The Don Juan of Our Time

A clever move? A foolproof line? a hidden power? For 25 years, the author has wanted to know how his high school classmate, David Spade, became the world’s greatest ladies’ man

Six times I tried to learn his secret. Sis different times I made a good hard run at it. The second time was at a restaurant in West Hollywood, a dark place, cave dark, his choice, A painful eye condition made him sensitive to light, so he kept himself cloistered much of the time in semidarkness—which only added to the aura I conferred on him and his secret, (Where better to meet a guru than in a cave?) As I entered the restaurant, a waiter stepped forward and asked if I was dining alone or meeting someone, I’m meeting David Spade, Oh? He seemed impressed, He led me to Spade’s regular booth, Moments later Spade appeared, I gazed into the darkness, able to discern only a few blond wisps jutting from a dirty brown ball cap and, under the drawbridge of his visor, his smiling blue eyes,

You haven’t changed a bit, I said.

You neither, he said.

We were both lying.

This was last year, when I was hoping to write a profile of Spade, the durable and popular comic actor, and more important, more germane, the greatest ladies’ man of all time. It was a task for which I felt uniquely qualified, because I’d known Spade long ago. We attended high school together in Scottsdale, Arizona. We graduated together in May 1982, and even back then, when we were pubescent boys, I knew Spade was the greatest ladies’ man of all time. He was voted Most Artistic, but the entire student body at Saguaro High School knew he was the campus Casanova, a walking stalk of catnip for every cheerleader and homecoming queen, i can still close my eyes and see Spade in a burst of vivid colors—royal blue Ocean Pacific shorts, black-and-white-checked Vans, beige puka shell necklace. I can see him flying across the gray quad on his skateboard, pirouetting around the caramel-legged girls in their short shorts and miniskirts, making them swoon and tee-bee and sigh his name.

I might be imagining the puka shells, but the rest is absolutely true.

Trudging to class in a chain gang of my fellow virgins, I often looked up and saw Spade striding before a troop of hot little desert Lolitas, each one presenting herself for his inspection. I once saw him make Tiffiny Lendrum (Best Dressed, Cheerleader) turn bright pink just by tossing a few wisecracks in her direction. At 16 years old I’d have traded half my life to make Tiffiny Lendrum turn bright pink. It was my lot, however, to tutor Tiffiny in English, while Spade taught her Advanced Spade-lish.

After graduation I continued to watch from afar as Spade cut a fearsome swath through society’s cheerleaders and homecoming queens—i.e., models and actresses. Now and then I would read in a magazine about his latest romantic conquest, and I’d turn to whoever happened to be sitting beside me at whichever bar. See this guy?, I’d say, flourishing the magazine. I went to high school with this guy, and this guy is the greatest ladies’ man of all time.

The response was always the same.

Get the fuck out.

Appearances can be deceiving, I’d say.

Sure, people would say, deceiving—but totally irrelevant? What’s his secret?

I don’t know, I’d say. No one knows.

Finally, two years ago, the world began to believe. Reports surfaced about Spade dating Heather Locklear, and the nation did a collective double take. Waves of shock were followed by indignant outcry. America, en masse, shrieked, “She’s dating him?” Late-night TV hosts took aim at Spade, skewering him with uncommon ferocity and thinly veiled jealousy. Spade was often a guest on those same shows, and while he tried gamely to plug his latest project, the hosts would invariably interrupt and grill him about Locklear. Bloggers—who treat everything good that happens to other people as a sign of the Apocalypse—treated “Spadelock” as a rain of frogs. She’s dating him? OMG! WTF? Some speculated that Locklear had been kidnapped, brainwashed. Others noted that she’d recently turned 40 and thus her eyesight was falling. Host threw up their hands and tossed Spade-Locklear into that anti-male catchall, “Unlikely Couples” with other Beauty-Beast duos like Paulina Porizkova and Ric Ocasek or Christie Brinkley and Billy Joel.

