Illustration by Michael Byers

The onset of middle age used to mean that one could ease into becoming a bland old fusspot, free from the burden of remaining attuned to the microscopic upticks of the cultural barometer. You’d have bought a reliable European sedan, started making bad jokes to waitresses and receiving all your news from Time. Blissful irrelevance was the calling card.

But thanks to a confluence of factors, the generation gap that once created a comfortable buffer between youthful folly and mundane adulthood has all but eroded. Instant Internet access to the entire history of popular culture has played a role. There’s also the trend toward flat, decentralized workplaces, where those of us who watched the Nixon impeachment sit in open offices next to co-workers who were still teens when the first African-American president was elected. And not least of all is the fact that so many 40-somethings—men and women of my generation—refuse to act their age.

We now exist in a timeless culture. As media theorist Douglas Rushkoff argues in his new book, Present Shock, there is no past or future—only right now. “The present isn’t so much a culture of its own as it is an amalgamation of all the periods we’ve been through,” said Mr. Rushkoff. “And this makes it difficult to belong to a particular generation.”

The old generational identities that once defined us have broken down, and the net result is a messy temporal mashup in which 40-somethings act like skateboarders, 20-somethings dress like the grandfather from My Three Sons, tweens attend rock concerts with their parents and toddlers are exposed to the ethos of hardcore punk.

It didn’t used to be like this.

“I worked at Limbo cafe on Avenue A in the early ’90s, where The Paris Review would do readings for the drag queens, squatters and smackheads,” recalled Michael Rovner, a 42-year-old former magazine editor who is now a principal in the content marketing agency Mr. Finn Content Works. “These 45-year-old swells from the Upper East Side would show up, and it always seemed like they were crashing our party. But now I’m in my 40s and younger people don’t look at me that way. I can go see Sky Ferreira at Glasslands, though I suppose I do run the risk of being called ‘sir.’”

The lines are blurred, the edge has been dulled and the traditional time lines have been jumbled. We all now feed from the same cultural trough. And while the Baby Boomers are busy preparing their sloops for that sunset sail into retirement (provided their 401ks haven’t taken on too much water), the graying of Gen X has been postponed indefinitely.

While the erosion of the generation gap may seem like a positive step for society—longhairs trusting people over 30, Archie Bunker making peace with Meathead—the liberation provided by this breakdown is largely symbolic. As Mr. Rushkoff put it, “Culturally, everything is just one level deep, one search away.”

“There are no longer the same generational divides, but I think that’s also because no one is experiencing much of anything in depth,” he continued.

Which is not necessarily a condemnation of our 140-character society, or the technology that wrought it. The Internet has unlocked the creative potential of humanity, and it is making people more accountable for their actions. But for me and many of my generational cohorts, this interconnectedness has also resulted in a lot of extra homework, as we’re now expected to keep up with every new ripple in the sea of culture.

You may know, for instance, that Skrillex is the EDM dude with the weird haircut that all the suicide girl baristas had last summer—a trend that, of course, has spawned at least one Tumblr. I didn’t. So I had to do a little studying, in order to communicate intelligently with my younger co-workers.

It may sound trivial, but maintaining all this awareness is tiring business. Though I feel neither old nor outmoded, I just turned 45. Assuming I manage to walk the Earth for as long as my recently deceased father did, the first half of my life is over. By even the most generous definition, I am middle-aged. As such, I tire easily.

And I’m not alone.

“It’s gotten exhausting,” said Kyle Smith, the 46-year-old author and New York Post film critic. “I have to keep up in some ways, otherwise my cultural references risk sounding like Grampa Simpson’s. But I’m also supposed to stay on top of reality TV, Homeland, everything on HBO, the latest politician’s gaffe and whatever’s trending on BuzzFeed, Vine and Twitter? I can’t do it. There aren’t enough hours in the day. And I just don’t have the desire.”

Illustration by Michael Byers

Even when we make an effort to avoid new information, it finds us, thanks to the constant stream of social media and the omnipresence of digital devices. Sure, some of this is self-imposed. And, yes, one could move to a remote cabin in Montana and do nothing but read the works of David Foster Wallace and annotate old perfect-bound issues of The Baffler, but there isn’t much money in that kind of thing these days.

Besides, if one were truly to unplug, one would run the risk of missing out on what Jezebel editor in chief Jessica Coen refers to as “eye-opening intergenerational experiences.”

“Whereas once it might have been easy to slowly disconnect from pop/youth culture and fade, blissfully ignorant, into irrelevance, now ‘disconnecting’ means literally to deny yourself the full experience of a dominant cultural medium,” said Ms. Coen, who, at age 33, splits the difference between the Millennials and Generation X.

