It was raining on a Friday morning when I met Bo Dietl at his office on the 50th floor of One Penn Plaza. Despite some shreds of cloud, Mr. Dietl—a homicide detective turned security consultant and media darling—had a clear view of the city below and, off in the distance, in the middle of the choppy harbor, the Statue of Liberty. Every surface of his office seemed to be covered with awards and framed pictures of Mr. Dietl with folks like O.J. Simpson and Bill Clinton. The day before, Staten Island Congressman Vito Fossella had admitted to having an extramarital affair resulting in a secret love child. “Poh, Baby!” blared an issue of the New York Post resting on a nearby chair.

“You know what I think the problem with relationships is?” said Mr. Dietl. “People search real, real hard for love, and the word ‘love’ is passed out—like my daughter, her friends, say, ‘Goodbye, I love you.’ Love, love, love—the word ‘love’ is thrown around too easily.”

He leaned back in his leather chair. He wore a blue shirt—made from the best Egyptian cotton, he told me—with a white collar. His cuff links were square sapphires lined with diamonds. On his hip, he wore a holstered Glock pistol. His round face was deeply tanned, tight and shiny, enhanced by well-kept white stubble.

“It’s nice to say you love someone,” Mr. Dietl continued. “But the truth of the matter is I’m 57 years old, and I never felt love until maybe I was 53 years old, and I was through one marriage, and I had two children through marriage, and I wasn’t exactly the best husband in the world, and what with my job being a New York homicide detective, and with all the rah-rah’s running around—I was a bad boy, I was a cheater, admittedly, and I wasn’t happy.”

Like the congressman from Staten Island, Mr. Dietl said he himself had a secret love child. Or two.

He went on, noting that he’s seen many good marriages torn apart by unnecessary adulterous affairs, frequently committed by bored, pampered wives. The key to a relationship, he told me, is communication. Especially in the bedroom.

“When you are making love, ask her what she likes: ‘Is this good?’” said Mr. Dietl. “Don’t think that because you are endowed with a large penis, you’re jumping on top and ramming and ramming, that you can make her feel great. You know the whole thing is about her feeling good.”

He gave me a serious look. “There are a lot of women,” he said, “who are not reaching orgasms.”

“People think it’s all about how long you do it, and this size bullshit,” he said. “You know what? Size doesn’t matter. … The majority of the women are not into 12- or 14-inch penises because it hurts them. When you are making love, and you have aroused her sexually, to that plateau, where every part of it is romantic, where you kiss all over the body from her head to her feet—that’s lovemaking. Not jumping on top and ram-a-dama ding-dong—that don’t mean crap.”

Mr. Dietl said he began dating his fiancée, Margo, seven years ago, but only four years ago did he realize that he was in love.

“To me, being in love with someone is you wake up, you go to sleep, thinking about that person,” he said. “She’s my best friend, she’s my soul mate, we think the same. The only problem is that she has the same personality as mine, so when there’s an argument, there’s no give, it’s like a car crash, head on. But I think we are starting to handle it, because we understand each others’ personalities.”

He gestured at a calendar girl in a bikini on the wall. “I can look at a Playboy playmate, 19-, 20-year-old, a hot, young tight-body babe, and you know, that’s there, that’s there, it looks good, and I’m a man. But if I weigh it out, and I weigh it with what I have …” He added that people shouldn’t be afraid of incorporating role-playing and pornography into their sex lives to keep things fresh.

I emerged from One Penn Plaza feeling woozy. Back at my office, I phoned someone who might also have some wise words on marriage, Raoul Felder, the famous divorce lawyer.

“You want my advice on marriage?” he said. “I got three words: Pre. Nuptial. Agreement.”

“The divorces are getting uglier, because there’s a certain quantum of anger in these relationships, and because divorce is becoming basically no-fault, they end up fighting about kids and money. And they get much meaner and tougher,” said Mr. Felder, 71.

And his own marriage? He and his wife are still married. What’s the secret?

“Fear. My wife is a divorce lawyer. I gotta run, kid.”