Only a few Spade bashers bothered to pull his file, his voluminous love dossier, which showed Locklear was no fluke. She was the latest name linked to Spade, the latest guest star in a long-running one-man show featuring Krista Allen, Julie Bowen, Lara Flynn Boyle, Sara Foster, Teri Hatcher, Gena Lee Nolin, Kristy Swanson, and many more. Spade was even said to have shared one of those girlfriends with George Clooney—and one report said the woman left Clooney for Spade. So often had Spade dated “out of his league” he was in a league of his own. Even his platonic girlfriends, Pamela Anderson and Courteney Cox Arquette, were among the most desired women on the planet.

Now I had Spade cornered, in his favorite restaurant, a shot of Jack Daniel’s at his elbow, and I had license, as a journalist, as a schoolmate, to ask him the obvious question. What’s your secret?

But first I decided to break the ice. You don’t just come right out and ask the king for the key to the castle. You don’t ask the master seducer for his secret without a little foreplay. I started with the standard reunion question: So, what have you been up to?

He grinned. After graduation, he said, the only thing he knew was that he wanted to be funny for a living. He’d tried college and found it wasn’t for him. So he hit the road, working seedy comedy clubs, earning $20 a set. “It was scary,” he said. “And lonely. Lonely is a word I never say, but it was a little lonely.”

Eventually Dennis Miller spotted him and introduced him to Saturday Night Live creator Lorne Michaels, who hired Spade as a writer. It was Spade’s big break, but in the short term it made his life that much lonelier. He was in over his head, working around the clock, sleeping at the NBC offices, getting nowhere. “I’m writing against Robert Smigel, Conan O’Brien, fricking Jack Handey. Forget about Hike Myers and Dana Carvey, Dennis Miller, Sandier, Farley, Phil Hartman. These are, like, the best guys in the world.”

Slowly he managed to squeeze his stuff onto the air, then push his way in front of the camera. He wrote his own breakout sketch, “Hollywood Minute,” the premise of which was nasty, brutish, and simple: Spade sitting at a desk, saying the meanest things he could think of about big stars. (Eddie Murphy still won’t speak to him.) “I’d take legs out,” Spade said. “I didn’t give a shit.”

Following his sixth season on SNL, Spade ventured out on his own. The moment felt right. He’d formed close friendships with the iconic comics of his generation, and several would soon become his collaborators. He and Chris Farley, in particular, had a special bond. They costarred in the much-loved buddy flick Tommy Boy and seemed like the second coming of Laurel and Hardy, or Aykroyd and Belushi, until Farley met the same fate as Belushi at the same age. In 1997, when he was 33, Farley died from an overdose of cocaine and morphine.

Spade couldn’t bring himself to attend the funeral. Farley, he reminded me, was actually the second best friend he’d lost. Not long after graduation our Saguaro classmate Bob Zwicky died in a car wreck. Zwicky was Spade’s shadow, his straight man. The two performed together at some of those seedy clubs.

There were other losses, Spade said. His father took off when he was a boy. His stepfather committed suicide. Hartman, his friend and mentor, was shot and killed. Lastly, in 2000, the strangest blow: Spade’s pal and personal assistant, David “Skippy” Malloy, attacked and beat Spade, stabbing him repeatedly with a stun gun. “It was way more brutal than we let on back then.” The walls and floors of his house, Spade said, were spattered with blood.

He saved himself by pulling a loaded shotgun from under his bed.

How did he come to have a loaded shotgun?

“Arizona, dude.”

To this day Spade doesn’t know the reason for the attack, and Malloy may not either. “He was coked up out of his mind.” Showing me the scars on his wrist and foot, Spade said the deeper scars are mental. He never sleeps or showers without the door bolted.

Our meal flew by, and when the waiter brought our check I realized that I hadn’t so much as broached Topic A. The secret. Still, I wasn’t worried. The plan was to hit a bar for a nightcap, and talking about women is always easier in a bar. Also, this being Hollywood, if the bar happened to be full of beautiful women, all the better. I could ask Spade about his secret while watching him put the secret to work.

But as we waited for the valet, Spade checked his BlackBerry and said something had come up. He needed to be somewhere else. Another time, he said.

Just then a woman strolled by, walking a small dog. She was clearly an actress or a model. Even the dog walked as if it did some modeling on the side. Spade looked the woman up and down. The woman looked Spade up and down. The dog looked Spade up and down. Oh boy, I thought, here it comes. Even the valet seemed taut with anticipation. But Spade let the woman pass without comment, returning his focus to his BlackBerry.