Some of my peers on the brink of middle age do succeed at ignoring the noise. Stephen Metcalf, a Slate contributor and author of the forthcoming Junk, about the unexplored relationship between Reaganism and pop culture, feels the greatest gift he’ll give to coming generations is his out-of-it-ness.

“I’d love to not seem like a used-up husk,” he said. “But realistically, if it hasn’t been on NPR’s Tiny Desk Concerts, I haven’t heard of it.”

As an aspiring fuddy-duddy, Mr. Metcalf suspects that Generation Xers aren’t the only ones who are suffering due to the loss of the generation gap. “There’s no more ‘gap’ in the traditional sense,” he said, “but isn’t this just another theft, courtesy of the Boomers? Isn’t the Alternadad taking away his kids’ turn at self-definition?”

Take rock concerts, for example, those smoke-filled dens of electrified wizardry which young people used to seek out in defiance of their parents. Now they’re family outings. If you’ve been to venues like Madison Square Garden or the Barclays Center recently, you’ve probably seen second-graders rocking out to Canadian power trios and aging British quartets right alongside their guardians.

One wonders what the result of all this generational commingling will be. Will our children be forced to go to further extremes to rebel? Or maybe they’ll become archly conservative boors in response to all of this enforced hipness—the mature grown-ups we’ve not yet had the guts to become.

It would serve us right.

I know that I’m part of the problem.

My nearly 5-year-old son is well versed in the lore of the Ramones and could offer a dissertation on the original Star Wars trilogy. His younger brother recites the lyrics to Beastie Boys songs like they were nursery rhymes. I have introduced them to the cultural totems I once cared about, but I wonder if I am shortchanging them in the process. Not to mention infantilizing myself.

(This topic was covered some in Neal Pollack’s Alternadad: The True Story of One Family’s Struggle to Raise a Cool Kid in America, in which he takes his toddler to the Austin City Limits festival, among other generation-sharing adventures.)

But maybe that’s the key. There does seem to be a deeper fear of growing up for men and women of my generation—an insecurity about what comes next. Many of us can’t say with confidence whether we’ll have a job in 10 years. Or what our bank accounts will look like in 20. Retirement will be, for many, an impossibility. So perhaps as long as we act like kids, we can deceive ourselves into thinking we are still young, that we have at least one more chance to get it right. Even if, in so doing, we abdicate our roles as serious, solid citizens. As adults.

I know guys whose style of dress and off-duty interests haven’t changed a lick since college. They devote their free time to movies about comic-book heroes, to video games and to fantasy football. No, they aren’t hurting anybody. But perhaps what we really need to do is put on suits and take our wives out for expensive dinners, like our dads before us.

My father was 45 when I was born—the age I am now. Though he was always youthful and athletic, even to the end, he was a child of the Great Depression, a first-generation American Jew who grew up poor and scrappy in a shared rental duplex on Detroit’s west side. He seemed to have become an adult the day he graduated law school.

In his early 50s, my father was a dark-haired force of nature in double-breasted suits who was as feared in the courtroom as he was generous outside it, and my view of what adulthood is supposed to be is modeled on this snapshot of him. He seemed older and more respected than I can ever imagine being.

When my father wasn’t working—and he was almost always working—he was reading the evening papers, listening to baseball games on WJR radio or watching old cowboy movies. The things I was interested in—punk rock, BMX bikes and National Lampoon—were simply not on my father’s radar. I didn’t take this as a lack of interest. He was loving and warm and present. He just seemed too adult to have an idea that things like Black Flag or Foto Funnies even existed.

He had his interests and I had mine. The difference was that, like most of my generation, I became defined by those interests. And have been ever since.

Perhaps what is truly lost with the erosion of the generation gap is this sense of actual adulthood—the maturity to stop caring what my interests in pop culture say about me; the comfort in being seen not as an equal, but as an elder (even if my younger co-workers stop asking me out for drinks). As Mr. Rushkoff told me, “Maybe that’s the generation gap we’re longing for—the permission to let go of the search.”

But within a day, the Los Angeles Times story that broke the news had snowballed into Gropegate, forcing the neophyte politician to reverse his strategy. Following in the footsteps of guilty parties as different as Richard Nixon, Hugh Grant and Capt. Joseph Hazelwood of the Exxon Valdez, Mr. Schwarzenegger asked the public to forgive him. His apology is reproduced in My Bad, an amusing compendium of mea culpas assembled by humorist Paul Slansky and Arleen Sorkin, an actress, producer and television writer.

“Yes, it is true that I was on rowdy movie sets and I have done things that were not right which I thought then was playful but now I recognize that I have offended people,” the candidate said during a campaign stop in San Diego. “And to those people that I have offended, I want to say to them I am deeply sorry.”