I decided to wade deeper into the waters of marriage. A voice at the other end of the line at Taki Theodoracopulos’ Manhattan residence informed me that the fabulously wealthy 70-year-old Greek columnist—renowned for his mastery of sailing, tennis, karate and womanizing—was taking calls on the second floor of his townhouse; a number was provided.

“I’m a European,” he said, “and I operate under European rules. I’m allowed to fool around; my wife is not. It’s as simple as that. And that’s why it’s worked for 37 years.

“We don’t fall for this American bullshit,” he continued. “Wives, we put them on the plinth, we protect them, we support them.” He said he and his wife, Princess Alexandra von Schönburg, have an arrangement. “Obviously, if you have money, you can do that. If you can’t—and most people have to work—then the little women, as they used to call them, have rights, too, and they have to be 50-50. But in my case, let’s say I was lucky, and I’ve had it my way.

“Obviously, my wife—who’s an Austrian and a German princess—I don’t do it openly, but she obviously has heard things and she obviously was upset,” he said. “But you don’t break up a family, because men are promiscuous by nature, and that’s it.

“I don’t think you can live having equal rights within a family,” he went on. “There has to be a boss. You can’t have two superpowers—one is bound to collapse. Communism did. This equality thing doesn’t work in a family.”

New York, he said, is prime example of the dangers of equality.

“From the New Yorkers I know, I can’t think of anyone who hasn’t been divorced,” he said. “All my friends—people who I’ve liked, gentlemen—most of them have been divorced. And the ones who haven’t been divorced, are Europeans who live here. Very strange, that.”

How are things going with the Princess, by the way?

“Very happy, extremely happy,” he said, speaking for himself and his wife, who was a continent away. “As I get older, even happier, I chase less pussy.”

I swiveled to a great American: Gay Talese, who is married to editor Nan Talese.

“Next year will be 50 years in the same house with the same woman,” said Mr. Talese, 76. “So the trophy bride is in her early 70s.”

“What helps a marriage is space,” he said. “One of the great things that Nan and I have had from the year we got married is more than one bathroom.”

Also, each morning she goes off to her office and he goes to his—a converted wine cellar beneath their townhouse on East 61st Street. When they sit down for dinner each night at 7, it’s like a date.

“It’s like a 50-year-long date,” he said.

I called former Andy Warhol acolyte Bob Colacello, who’s 61 and great pals with Nancy Reagan.

“In the abstract, I think divorce is wrong, and it’s better to stay married and make an arrangement, like they do in Europe,” he said. “But then, in the concrete, I have friends who have been divorced, have fallen in love again or divorced because they fell in love with someone else, and they’re much happier for it, and eventually the spurned spouse seems to land on his or her feet and they are happier for it, too. It’s so hard to generalize about marriage. I do think the younger generation seems to get divorced real quick.”

Why is that?

“I think I’m probably going to get in trouble with the feminists, but I think women expect too much these days, out of life—or are trying to do too much, maybe. But in Manhattan, in New York society, or so-called New York society, it’s so competitive on every level—in terms of money, in terms of publicity, in terms of houses and planes and yachts. This whole phenomena of trading up.

“In the ’80s, it seemed like it was the husbands trading in the wives for newer models,” he continued. “That’s when the phrase ‘trophy wife’ emerged. In the early years of this new century, it seems like it’s the women trading in the husbands, because the husbands don’t quite match up to their expectations, whether it’s financially, or romantically, or in glamour or in publicity.”

And then there’s gay marriage?

“I think gay marriage is going to be great for the gay divorce lawyers,” said Mr. Colacello.

It was only a floor below the ballroom where Rudy Giuliani held a fund-raiser for his presidential campaign.

On his way out, Bloomberg ran into longtime Giuliani supporter (and former roommate) Howard Koeppel. Or, more accurately, Koeppel almost physically ran into Bloomberg -- who basically owes the start of his political career in large part to Giuliani -- and promptly told him why he thought an independent candidacy was such a great idea.

“I told him that if he runs, he’ll help Rudy, because he’ll take votes away from the Democrats,” said Howard Koeppel, a longtime Giuliani supporter.