I felt horribly cheated, as if I’d come to see Cal Ripken—on the first day he ever pulled himself from the lineup.

Typically, at a dinner party or bachelor party, after I’ve delivered my standard sermon, “David Spade: Don Juan for a New Millennium,” someone will mention Warren Beatty. Or Derek Jeter. Or John Mayer. Or Josh Hartnett. To which I always say: Yes, yes, there are many legendary ladies’ men in Hollywood, and there always have been, going all the way back to Rudolph Valentino. Hollywood breeds and attracts ladies’ men in the same way a Wyoming trout stream breeds and attracts fly fishermen. Still, Spade is the greatest of all time, the king. In my power rankings I put him a notch or two above that remorseless Romeo, Justin Timberlake, whose paramours include Britney Spears as a virgin, Cameron Diaz in her prime, Scarlett Johansson before she channeled Tom Waits, and now Jessica Biel, who looks as if she subsists on a diet of honey, rose petals, and morning dew. Granted, Timberlake’s resume is formidable, but he and Spade can’t be compared straight up. A sliding scale is required. Sex isn’t baseball, it’s golf. Most men have a handicap—or believe they do, which amounts to the same thing—whereas Timberlake, or any other great ladies’ man you might name, has none. Timberlake possesses every gift the gods can bestow. Looks. Height. Hair. Brains. Brawn. Youth. Wealth. Talent. Take away these gifts and where would he be?

Spade City, that’s where. And Spade City is where the rest of us live.

Of course Spade possesses many of the aforementioned gifts, but since he also lacks many, he deserves more credit. Much more. Clearly he’s doing it with smoke and mirrors, trickery and guile, bubble gum and chicken wire. He’s the MacGyver of Macking. He knows some clever move that never fails, some foolproof line that’s been tested in the acid bath of singles bars, sorority houses, and nightclubs, some surefire attitude or approach or “Open Sesame” incantation that always, always works. He knows a story that makes hearts flutter, or else he knows which stories, which words, make a woman’s heart turn to stone. He must know something, because there’s no other logical explanation.

I don’t mean to suggest that Spade is bad-looking. His detractors do him a disservice, calling him scruffy, mangy, elfin. In fact he’s a perfectly decent-looking guy, with kind eyes and an easy smile, who takes huge glugs from the fountain of youth. He has the same mane of blond hair he had when we shared the stage in the Saguaro talent show, and he gets away with wearing the same kinds of surfer and skateboarder clothes. Also, he has genuine charm, and old-fashioned manners, and a voice that does whatever he wants it to. He can go deep or falsetto, redneck or effeminate, depending on his mood and the bit he’s doing. Even his normal speaking tone is effortlessly funny, because it contains an ever-present trace of snark. No matter what Spade says, it sounds as if it’s coming out of the side of his mouth, as if he’s goofing on you. But even more on himself.

None of which accounts for his astonishing prowess with women. There must be something more than meets the eye, something below the surface, some clandestine skill with which he compensates for the visible gap between himself and the Ideal—because isn’t compensation the name of the game? I have a friend who believes that when it comes to women, each half inch of hairline he loses means another compensatory $100,000 he must earn per year. In his heart my friend believes his math is as precise as it is pitiless. Spade and his secret are my friend’s last hope when that last half inch is gone.

There are books that speak to this sort of compensation. Terrible books. Dreadful books. Immensely popular books, all of which peddle the same warmed-over eyewash of mind control and manipulation. They read like the family Bibles of the Medicis and the Mansons, and they help no one. Certainly they contain no secret. It’s been my experience that if you want the secret, never go to the person who’s written a book about it. Go to the person who seldom discusses it.

To wit, Spade.

The third time I tried to learn his secret was in Las Vegas. He was doing stand-up at the Mirage, and he left a ticket for me. His set went over well. The crowd responded not only with enthusiasm but also with warmth, as if Spade were an old friend. A guy behind me yelled out “Joe Dirt!” As much as Saturday Night Live, as much as the long-running NBC sitcom Just shoot Me, as much as his current CBS sitcom, Rules of Engagement, Spade is known and recognized for that cult favorite, Joe Dirt, the story of a white-trash Odysseus with a bad mullet and a good heart. Spade told the crowd at the Mirage that he’s contemplating a sequel Joe Dirtier.