Four days later, he was elected the 38th governor of the most populous state of the union by a huge margin. Apparently it mattered little to the voters in California that the actions for which he was apologizing, downplayed to make them seem like harmless tomfoolery and relegated to the anything-goes terrain of the movie sets, offered troubling insights into his character. In a culture that nurses at the bosom of Oprah and her treacly theater of confession, deliverance can be bought for the price of a well-planned public-relations stunt. The content of the apology and the nature of offense matter less than the hollow posturing, which also conveniently functions as the final word in the public record of these disgraceful, idiotic or harmful missteps.

It’s our present immersion in the Era of the Insincere Apology that inspired My Bad, which sets out to examine the “sheer volume of wrongdoers rushing forward to get their repentance on record, and the culture’s willingness to grant them speedy pardons despite the obvious lack of sincerity that imbues most of their efforts.” Unfortunately, while the authors cast a wide net, they aren’t interested in taking a hard look at this ubiquitous phenomenon. The book is a well-stocked anthology rather than a work of cultural analysis.

Organized by genre—13 separate categories of contrition are represented, including sports, show business, corporate America, politics, religion and the media—the collection is made up of hundreds of verbatim apologies, followed by short explanations of the circumstances which gave rise to them. Some of the commentaries are entertaining. For example, with respect to the terse apology of Ray Brent Marsh (the Georgia crematorium operator who was sentenced to 12 years in prison for dumping bodies instead of cremating them), the authors wonder why his chosen disposal technique was more appealing to him than simply using the crematorium. Often, however, the commentaries are too short to provide any real insight or context.

Many of the boldface personalities you’d expect to find in such a book turn up on cue, including Bill Clinton (for both the Lewinsky affair and an incident involving gay politicians greeted by Secret Servicemen in rubber gloves); Pete Rose (for gambling on baseball); Marge Schott (for being a racist baseball owner); Roseanne Barr (for spitting and grabbing her crotch during the singing of the national anthem in 1990); Russell Crowe (for his recent misadventures in a Soho hotel lobby); Bill O’Reilly (in a lukewarm non-apology over the fact that he was wrong about W.M.D.’s in Iraq); Mike Tyson (for biting the ear of Evander Holyfield); and, of course, Ted Turner (for being Ted Turner, many times over—he scores more coverage than anyone else in the book).

There are some glaring omissions, including Robert McNamara’s long-awaited mea culpa for his role as the architect of America’s involvement in the Vietnam War, delivered in the form of a 576-page memoir. On a related note, My Bad also inspires one to think about apologies we’re still waiting for. Two entities with roots in Houston—the Bush administration and the Enron Corporation—come to mind as flagrant non-apologizers (though in fairness, W. does have one citation in the book, for an apology made to an Egyptian newspaper following the Abu Ghraib prison revelations).

Just as interesting are the apologies that seem completely unnecessary, usually delivered because of commercial pressure or political correctness. ABC’s pathetic pandering over Janet Jackson’s infamous “wardrobe malfunction” is the most notorious of these, but just as silly is the fact that the president of the Fox Network had to apologize in 1992 for a song featured on a Simpsons episode, which referred to New Orleans as “crummy, lousy, rancid and rank.” In response to the uproar, the executive was forced to explain that the song was “a parody of the opening numbers of countless Broadway musicals.” Satire? In a Simpsons episode? Say it ain’t so.

Many of the apologies included in My Bad reflect the fact that we live in what Robert Hughes referred to as a culture “where evil and misfortune are dispelled by a dip in the waters of euphemism.” It’s also true that more people are forced to apologize today because more misdeeds are being exposed by the ever-encroaching media, endlessly hungry for fresh scandals. (Would James Frey have been outed had A Million Little Pieces been published a decade ago, before the advent of Internet? Quite possibly not.) These are points worth exploring.

Do the authors regret that they failed fully to investigate these issues? Are they sorry that their book is an entertaining if inevitably redundant catalogue? Perhaps they’re planning to issue a formal apology.

Peter Hyman is the author of The Reluctant Metrosexual: Dispatches from an Almost Hip Life (Villard).

But within a day, the Los Angeles Times story that broke the news had snowballed into Gropegate, forcing the neophyte politician to reverse his strategy. Following in the footsteps of guilty parties as different as Richard Nixon, Hugh Grant and Capt. Joseph Hazelwood of the Exxon Valdez, Mr. Schwarzenegger asked the public to forgive him. His apology is reproduced in My Bad, an amusing compendium of mea culpas assembled by humorist Paul Slansky and Arleen Sorkin, an actress, producer and television writer.

