So I had a choice: I could either rail at the plight of the single female looking for love, or I could use this information to my advantage. As Greenwald told me, there was some good news: I had a chance to make a fresh start and get it right this time by dating guys with qualities that might actually make me happy in the long run.
The long run seemed to be Greenwald’s focus. Over the past decade, she’d had a hand in several hundred marriages. And while many of these women initially resisted casting a wider net and focusing on subjective criteria, none of their marriages, to her knowledge, has ended in divorce.
So maybe she was on to something.
HAPPY WITH MR. NORMAL
When happily married women told me what they thought was important as you get older, similar themes emerged: What matters is finding the perfect partner—not the perfect person. It’s not about lowering your standards—it’s about maturing and having reasonable expectations. There’s a difference between what makes for a good boyfriend and what makes for a good husband. Over the years, stability and dependability outrank fireworks and witty banter.
My college friend Amanda, who is 39 and has been married for twelve years, told me that she remembers the pressure that came from society in general—and her social circle specifically—in terms of the kind of guy she should be dating.
“I remember in graduate school, this female professor, who was single and miserable, heard that I was dating Barry, and commented to a mutual friend that I could ‘do better.’ I remember thinking that she had no clue, and that no one could hope for a smarter, nicer, more promising person. History has proven me right. Barry may not always dress the way I like, or do Mr. Fix-It jobs around the house instead of watching football, but he’ll do anything for me. He makes me chicken soup from scratch when I get the flu, and he makes it without any salt to watch out for my blood pressure. In the end, that’s love and that’s a great marriage.”
Amanda said the biggest misconceptions she had when she was single were that consistency equals boring and that compromise is a negative word. She hopes her daughter has her priorities straight when she starts dating one day. “I couldn’t have married Barry—or anyone else, for that matter—if I’d nitpicked over the things I see single women rejecting guys over now,” she said.
Elise, who has been married for eight years and has two children, described her relationship with her husband this way: “When I turned thirty-five, I had just been dumped by this guy who had the qualities I thought I wanted, and I was devastated. A few months later, I met my now-husband, who possessed only a few of those qualities. The sparks didn’t fly immediately. Instead, he has other qualities I really wanted: complete integrity, total honesty, willingness to do the right thing even if it was difficult, stability and, most important, love and understanding of me. The reason I hadn’t met Mr. Right yet was because I was wrong about the qualities Mr. Right should have!”
Suzanne would agree. A 30-year-old marketing executive who lives in Austin, she told me that she married the guy who seemed like Mr. Right the first time, but is now married to the real Mr. Right. She laughs when she thinks about the mistakes she made in picking her first husband—and almost the second.
“For me,” she explained, “zeroing in on the nonnegotiables while being able to forgo the whipped cream was the real key.” After passing up a third date with an interesting guy because he wore sandals and had a cat, she told me, “I became ‘enlightened,’ which basically means that I was willing to overlook the stupid stuff. And now here I am, with the guy I want to grow old with.”
Of course, almost everyone out there dating knows that what Greenwald called the subjective traits are important. It’s just that we often place the same value on the objective traits and the subjective ones, and it’s hard to find a real live human being who has equal measures of both. If a guy has more subjective traits than objective traits, we rule him out. But if he has the objective traits, it’s harder to rule him out because objective traits are easier to measure, and we assume the harder-to-see-on-the-surface subjective ones are there, but just aren’t as apparent. Obviously, this isn’t always true.
Lynn, who is 42 and divorced, certainly looks at things differently now. “I had the handsome, square-jawed husband,” she explained. “And when he cheated on me for the third time, and we got a divorce, I started to learn that the superficial does not matter in the long run. What matters is finding a person of substance. Unfortunately, some of us don’t realize that until we’re in the been-there, done-that category.”
Lynn told me about two great guys in her office who have had a really hard time dating. One of them, Brad, is stocky and balding but, she said, “when you get to know him, you find he is witty, honorable, hilarious, intelligent, and downright adorable.” A lot of women didn’t look past the bald head and less-than-perfect body, and it wasn’t until last month, when Brad turned 38, that he got married.
“A man doesn’t have to look like a Ken doll to be a keeper,” she said. “My friend Brad sure is, and the girl who has kept him is a lucky woman.”
Lynn has another colleague, Mitch, who is 30 years old and is one of the nicest men Lynn has ever known. He’s shy, Lynn said, but when you get to know him, he’s a lot of fun to spend time with.
“He doesn’t have a super-trendy hairstyle,” she said. “He’s not a bad-looking guy—he’s just an average-looking guy. He has so many great qualities, but it seems to me that women in his age group don’t even look at him. It makes me sad. From my perspective, at forty-two, I know that there are many younger guys out there who really want to find love, who want a commitment, who want to be married, who want kids. And they’re often overlooked by women ages twenty-five to thirty-five who want to have it all.”
SOMEONE TO KNOCK SOME SENSE INTO ME
I knew that Rachel Greenwald was right—I needed to approach dating differently. But even if I tried looking for those more subjective qualities, I still had a problem: I wasn’t meeting any men.
I thought I should call a matchmaker.