Most of his jokes were about women, dating, sex, which I found encouraging. Slipping backstage I told myself it would be easy to ask about his secret after he’d been dancing around the subject for the last hour. I also assumed he’d be going out, hitting some bar or VIP lounge, and again I eagerly anticipated tagging along, watching the king hold court.

I found Spade in his dressing room, relaxing with a couple of buddies. The vibe was mellow, subdued. He seemed wrung out. Suddenly a mob of extremely attractive, extremely tall women came crashing through the door, like a home invasion of models. Friends of Spade, the women had driven in from L.A. They were all tipsy, and their ringleader was tipsiest. She was sipping alcohol through a straw as thick as a radiator hose, which protruded from a plastic cup the size of a flowerpot. She had a flushed, vodka-enhanced glow that nicely complemented her everyday glow. She was so radiantly pretty, in fact, that my breathing became shallow. I tried not to stare at her dark hair, her pale skin, her freckle-specked button nose, her deep, wide brown eyes set between what used to be called “buggy whip lashes.” A gray sweater, loose and unbelted, hung well below her waist but couldn’t conceal her figure (an iron lung couldn’t conceal her figure), and her black tights, which were skintight, painted-on tight (unhealthily tight, frankly), accentuated the most shapely pair of long legs I’d ever seen.

Spade gave her a brotherly hug and asked if she’d liked the show. Lurved it, she said, pulling another six ounces of booze through her straw. He posed for a photo with her, then with her friends. It was someone’s birthday. “Happy birthday,” Spade said. He thanked everyone for coming and announced that he was heading upstairs to bed.

We’re not going out? The air suddenly went out of the room. Black Tights frowned. Her friends frowned. I wanted to sit on the floor and weep. Everyone slowly marched into the hall. Spade went right. Black Tights and her posse veered left. I watched Black Tights disappear around the corner and tried to imagine what kind of woman Spade was seeing, or seeking, if Black Tights didn’t make his cut.

I trotted after Spade, reminding him that I needed to ask a few more questions before I could write my profile.

He scowled. Didn’t we cover everything the other night at dinner?

Just a couple more things, I mumbled.

OK, he said with a shrug.

We agreed to meet up again in L.A.

I sprinted back in the direction of Black Tights, catching up with her in the casino. I came up behind, a dinghy coming alongside a yacht. Ahoy. Panting from my wind sprint, I explained that I was writing about Spade, especially his effect on women, and that I’d like to interview her. (And maybe afterward, I thought, marry you?) How do you know David? I asked.

He comes into the restaurant where I work.

I handed her my card and asked her to give me a call

OK, she said.

She didn’t call.

I dropped by the restaurant a week later. She was standing inside the door. By the cold light of day, with less Vegas makeup, wearing jeans instead of black tights, she had a more wholesome girl-next-door quality—provided the girl next door was one of the most beautiful women in town.

I lost your card, she said. Sorry, I was pretty drunk that night.

No problem, I said. But listen, I’m still writing about David, and I’d still like to interview you.

Again I gave her my card.

Then I asked about her. What was her story? She seemed flattered. She said she was an aspiring actress from Ohio, where she’d studied theater in college. She was taking one shot at Hollywood, giving it everything she had, but she wasn’t going to play the fool or waste her life. If she couldn’t make it in two years, she was taking herself back to Ohio.

Any producer who doesn’t cast you is insane, blind, or dead, I wanted to say, but of course I couldn’t say that. I wondered what I could say, what Spade would say. I wished I’d asked him the secret when I’d had the chance. While I wished, while I wondered, Black Tights looked around and said she’d better check on her tables. She promised she’d give me a call and waved my business card to show me that she had it and was putting it in a safe place.

She never called.

The fourth time I tried to learn Spade’s secret was when I phoned his friend Courteney Cox Arquette. I’m writing about the greatest ladies’ man of all time, I said. David Spade.

She guffawed.