“Yes, it is true that I was on rowdy movie sets and I have done things that were not right which I thought then was playful but now I recognize that I have offended people,” the candidate said during a campaign stop in San Diego. “And to those people that I have offended, I want to say to them I am deeply sorry.”

Four days later, he was elected the 38th governor of the most populous state of the union by a huge margin. Apparently it mattered little to the voters in California that the actions for which he was apologizing, downplayed to make them seem like harmless tomfoolery and relegated to the anything-goes terrain of the movie sets, offered troubling insights into his character. In a culture that nurses at the bosom of Oprah and her treacly theater of confession, deliverance can be bought for the price of a well-planned public-relations stunt. The content of the apology and the nature of offense matter less than the hollow posturing, which also conveniently functions as the final word in the public record of these disgraceful, idiotic or harmful missteps.

It’s our present immersion in the Era of the Insincere Apology that inspired My Bad, which sets out to examine the “sheer volume of wrongdoers rushing forward to get their repentance on record, and the culture’s willingness to grant them speedy pardons despite the obvious lack of sincerity that imbues most of their efforts.” Unfortunately, while the authors cast a wide net, they aren’t interested in taking a hard look at this ubiquitous phenomenon. The book is a well-stocked anthology rather than a work of cultural analysis.

Organized by genre—13 separate categories of contrition are represented, including sports, show business, corporate America, politics, religion and the media—the collection is made up of hundreds of verbatim apologies, followed by short explanations of the circumstances which gave rise to them. Some of the commentaries are entertaining. For example, with respect to the terse apology of Ray Brent Marsh (the Georgia crematorium operator who was sentenced to 12 years in prison for dumping bodies instead of cremating them), the authors wonder why his chosen disposal technique was more appealing to him than simply using the crematorium. Often, however, the commentaries are too short to provide any real insight or context.

Many of the boldface personalities you’d expect to find in such a book turn up on cue, including Bill Clinton (for both the Lewinsky affair and an incident involving gay politicians greeted by Secret Servicemen in rubber gloves); Pete Rose (for gambling on baseball); Marge Schott (for being a racist baseball owner); Roseanne Barr (for spitting and grabbing her crotch during the singing of the national anthem in 1990); Russell Crowe (for his recent misadventures in a Soho hotel lobby); Bill O’Reilly (in a lukewarm non-apology over the fact that he was wrong about W.M.D.’s in Iraq); Mike Tyson (for biting the ear of Evander Holyfield); and, of course, Ted Turner (for being Ted Turner, many times over—he scores more coverage than anyone else in the book).

There are some glaring omissions, including Robert McNamara’s long-awaited mea culpa for his role as the architect of America’s involvement in the Vietnam War, delivered in the form of a 576-page memoir. On a related note, My Bad also inspires one to think about apologies we’re still waiting for. Two entities with roots in Houston—the Bush administration and the Enron Corporation—come to mind as flagrant non-apologizers (though in fairness, W. does have one citation in the book, for an apology made to an Egyptian newspaper following the Abu Ghraib prison revelations).

Just as interesting are the apologies that seem completely unnecessary, usually delivered because of commercial pressure or political correctness. ABC’s pathetic pandering over Janet Jackson’s infamous “wardrobe malfunction” is the most notorious of these, but just as silly is the fact that the president of the Fox Network had to apologize in 1992 for a song featured on a Simpsons episode, which referred to New Orleans as “crummy, lousy, rancid and rank.” In response to the uproar, the executive was forced to explain that the song was “a parody of the opening numbers of countless Broadway musicals.” Satire? In a Simpsons episode? Say it ain’t so.

Many of the apologies included in My Bad reflect the fact that we live in what Robert Hughes referred to as a culture “where evil and misfortune are dispelled by a dip in the waters of euphemism.” It’s also true that more people are forced to apologize today because more misdeeds are being exposed by the ever-encroaching media, endlessly hungry for fresh scandals. (Would James Frey have been outed had A Million Little Pieces been published a decade ago, before the advent of Internet? Quite possibly not.) These are points worth exploring.

Do the authors regret that they failed fully to investigate these issues? Are they sorry that their book is an entertaining if inevitably redundant catalogue? Perhaps they’re planning to issue a formal apology.

Peter Hyman is the author of The Reluctant Metrosexual: Dispatches from an Almost Hip Life (Villard).

An example: Sarah Simms, a psychotherapist (so she should know better), was looking prim in a white pantsuit, walking through a collection of letters, photographs and personal items from New York's first great first ladies, Eleanor Roosevelt and Jacqueline Kennedy Onassis. The Transom inquired what pieces she found most interesting, and she said, "I liked some of the quotes, the excerpts, of when Hill-oh, when Hillary! When Eleanor, I mean, wrote to Jackie and when Jackie wrote back to Eleanor."

