PROBLEM

These days, in the movies or in real life, there’s not a lot of external conflict to overcome in order for two people to get together. It’s less about class or religion or geography or valid value differences than it is about the inner conflict of not knowing whether this person is The One.

In other words, nowadays you don’t fall in love with Romeo and say that the relationship is doomed because he’s a Montague. Instead, you start dating Romeo and overlook the fact that he’s a Montague, but the second he spends too much time playing video games, or he forgets the name of your best friend from high school, you wonder if you should try to find someone more mature or attentive. Instead of falling for a guy and discovering a seemingly insurmountable practical obstacle (like, there will be a civil war if you get together), we fall for a guy and then create our own seemingly insurmountable obstacles as to why we can’t be with him (isn’t funny enough, has a tendency to get stressed out during tax season). It used to be that lovers knew they wanted to be together but couldn’t. Now it’s that lovers can be together but aren’t sure they want to. And then we complain that we can’t find a suitable spouse.

I was starting to realize that despite everything I believed on an intellectual level—despite the strong, sensible person I thought I was—deep down, I had a classic Cinderella complex. I expected that, as the famous song goes, someday my prince would come and “thrill me for ever more.” It never occurred to me to trade those impractical glass slippers for shoes I could actually wear.

A SOLE SOUL MATE

When I look back on the way I dated in my twenties and early thirties, it’s not surprising that I thought it was perfectly reasonable to stay single while holding out for my ideal man. After all, everyone else seemed to be doing that—in real life and every time I clicked the remote control. During my peak dating years, prime-time TV was packed with series featuring sexy, successful single women looking for love, surrounded by surrogate families of wise-cracking, lovelorn singles like themselves. Two notable exceptions were Everybody Loves Raymond, a show about a marriage that, ironically, seemed to be of little interest to young single women aspiring to marriage, and Mad About You, a hip, smart comedy about a young couple adjusting to married life, which did appeal to young single women until a baby was added to the show, at which point viewers stopped watching and the show went off the air. Was this perhaps too much reality for single women dreaming about happily ever after?

On the single gal shows—Ally McBeal, Caroline in the City, Friends, Sex and the City, Grey’s Anatomy—viewers would tune in to watch a woman date a guy, only to talk endlessly with her girlfriends about why he’s not right for her, and why maybe she should look for someone better. There was always the assumption that she’d end up with her “true love” in the end—that there was a single soul mate and therefore a clear right choice when it came to a partner. These characters worried about making a mistake because there seemed to be only one chance at getting right, so they’d better be darn sure this guy was it. Nobody seemed to be saying there might be lots of “right” guys. In real life, of course, each partner has his pleasures and his drawbacks, but we rarely see real life played out onscreen.