“Everytime I see David,” she said, “he’s always with a beautiful girl! I saw him recently with a girl. She was the most gorgeous, gorgeous, nice person I’d ever seen.”

I asked if she had any explanation for Spade. She didn’t hesitate.

“He’s funny.”

There it was, that most durable of urban legends: Women prize a sense of humor above all other qualities.

Right, I said. Funny. Carrot Top is funny, and somehow I don’t see women throwing themselves at Carrot Top.

“I don’t really know anything about Carrot Top,” Cox Arquette said.

She launched into a thoughtful sidebar on the merits of Carrot Top, choosing her words with care, as if she feared Carrot Top might be listening in.

Let’s set aside Carrot Top, I said. There must be something more to Spade than his sense of humor.

“I like his teeth,” she said. “He has good teeth.”

Funny and toothy? That’s it?

She fell silent.

“He’s smart,” she added. “You have to have a full package.”

Now we both fell silent.

“That sounded weird,” she said. “I’ve never seen his package.”

Still single at 42, I couldn’t deny there was more than journalism, more than a lifelong curiosity, lurking beneath my half-dozen attempts to learn Spade’s secret.

In my twenties and thirties being single was fun. When it wasn’t fun at least it was funny. I could always make my friends laugh with the story of my latest bad date. The anti-Semitic ballerina. The unhygienic medical student. The heavily medicated (though not nearly medicated enough) urban planner. I killed at parties with my story of the woman who was physically unable to kiss (it was like being pecked by an angry chicken). Or the woman who refused to take off her trench coat during dinner (it was like eating with Columbo’s younger sister). Or the woman who ended every story, every sentence, every last blessed utterance, with the same threadbare phrase: “Ex-cuse me? I don’t think so!” (As in, “So my father says I’m going to have to start making my own BMW payments, and I’m like, ‘Ex-cuse me? I don’t think so!”)

Then there was the woman who, in the first five minutes of our first date, asked why I left my native New York. As I began to explain, she shouted, “Rehearsed answer! This is a rehearsed answer!”

For years I laughed off all bad dates, all bad relationships, telling myself it was only a matter of time before the right date, the right one, came along. Upon turning 401 stopped laughing and started asking myself, What if the right one never comes along? More ominous: What if she’d already come along and I’d blown it? What if, in the midst of all those bad dates and cul-de-sac relationships, I’d actually met the right one, on a plane, in a coffee shop, backstage at a Vegas show, but flubbed my chance because I hadn’t achieved the requisite mastery, hadn’t learned the secret? What if the problem wasn’t my timing or my luck—but my game?

Most men think about their game. Most men look to improve, even married men, if only to feel better about themselves. A 42-year-old bachelor, however, thinks differently about his game. If a 42-year-old bachelor fears that his game is off, that his game needs work, he’d better fix it, fast, or it will soon be game over. He’s approaching that make-or-break moment, 45 years old, which Jerry Seinfeld calls “the Jesus Christ Age.” That’s the age, Seinfeld notes, when everyone around you says, “Jesus Christ, you’re 45 and still single?!”

I saw Spade, therefore, as more than an interesting subject. I saw him as a guru, a mandarin, a Merlin, and I viewed any advice he might offer as magic wisdom that could help me finally pull the sword from the stone. More than anxious to know Spade’s secret, I was intent, and the reason wasn’t that I wanted to be a ladies’ man but that I still clung to a fading belief in love.

The fifth time I tried, Spade was half naked. We were on the set of The Showbiz Show with David Spade (which has since been canceled). I was waiting for him to finish filming a sketch, and then we were going to sit down for that final wrap-up interview. He was wearing a red robe. I turned for a second to say something to someone, and when I turned back around the red robe was on the floor.

I flinched. Oh Lord no, I thought. I’d wanted him to reveal himself, but not like this. I’d hoped to discover why he was the greatest ladies’ man of all time, but I had no interest in seeing what all the ladies see just before the lights go out. I looked up, down, side to side, and started to blink rapidly, as if I’d just put in eyedrops. Between blinks I saw a jumpy montage of Spade’s parts. Bare shoulders, bare chest, fuzzy navel. Tattoo of Calvin—or was that Hobbes? Then I froze my face into that zombie stare men use when walking through a locker room, to avoid even a millisecond of direct eye contact with another man’s wood, and forced my gaze downward.