Her friend Virginia Mailman, outfitted in another Clintonesque power suit, added: "They were both wonderful. One was an activist, and one was what we expected the first lady to be. She was so feminine and so interested in all the feminine things. Eleanor Roosevelt obviously set the stage for Jackie-er, for Hillary Clinton."

What's going on here? The ever-suspicious Transom guessed: Perhaps there's been a plot to hypnotize every pearl-wearing woman on the Upper West Side, oversaturating them with Clinton 2008 gossip until it starts pouring out of their ears? Did someone slip lithium into the mimosas? Either way, the gathering had a distinct, hazy feeling of a Junior League pre-presidential Democratic fundraiser. Sensing we were onto something, we set out looking for Bob Shrum.

Instead we found Amy Weinstein, the associate curator of 20th and 21st century collections for the Historical Society. She explained that no, nothing insidious was afoot. The Eleanor/Jackie display was merely their companion exhibit to a touring show of first lady gear from the Smithsonian. Any women entranced by such items as Mrs. Roosevelt's 1957 gun permit or Mrs. Kennedy's Chapin report cards ("She would be well-liked by the other children if she were more kind and considerate of their rights," wrote her teacher Reba Wright in 1938), was so captivated of her own accord. Some of the ladies who lunch, who were lunching then in the library upstairs, agreed as they sat quietly awaiting a speech by Mrs. Clinton, to come later in the hour.

In the meantime, we wondered if the Historical Society would consider adding a Clinton to its display of great New York Presidential spouses. Without missing a beat, Ms. Weinstein smiled and said, of course, there's always room for memorabilia from "a First Husband-oh, um, from the First Lady, I mean."

-Rebecca Dana

Meet the Racist

"O.K., this is how it goes," said Ben Stiller at the top of yet another Off Broadway offering from playwright Neil LaBute, This Is How It Goes, which debuts at the Public Theater on March 26. Imagine Greg Focker after a game of Quarters with double espresso shots: "I mean, went. This is the way it all played out, or is going to. Or is, right now. Doesn't matter, you'll figure it out. I think. No, you will."

This is how the play goes: Ben Stiller, Amanda Peet (who stepped into the role when Marisa Tomei dropped out) and Jeffrey Wright form an interracial love triangle. Ms. Peet is married to Mr. Wright. Gasp! Mr. Stiller, whose crush on Ms. Peet dates back to high school, is a racist. Oooh. Mr. Stiller isn't really a racist. Aaah. Mr. Stiller is … oh, just go see the damn play if you want to figure it out.

The Late Nite Committee of the Public Theater hosted a special performance of the play on March 17, along with Steven Rubenstein, bespectacled heir to the Rubenstein Associates public-relations throne, Vanity Fair maiden Vicky Ward and LaBute alumna Rachel Weisz.

After the actors took their post-show bows, Stacey Bendet, owner of Alice and Olivia-whose name might be familiar to anyone who's ever glanced at an invitation from a benefit host committee in this city-bolted from her seat. Maybe she knew what was coming up next: an overly serious discussion moderated by Brent Staples, New York Times editorial board member, with the cast and the play's director, George C. Wolfe.

"Neil wants to implicate you in his machinations," Mr. Staples said in his lengthy opening. "He wants to pull you in and implicate you in his sense of the human self. As we've seen, his sense of the human is that, especially men, we are somehow-at the very core-a rotten kind of carnivores who play with our food. Carnivores usually kill to eat, but we play with our food and amuse ourselves at other people's distress." Uh, O.K.

Asked by Mr. Staples if he enjoyed the role of a carnivore who plays with his food, Mr. Stiller looked as if he would rather be getting tortured by his cinematic father-in-law, Robert De Niro-or getting his scrotum trapped in his zipper. "Did everybody have fun tonight?" Mr. Stiller said, delighting the crowd before turning serious. "I think he always poses a lot of interesting questions in his plays. I always find them very interesting, because there are aspects of us that are not usually paraded out in public. I find that to be what usually connects with me. He says things and has characters say things in plays that you don't usually hear said out loud." In this case, a few utterances of the "nigger" and one mention of "thick black cock."

Mr. Wright addressed the notion that Mr. LaBute fancies the audience as a fourth character-a word of caution to future theatergoers. "There were a couple nights [in previews] that I thought that it kind of ran away from us-us as playwrights, us as actors," Mr. Wright said. "The audience, I thought, got off a little easy in some ways. They were titillated by some things that I found … worrisome. I just wouldn't let them get away with it next time."