For me, this seemed like a radical step. It never occurred to me to hire a matchmaker when I was younger because I always believed I’d meet a man on my own. He’d be sitting next to me on an airplane, waiting in line behind me at the dry cleaner, working in the same office, attending the same party, hanging out at the same coffeehouse.
It seemed ridiculous now, when I thought about the odds of this happening. After all, we don’t subject other important aspects of our lives to pure chance. When you want to get a job, you don’t just hang out in the lobbies of office buildings, hoping an employer will strike up a conversation with you. When you want to buy a house, you don’t walk aimlessly from neighborhood to neighborhood on your own, hoping to spot a house that happens to be for sale, matches your personal taste, and contains the appropriate number of bedrooms and bathrooms. That’s too random. If that’s your only method of house hunting, you might end up homeless. So you hire a real estate broker to show you potential homes that meet your needs. By the same token, why not hire a matchmaker to show you potential partners?
The idea of looking across the room and locking eyes with a stranger still seemed more appealing, but in what room, exactly, would I find this charming stranger: in my office, which consisted of me and only me? In my living room or kitchen, where I went when I wasn’t in my office? At a bar, which wasn’t exactly a mecca of quality men?
Single women I spoke to complained of the same problem: Where in the heck would a modern busy woman magically “run into” The One? During the week, many single women have a schedule like this: Wake up, commute to work, work all day, stop at the gym or your all-female book club, microwave your dinner, watch a little TV, reply to e-mails, and go to bed. And the weekends? Have lunch with girlfriends, run all the errands you didn’t have time for during the week, pay bills, open mail, work out, and spend another Saturday night at a party or trendy bar hoping
to lock eyes with that handsome stranger across the room. I’m not saying it can’t happen. I’ve actually dated a couple of those handsome strangers, but I never ended up marrying them. So I didn’t want to leave things up to Fate or Destiny anymore.
I wanted a matchmaker’s help, but I didn’t want her to dismiss my objective criteria completely—I just wanted someone to add some perspective and common sense to my search in the way Greenwald was suggesting. I wanted someone who could say, “You know, he may not seem like your type, but trust me on this one.” I wanted her to remind me of what’s important, and help me break my pattern of ruling out good guys for all the wrong reasons.
So I got on the phone and called up Wendy, a local matchmaker I knew about, and we arranged to meet for coffee. A week later, over steaming cups of latte, I gave her the rundown of my dating casualties: the musician I lived with in my twenties (cute, smart, and creative, but the theory that opposite personalities attract didn’t seem to work for us after we moved in together); the lawyer who came next (cute, smart, funny, and successful, but he became so possessive that even my most open-minded friends thought he was creepy); the brilliant entrepreneur (cute, funny, and successful but maddeningly unreliable and egotistical); the TV writer who wasn’t ready for a prime-time relationship (cute, smart, funny, and creative but not interested in committing to me); the charming investment banker who picked me up at a party where, I later learned, he was supposed to be someone else’s date (that should have been a red flag, right?); the journalist who lived far away (cute, smart, funny, creative, and the nicest guy on the planet, but we could never agree on where to live and the kind of family life we wanted); the political consultant I shared a lot of interests with, and who seemed to be great most of the time, except when he was being dishonest or went off his antidepressant and anti-anxiety medications (cute, smart, and talented, with a Jekyll and Hyde personality); the sexy film-maker from Match (smart, funny, and successful, but not good dad material).
All of these guys were initially attractive on paper, I told her, but clearly, I had a pattern of making the wrong choices. Did she think she could help?
Wendy thought she could. In fact, she already had someone in mind.
6
$3,500 for Love
I’m not proud of this, but I almost rejected the first guy Wendy sent me. Mind you, I hadn’t even met the guy. I hadn’t seen his picture yet. And, in fact, from what Wendy had told me, he sounded a lot like the kind of person I was looking for. He was four years older than me (unlike those speed dating guys in their fifties). He’d been married before (and wanted to be married again). He was a father (and loved kids). He was highly educated (but down to earth). He collected first-edition books (and read them). He was financially stable (and liked his work).
Even so, when I heard that (1) a year earlier, he’d been distraught about his divorce (lately I’d gone out with a string of guys who spent the whole time recapping the collapse of their marriages); (2) he had four kids (“If we got together, there would be five kids in our family,” I told Wendy. “That’s not a family, that’s a litter!”); (3) he was an avid sports fan (a turn-off to me); and (4) he grew up in a place that I associated with beer-can-smashing guys with thick accents, while my “type” was sophisticated intellectuals—I wanted to see who else she had for me.
She listened to my concerns, but asked me to reconsider. A few days went by as we went back and forth on e-mail. She assured me that this guy was far from “the belching, rough-talkin’ Bronx-born sports nut,” but was instead “Ivy league-educated and corporate-lawyer refined.” In response to my questions about his hairline, stature, and wit, she replied that he had “height, hair, and humor.”
Wendy didn’t mince words. “We simply cannot nitpick people to death (he can be from Manhattan, but not the Bronx; he can have two kids but not four; he can like sports but not too much).” She wrote that my overly analytic mind “runs the risk of precision-thinking yourself out of a human connection!”