Luckily Spade was still wearing his baggy True Religions. Three sizes too big, they rode so low that I could see his underwear. I didn’t want to see his underwear, so again I made the zombie face.

Spade, meanwhile, was cracking one joke after another about his physique, disarmingly comfortable in his own skin. He was playing a sketch in which he posed nude for a painter, and with mock defensiveness he declared, “Hey, the canvas adds ten pounds!”

After a time I went and stood in the shadows with one of the makeup artists, a woman so lovely that she didn’t need a speck of makeup. My appreciation for this irony must have been written across my face, must have been scrolling across my forehead like the news ticker in Times Square, because she asked somewhat fearfully who I was. I told her I was writing about Spade. We chatted about nothing. I made her laugh. She made me laugh. I was just about to ask if she liked Edward Hopper paintings and Russian novels and long walks in the rain when Spade or one of his people waved to her. She was needed. Over There. She dropped me and hurried to Spade’s side.

Watching Spade speak to her, then to his assistant, then to his writers, I was struck yet again by his stature and its stark juxtaposition with his swagger. At five foot seven, a mere 67 inches, he stood the same height as when we were seniors, but he seemed to tower over everyone, maybe because he had that same unshakable confidence. Spade’s size, I thought, might be the reason he sends some men into paroxysms of jealous rage. He flouts the rules that are supposed to govern male competition—and isn’t competition the other name of the game?

Men perceive their fellow men, all their fellow men, as competition, rivals in the fight for precious resources, like money and mates and beer. While some forms of competition can call forth a man’s finest qualities, all competition awakens his most ancient anxieties. Study after study shows that any contest, whether a gunfight or a game of Go Fish, floods a man’s bloodstream with testosterone, that primordial Red Bull, which tells his brain it’s time to rise, to strive, to kill or be killed. Competition essentially brings out the silverback gorilla inside every man, particularly competition in which he loses: A man will more readily accept defeat if the victor is larger and shinier. Losing to someone notably smaller and less handsome plays hell with a man’s sense of identity and jungle justice. You’ll rarely hear men begrudge Tom Brady his languorous hours with Gisele Bundchen. At six foot four, with Cary Grant’s chin and 50 Cent’s abs, Brady is manifestly a top gorilla. But let Spade steal Gisele—a distinct possibility in my book—and you’ll hear men everywhere screech and beat their chests, in confusion as much as protest.

I made a note to ask Spade about his views on competition, on size, and above all on confidence, which I began to suspect was central to his secret. I was minutes away.

Then the sketch ended, and Spade was whisked off by his people. There was some problem that needed his attention. Over There.

Sorry, he said to me.

Racing after him, I asked if he was free the following day. Still a few last questions, l said. Shouldn’t take long.

Sure, he said over his shoulder, with obvious reluctance. He guessed he could do a quick lunch interview in his office.

He would give me one hour.

The first time I ever tried to ask Spade about his secret was actually years ago, at our 20th reunion. I’d skipped all previous reunions but decided to attend the 20th, curious to see two old faces. The girl to whom I lost my virginity on Camelback Mountain. And Spade.

The girl didn’t show. Spade did.

He strode into the banquet room of the Doubletree resort in Scottsdale leading a conga line of tall, stylish women. One was his date, a young actress who by rights should have set off the Doubletree’s sprinkler system. Spade spotted me and smiled. He walked straight over. He was wearing baggy jeans, a Blue Oyster Cult T-shirt, and Vans.

“Dude!” he said, sounding more Spicoli than Spade. He seemed tired, maybe a little drunk. “Are you still smart?”

“Smart? No, I gave that up.”

“Me too.”

I was all set to say, “Are you still—the king?” I was on the verge of congratulating him on his career, comedic and romantic, and asking, “Hey, what the hell is your secret?” But one of the women broke free of the conga line and grabbed Spade. He was needed. Over There.

“We’ll catch up later,” Spade said to me as she pulled him away.