Ms. Peet answered the same question, but her piercing blue eyes were too distracting to hear the reply.

A short time later, a kindly-looking gray-haired woman piped up. "I think it's interesting that it's clear-and I hope I'm right-is that the writer is white," she said. "Isn't that correct? The reason I say that is because the white protagonist is the only the person really interesting in this play-complex and interesting. The black man is one-dimensional, very difficult to really believe, stereotypical, and I don't think the writer knows really much about black people."

"Neil LaBute's mother," Mr. Wolfe joked, nodding his head in the direction of the woman. The crowd was amused; she wasn't.

-Andrew Stengel

Euro Envy

East Village Wines, on First Avenue between St. Marks Place and Ninth Street, is the type of place where the co-owner inquires about his customer's "sweethearts" and runs product-giveaway contests for the most original palindrome. The store has been a fixture since the early 1960's, long before the neighborhood became a haven for iPod-laden hipsters and overpriced walk-up studios. But as the East Village has become more gentrified, so too have East Village Wines' fiscal policies. To keep pace with a globe-trotting clientele, the store accepts and exchanges euros, the currency that unites the 12 nations of the European Union and is currently slapping the dollar silly.

The store's euro guidelines were initiated by co-owner and currency buff Bob Chu three years ago, when the euro debuted in paper form (it has existed as an electronic-trading device since 1999). "We're not a bank," said Chu, a stocky Chinese-American with salt-and-pepper hair and a thick Bronx accent. "It's just a friendly bartering system. But you gotta take care of your customers."

The store doesn't advertise this practice, though most of the regulars know of the arrangement. For those who aren't aware, a small chalkboard near the cash register states the offering as well as the novel rate of exchange with matter-of-fact clarity: one U.S. dollar for every one euro.

Customers traveling to Europe can thus convert enough pocket money to get them to their initial destinations at a tidy profit, compared to rates given at a bank or airport kiosk (the current exchange rate is $1.32 for every one euro). Those returning from abroad can put the euros they inevitably bring back toward a robust burgundy instead of tossing them into a drawer, though with the one-to-one rate doing so does cost a premium. Many, however, seem undeterred by this: The store's yearly euro take exceeds 30,000.

"By the time you add the bank's commission and the hassle of waiting in line, converting euros back to dollars is not worth it," said a corporate lawyer for a large financial-services institution who visits Europe five times a year and is a frequent euro spender at the store (and who wished to remain anonymous). "And besides, if I don't use them here, I'll stash them away and forget where they are."

On a recent visit to East Village Wines, she had euros left over from a holiday to Greece. She decided to use the overage to fund the acquisition of two bottles of organic wine-a 2002 Bordeaux and a 1999 Cabernet Sauvignon from Washington State.

The blond thirtysomething, dressed in blue jeans, a black nylon coat trimmed with fur and a gray Cossack hat, carried her selections to the front of the store. After a few minutes of small talk with the friendly clerks, she placed a wrinkled E50 note on the Formica countertop.

"The total comes to $30.39, with tax," said co-owner Tom Chu, Bob's older brother, as he nonchalantly took the currency, bagged the bottles and handed over her change in U.S. dollars.

While most of East Village Wines' euro transactions go as smoothly, the Chus do see their share of hagglers. In fact, they recently set an unofficial $100 limit on purchases in an effort to deter customers inclined to protracted rate negotiations.

"They're not buying a house here," Bob Chu said. "It's only wine."

Accepting a wider range of currencies also increases the store's exposure to potential fraud. So far, however, only one person has attempted to pass a counterfeit euro note. The eagle-eyed Bob Chu spotted the forged E50, questioning its authenticity but deciding not to report the man to the authorities.

Not that the brothers Chu have any reason to worry. According to the U.S. Department of Treasury, East Village Wines' currency activities are perfectly legal. Foreign exchange-"FX," in the vernacular of Wall Street-is one of the least-regulated market activities, and there are no laws prohibiting a merchant from exchanging euros (or, for that matter, British pounds, Japanese yen or Mongolian tugriks). In terms of sales, "a retailer can accept paper clips for a good or service he provides, if he so chooses," said a Treasury spokesman.

Given the dollar's current status, paper clips might be an attractive alternative for Americans shopping overseas. For East Village Wines, the weak dollar has increased the frequency of euro transactions and the overall gross value of their euro-based take. "We've seen a bump in euro activity for sure," said Bob Chu. "But whatever we're making, we're giving back on the other end." Most of the store's suppliers are Europeans who demand to be paid in dollars, so import costs have increased by more than 25 percent since the dollar began its downward slide in the last quarter of 2004. In the currency game, sometimes a player cannot win for losing, no matter how a nice a guy he is.