“‘Don’t worry,” Bloomberg responded, according to Koeppel, who had slung his arm around the mayor.

“I’m not running.” The mayor told Koeppel that he was running late as he made for the black SUV waiting for him on the street. Koeppel, an acquaintance of Bloomberg’s going back to the mayor’s first campaign in 2000, offered the mayor a friendly smack on the back of the head.

As Bloomberg made for his car, Koeppel, the gay Audi salesman in whose apartment Giuliani stayed during the former mayor’s divorce from Donna Hanover, rejoined his friends against a wall in the lobby. He stood next to Raoul Felder, Giuliani’s divorce lawyer, and Christopher Lynn, Giuliani’s former transportation commissioner.

After Koeppel recounted the exchange for reporters, Lynn interjected that he, for one, thought a Bloomberg candidacy a terrible idea.

“The biggest tax raises in the history of New York was hoisted on us by Mike Bloomberg. How do you think that is going to resonate?” said Lynn, who waved around a pamphlet distributed at the Giuliani fund-raiser upstairs. It said “Rudy” and listed the former mayor’s “12 commitments,” the promises he guarantees to keep if elected President. “The first three years he ran the city how did he run the city? Borrow and spend borrow and spend, borrow and spend.”

Koeppel was asked by a few reporters how he knew Bloomberg.

“Rudy asked me if I would help him, so I sat with him at some ball games,” said Koeppel.

“He didn’t ask for any help!” screamed Lynn.

“No, not financially,” said Koeppel.

Felder mumbled something incomprehensible and stiffened.

“And he yelled at you that time, remember? At John Ravitch’s fund-raiser. And you said, ‘Mike, I would have helped but you didn’t ask,’” said Lynn. “And he said 'Howard, the only one who ever helped me is that guy right there – Pataki.' And you said ‘Mike, you didn’t ask.’”

They were asked if any of them had discussed the merits of a Bloomberg candidacy directly with Giuliani? Koeppel raised a finger to his lips and the three men headed out.

Earlier in the evening, Bloomberg received less ambiguous support. Shortly after 7pm, Bloomberg walked up the stairs of the Sheraton surrounded by secret service his security detail and his closest political aide Kevin Sheekey.

At the top of the stair, in front of the second floor ballroom, he stopped for a quick chat with Stuart Appelbaum, the Jewish labor activist who was hosting the event Bloomberg had come to speak at.Appelbaum was effusive with praise about the mayor’s new independent affiliation and the prospects that it opened.

“I’m in awe,” said Appelbaum.

“We’ll see what happens,” said Bloomberg, nodding his tilted head, shrugging his shoulders.

Inside the ballroom, Appelbaum introduced the mayor to the hundreds of attendees of that evening’s dinner as a leader by saying that people had always wondered what kind of Republican Bloomberg was: “Tonight we can tell them, he’s the very best kind -- he’s a former Republican.”

Bloomberg’s speech made no reference to the presidential ambitions he makes a point of denying, preferring to stick with union material.

“The truth is that Jews and labor have been linked together since my ancestors were building pyramids in Egypt and were paid nothing for it -- not a very good labor contract,” Bloomberg said.

At that point a woman in the back of the room stood and screamed something in protest, calling the mayor a “pickpocket.”

“OK, we have plenty of time miss,” the mayor said. “I’ll be happy to stand here -- my next event isn’t for another few minutes. Thank you for sharing your views. Here I am, 4,500 years later, working for a dollar a year. And getting yelled at.”

The crowd laughed and Bloomberg introduced one of the night’s honorees, Bruce Raynor, a co-president of the hotel and garment workers' union. With Bloomberg seated next to him, Raynor noted that Giuliani was raising money in a nearby ballroom. It was clear which of the mayors he preferred.

“The former mayor is still a Republican, always was a Republican -- divisive and mean,” Raynor said. “I wasn’t sorry to see him leave and I won’t be sorry when he loses the Republican nomination.”

Bloomberg, sitting quietly, did not offer a visible response.