I turned to talk with another classmate. She was tall, blond, poured into a sleeveless peach-colored dress. Almost Spade worthy. I didn’t remember her from high school, and she didn’t seem to remember me, which worked to my advantage. The conversation was going well. She was touching my arm, telling me a story. Suddenly she spotted Spade, momentarily alone. She stopped midsentence and flew to him like a trailer toward a tornado.

The sixth and final time I tried to learn Spade’s secret was in his office, over salads and iced tea. This time I didn’t hem and haw, didn’t bother with any warm-up.

I can’t help but notice, I began, that you tell a lot of jokes about dating.

Talk about what you know, he said with a sly smile.

If he were married, he said, he’d do jokes about marriage—and he’d probably do better with critics. “I’ve talked to Chris Rock about this, and even Sandler: I think people look at someone single and go—you don’t get it all. You don’t get the good reviews and get to date. And believe me, ! feel that about certain people. If Colin Farrell was going to start a singing career, I’d be like, I don’t like your album and I have not even heard it. You don’t get that, too. You don’t get to be a stud and a movie star and a singer.”

Speaking of studs. I kidded him about being surrounded by pretty women. His assistant, for one. And that woman in his dressing room.

He squinted. Who?

Vegas? Black tights?

Oh, right, he said distractedly. “Well, the problem is, my publicist is pretty, my assistant, my hair girls are all cute—one more reason to hate me. I meet a lot of pretty girls. The ones I actually trick into liking me back, somehow I still screw it up. That’s my fault, I have to admit that it’s a weak spot. I’m pretty good at work, I work hard on my act, I work hard at the shows, I try to take care of my family, try to take care of my friends, but everyone’s got a weak spot. My weak spot is—I can’t seem to nail this.”

What did he think was the cause of this weak spot?

“It’s not like I have my choice. I have a million girls tell me to buzz off. I’ve had girls go, Keep talking, I’ll fucking never like you, so please, whenever you’re done …”

I told him I wasn’t buying it. I knew his history. I was there at the beginning. I saw, with my own eyes. Tiffiny Lendrum.

He waved me off. He never really dated Tiffiny. He didn’t score much at Saguaro. “They’d have sex with their boyfriends all night and then come tell me how horrible they were.”

His tone darkened.

“I think it’s funny how people on Web sites are mad because I’m not good-looking. How about a high five that I’ve got to pull some other tricks out of my ass to get someone to go to dinner?”

Tricks. That word again. Could he be more specific? What tricks? What one tip or bit of wisdom would he give a single guy?. He paused. He pondered. Here it came.

“Someone who actually gives a shit about you is harder to find than you think.”

We both stabbed at our salads, chewing, mulling.

“There are some I think are really pretty,” he said. “There are some that are really fun. There are some that like hanging out. But do they really give a shit? And the answer 99.9 percent of the time is—no. They wouldn’t save me from drowning.”

So, besides a lifeguard who gives a shit, what else was he looking for?

“I like girls that are pretty, of course. That’s my crime. I love how shocking that is to people.”

Fine. Good. And when he found this pretty lifeguard who gave a shit, how would he win her? For the love of God, man, the secret.

“I think my only trick is—”

He took another bite of salad. I held my breath.

“—be normal and kind of have your shit together. And be consistent and reliable. Just not a flake. Really, the thing is, not to be a superflake. Don’t be an asshole. Don’t be supercocky. Don’t be a show-off. Everyone for some reason feels the need to show off. The only reason I learned that is, I get guys treating me like a chick. Guys that come up to me in a club or a bar and give me their card, they know they’ve got about 30 seconds before I start to drift off on them, because there’s really no reason that after 201 need to meet a guy for any reason. They’re like, ‘Hey, dude, we should hang out. Give me your number.’ I go, ‘Give you my number?! Aren’t you a guy?. What are we going to do, go to the Grove?’ They pull their phone out and stare at me and start typing. I’m like, Wait—it happened so fast! i almost feel like a girl sometimes. They basically want to separate themselves from the other cattle in 15 seconds. I see how girls get it: Dude, I run a company I’m not like these guys, I’m a super big shot, I own a Ferrari, i do all this shit, I get in everywhere. I realize how gross it is.”