-Peter Hyman

Not exactly.

As it turns out, the 34-year-old lawyer is one of a handful of Democratic candidates running in the crowded 2005 race for Manhattan Borough President, and the party was designed to raise money and build awareness with a constituency not known for its rabid interest in municipal affairs: the fashion industry.

Tapping friends in highly fashionable places and a fund-raising invite list that reads like a fall issue of Vogue, the candidate is hoping to make politics the new black, stitching together a politico-fashionista patchwork with the precision of a Prada loafer.

Mr. Ellner, an openly gay attorney who works in the litigation department of O'Melveny and Myers, is a true native son. He grew up in rent-stabilized Stuyvesant Town and attended public city schools before heading to the more private bastions of Dartmouth and Harvard Law. His entrée into politics came with an appointment to Community Board 5 in 1997. And like a miniaturized version of the Hollywood–Capitol Hill axis that Bill Clinton nurtured, Mr. Ellner has been utilizing the attraction that people feel for political power to create big-name alliances.

He now cites fashion P.R. powerhouse Ed Filipowksi and Peter Arnold, the executive director of the Council of Fashion Designers of America, as close advisors. And just as Richard Nixon turned to Henry Kissinger on matters of foreign policy, Mr. Ellner has Jeffrey Kalinsky, the owner of Jeffrey New York, for equally crucial guidance.

"The political part is not my forte," said Mr. Kalinsky, who has offered to help Mr. Ellner with wardrobe refinements. "But Brian looks every bit the part of a U.S. Senator in training. He almost evokes a modern-day Kennedy."

Like J.F.K., Mr. Ellner is a charismatic and debonair liberal. And, given the sartorial limits of civil servitude, where a gray Brooks Brothers sack suit is considered chic, being well put together is certainly a differentiator. Still, it's hard to see what style has to do with making sure the borough's garbage gets collected.

But while Mr. Ellner may be overdressed and inexperienced relative to the rest of the field of career politicians vying for the Beep's office-his highest elected position was the presidency of the District 2 School Board, though he did work briefly for former Public Advocate Mark Green-he is passionate about issues ranging from civil rights (he supports the legalization of same-sex marriage) to affordable housing (he fears Manhattan may soon become an "outdoor mall for millionaires").

And despite an affinity for what Mr. Kalinsky calls "modern classic" suits, the dapper candidate claims to be a fashion novice, more interested in his weekly pick-up basketball game than this season's couture collections. Whether this is true or simply a man-of-the-people pose, his boyfriend Simon Holloway, a senior design director of the women's collection at Ralph Lauren, brings a closetful of insider influence to the endeavor.

"Before I met Simon, I didn't know the difference between a Manolo and a Mombasa," said Mr. Ellner. In addition to teaching his boyfriend to distinguish iconic Italian footwear from rare Yves Saint Laurent handbags, Mr. Holloway provides a crucial point of entry into the city's fashion elite.

These connections have helped attract A-list star power to the campaign, including Diane von Furstenberg and culture czarina Ingrid Sischy. The two will host an "Ellner for Manhattan" fash bash for 600 guests at Ms. von Furstenburg's meatpacking district studio in late March. And on March 13, some supporters are throwing a fund-raiser at the salon of Sally Hershberger, the style impresario known for her $600 haircuts and $1,000 jeans. Tim Gunn of Project Runway is also a supporter.

Whether the constituency that can spot a DVF wrap dress and reads Interview magazine will trudge out to vote on primary day remains to be seen, but they have been generous with their pocketbooks.

According to the New York City Campaign Finance Board, as of Jan. 18, 2005 (the last legal filing deadline), Mr. Ellner had raised just under $170,000. Among the more fashionable names on his donor list are downtown darling Zac Posen; Mark Lee, the newly installed president of Gucci; designer Lela Rose, a red-blooded Texan who, ironically, has created several outfits worn by First Daughters Barbara and Jenna Bush; and Project Runway star Tim Gunn, the fashion director of the Parsons School of Design.

With New York City's public matching-funds program, this figure could translate into almost $500,000. By law, candidates for Borough President can only spend $1.289 million. Mr. Ellner has some work to do, but he's off to a robust start. This is partially due to his aggressiveness at throwing fund-raisers, most of which have had a distinctly fabulous feel.

High fashion and politics are not the strangest of bedfellows. But while P. Diddy encouraged citizens to "Vote or Die" and designer Marc Jacobs donated his talents to Downtown for Democracy, they were canvassing on the national stage. Mr. Ellner's fashion partnership is unique at the local level, where fixing potholes is often the most glamorous item on the agenda.