I trusted Wendy. She wasn’t the pushy, used-car-salesman breed of matchmaker, out to take my money and send me a match that took the least amount of time and effort on her part to find. She wasn’t an impersonal corporate entity that signs up anyone who comes along instead of hand-picking men from the community. Nor was she the stereotypical and much-lampooned middle-aged woman in a muumuu who reads your aura and claims to have a “sixth sense” about people.
She was a sharp, hip, happily married thirty-something mom who’d had remarkable success setting up friends, and had become, by accident, a local matchmaker. She didn’t advertise. She only took clients referred by people she knew. She had facilitated six marriages in the last few years, with another couple recently engaged. And she thought this guy and I would really like each other.
Finally, I agreed to meet her match.
“Accentuate the positive,” she wrote, and sent me his name so I could expect his call.
That’s when I realized how far off the deep end I’d gone: I was disappointed by his name. I know this sounds nuts, but it was a name you’d give to the nerdy sidekick in a movie, a name that would get a kid teased on the playground. It was like that scene in When Harry Met Sally when Sally insists that she had great sex with a guy named Sheldon, and Harry replies, “Sheldon? No, I’m sorry. You didn’t have great sex with Sheldon. A Sheldon can do your taxes. If you need a root canal, he’s your man. But between the sheets is not Sheldon’s strong suit.”
So much for being open-minded. Not only had I microanalyzed this guy’s background, but I’d judged something as irrelevant as his name! And it gets worse: I took that nerdy name, typed it into Google, found a photo online, and thought, “Hmm, his face looks heavy.”
Let’s review here: The guy, whom I’ll now call “Sheldon,” sounded interesting: smart, funny, accomplished, kind, loves kids, wants a serious relationship—and I was spending time analyzing his name and whether he might lose twenty pounds. Thankfully, I came to my senses and said nothing to Wendy. By bedtime, I realized he was the most interesting potential date I’d been set up with in a long time, and I felt genuinely excited to meet him. I eagerly awaited his call, which came the next day, when I was out. He left a nice message. I called him back and left a message. Then it was the weekend and I didn’t hear from him again.
On Tuesday, Wendy had some bad news. Sheldon had called her Monday night. Apparently, in my six days of ambivalence about meeting him, he’d gone on a few dates with someone else (not through the matchmaker), and by the weekend things had intensified and now they were physically involved. He wanted to know where his budding relationship might go before he called someone new. Sheldon was no longer available.
Great.
When I told female friends this story, they couldn’t understand it. “Wait, he just met this woman,” one friend said. “Why can’t he meet you, too?”
“That’s an idiotic dating strategy,” said another. “He’s known her a week. How does he know he wouldn’t like you better?”
I tried to feel reassured by my friends’ comments, but instead they made me respect Sheldon more: the thought of “better” didn’t seem to occur to him. He had no so-called dating strategy. He was an ethical guy who didn’t sleep with one woman and go on a blind date with another. Sheldon’s approach was so much saner. The woman dating Sheldon probably didn’t overanalyze things to death like me, either. I doubted she was obsessing over whether he’s too into sports or needs to lose a few pounds or is slightly nerdy or has too many kids.
Women like me, those who are perpetually single, often do. Relationships are like a game of musical chairs—if you wait too long to take a seat, all the chairs will be taken.
And that’s pretty much what happened. Wendy tried to find me someone new, but a 41-year-old single mom isn’t an easy match. Weeks went by as she explored the possibility of setting me up with a smart, funny, attractive district attorney
who was divorced with no kids, but the more she talked to him, the more she realized that he wouldn’t be flexible enough with dating around a child’s schedule; he simply had no idea what raising a child involved.
She asked if I would be open to other religions, and although I have a strong preference for someone Jewish, I found myself saying okay. But the more she talked to another potential match, the more she felt that religion would be an issue for him. She looked around for someone else, but there was nobody she knew in her small network in the forties-divorced-with-kids category who happened to be available and interested. She would have to go out and search.
When I think about that incident now, I’d like to believe that some of my initial nitpicking with Sheldon had to do with the fact that I’d paid $500 for two dates and, at $250 per date, with the financial stakes so high, it was reasonable to want to get the best two matches possible. But what did “best” mean? Wendy had no way of predicting chemistry between Sheldon and me, and he was, objectively, a match with good potential.
If I’m really honest, I think my reluctance to meet Sheldon actually had more to do with something I hadn’t yet admitted to myself: I still hadn’t come to terms with the realities of being single and never married at my age. I wasn’t ready, on some visceral level, to let go of the idea of being somebody’s first and only spouse, of being somebody’s The One and having the exclusivity of our own family unit.
I wanted a more conventional setup that didn’t involve thorny custody schedules, negotiations over where to spend the holidays, and issues with an ex-wife. But what age-appropriate single guy with no kids and no ex-wife was going to be interested in taking on a woman who was too old to have kids with him and whose time and energy was devoted mainly to her young child? It seemed that my most promising options were going to be divorced men with kids, and I was going to have to not just accept that, but embrace it.
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