He got on a roll. He said that being a child of divorce had made him gun-shy as a young m an. Then he’d watched close friends go through their own divorces, emerging years later, “ghosts” of their former selves, and he’d grown still more cautious. He doubted that he had the stomach to endure a divorce, so he took precautions, maybe too many. “To skip the good part in order to skip the bad part maybe isn’t the best plan, but it keeps me semi-sane.”

He talked about his absent father, his fear of becoming like his old man. “I know that’s a huge part of it,” he said. “The roughest thing a chick can do is pull out ‘You’re just like your dad.'”

Girls who give a shit never say such things, he added quietly.

I was shocked. All those women, all those choices, all that game, and he’d arrived at the same crossroads where I stood. He was a 42 year-old bachelor, a child of divorce, plagued by doubts, fearing that time was no longer on his side. He wasn’t merely my fellow bachelor from the class of ’82. He and I were the Last Bachelors, the last of the unmarried Mohicans. My Merlin was me.

I asked if he’d ever been in love.

“I’ve been in love,” he said. When it ended, he felt changed. “I went poker-faced.” Now he kept his feelings hidden, under wraps, which reminded him of one last bit of advice for men trying to upgrade their game with women.

“The more they don’t know—helps.”

I left his feeling good. At last, the elusive secret. But when I got back to my desk, when I started writing, it all fell apart in my hands. With rising despair I flipped back and forth through the pages of my notebook. Be normal? Have your shit together? Don’t be an asshole? It was all common sense, Farmer’s Almanac stuff. There was no magic, no secret, and I blamed myself. I’d been so taken by Spade’s sincerity, so surprised by our common ground, our mutual frustration and exhaustion, that I didn’t press him. O walked away feeling good, but I didn’t have the goods.

I put the story in a folder, put the folder in a box, and put the box on a shelf. ! moved on to other things.

Then three months ago I read the big news. Spade had reportedly gotten a former Playboy Playmate named Jillian Grace in a family way. She was 22, born three years after Spade and I graduated from Saguaro. In a statement Spade acknowledged having a fling with Grace and promised to shoulder full responsibility if the child proved to be his.

I phoned his publicist and asked for a few minutes with her client. I wanted to revisit the profile, I said. Freshen it with a few follow-up questions. She said she’d run it by Spade.

I never heard back from him.

I didn’t blame Spade. His life was possibly starting over. Maybe he was settling down, buying diapers in bulk at Costco.

Or maybe not. A short time later I read in the gossip magazines that he’d spent the weekend with Jennifer Aniston. Weeks after that I saw a photo of Spade walking on a floury white beach with a stunning Australian actress named Nicky Whelan. He didn’t look happy. He looked tired, as if the white sand were quicksand.

Studying that photo I decided there is no secret. Or, to be accurate, there is and there isn’t. What Spade said is true. A man should be consistent, reliable, take care not to be a flaky show-off asshole. But all that virtue won’t make him a virtuoso unless he also possesses that ineffable something, that intangible quality, which eludes description, which can’t be shared any more than it can be explained. Whatever it is, Spade has it, and it might be getting stronger as he gets older, which is his curse as well as his blessing.

An image came to me then, a vivid fantasy, clear as my high school memories, and I had Spade to thank for it, not because he changed my thinking but because he validated it. I’d wanted his secret, but in the end it was enough, reassuring and motivating, just to know that he was a fellow seeker. He and I are standing together at our 30th reunion, maybe our 35th, each of us holding a drink. He’s with a woman who looks as if she gives a shit, as if she can and will save him many times from drowning. He claps me on the back and busts out his wallet, begins showing me photos of his kid, one after another, dealing them at me like playing cards. He’s beaming, telling stories that are like the kid stories all my friends tell me, equally boring and endearing. He seems happy, and we study those photos until there is nothing more to say, until a pleasant silence descends. Just for laughs I remind him about the secret. Did he hold anything back when I interviewed him? He gets a devilish look. He puts away his photos, glances at his wife, then leans in. “Between you and me?” At that moment, we’re interrupted. A woman, the woman, who loves Edward Hopper and Russian novels, rushes up and hooks her arm in mine. Sorry, she says sweetly to Spade and his wife—he’s needed. Over There.

Illustration by Eddie Guy