"Historically, fashion people have not been at the front lines of politics in New York City," said Mitchell Moss, a professor of urban policy and planning at New York University's Wagner School. The irony is that the city's apparel industry generates nearly $35 billion in revenues annually and employs 150,000 people, making it a sector well worth embracing.

And in New York City, where participation in municipal elections hovers at about 25 percent of registered voters, enlisting new voters can tip the scales. Moreover, because the Manhattan Borough Presidency is often decided by a crowded Democratic primary and not a general election, a candidate can win with a relatively small percentage of the vote. For Mr. Ellner, victory could mean a critical mass of as few as 35,000 well-dressed supporters who pull his lever on primary day.

There are, however, risks involved with relying on the ultra-fashionable as a base of support.

"I've never voted for Borough President, and I'm not proud of that," said Michelle Giuliano, an executive at Burberry. She did reveal her own rationale for why tapping the fashion crowd made political sense: "We may not be curing cancer, but we are some of the most fun people in the city. And we look fabulous."

This latter fact was evident at the recent holiday-themed Ellner fund-raiser hosted by Kevin Carrigan, the creative director of CK and Calvin Klein.

"I admire the causes Brian is fighting for," said Mr. Carrigan, "even though I cannot actually vote for him." Mr. Carrigan is British, so he showed his support by donating the use of his sprawling Chelsea loft, a modernist's paradise awash in earthy hues and mid-century furnishings.

Some of the guests who were eligible to vote shared Mr. Carrigan's admiration for Mr. Ellner, even if they didn't understand the specific nuances of the office for which he's campaigning.

"It sounds as if [Borough Presidents] follow up on agendas and make sure promises are being kept," said Beth Mayer, a vice president of merchandising at Ellen Tracy. A born-and-bred Republican, Ms. Mayer confessed that she was planning to cross party lines to vote for Mr. Ellner. However, as election laws would have it, only registered Democrats can participate in the Democratic primary.

Michael Giannelli, a vice president of design at the Gap, was more vocal about his uncertainty. "Borough President? What is that?" said Mr. Giannelli, who matched a chocolate-brown velvet Paul Smith blazer with Adriano Goldschmied jeans. "Do they go to fashion shows?"

According to the office of current Manhattan Borough President, C. Virginia Fields, the role has more to do with serving as an advocate for the needs of Manhattan and its more than 1.5 million residents than it does with mingling under the white tents of Bryant Park, though the semi-annual shows do fall within the Borough President's geographic purview.

Despite the confusion of some of his supporters regarding the office he seeks, Mr. Ellner is outspoken, especially on the one issue that promises to dominate the 2005 citywide elections: the proposed $1.4 billion football stadium for the New York Jets on the West Side of Manhattan. As it turns out, so are several of his fashion-world supporters.

"I know I'm a lone wolf on this, but I think the stadium would be good for urban renewal," said Mr. Giannelli, between servings of mulled wine at the Carrigan affair. "I mean, just picture Madonna under a retractable roof. It's breathtaking!"

Mr. Ellner, an avid Jets fan, disagreed, citing quality-of-life issues and more beneficial possible uses for the funds, such as education and keeping Manhattan safe. "The Jets played in Flushing, Queens, when I was young," said Mr. Ellner, who was also dressed in a dark velvet blazer and jeans. "I am more than happy to take the 7 train to home games." But if his fashionable friends come through next September, Mr. Ellner's attentions may soon be focused on the borough due west of Queens.

A decade ago, I was a 25-year-old magazine staffer trying to navigate the seemingly glamorous world of Condé Nast Publications. Being set adrift in such an expansive sea of well-tailored talent should have provided a rich vein of dating potential for a straight single man. Yet I was stunningly unsuccessful in my efforts, fumbling about like some minor P.G. Wodehouse character reincarnated as a twentysomething publishing hack with Internet access and a gym membership.

My work-related inadequacies thus forced me to fend for my romantic life at book parties, gallery openings and any other velvet-roped events I managed to doubletalk my way into. At one such affair, I met a captivating redhead who, as an added bonus, was a media bigwig with much to offer in the way of career advice. Ruth was fit and fantastic-looking; to stand next to her, you never would've known that she was 49 years old-a fact that eluded me when we met. Looking back, her lengthy digressions about Studio 54 and Patti Hearst should have stopped me cold. But as so often happens when copious amounts of complimentary off-brand vodka are involved, the night fell into a passionate state of affairs, leaving me no time to check her paperwork.

I soon began to enjoy the fact that she was older. Ruth had a wealth of life experience, and she brought this wisdom into the relationship. She was nurturing, warm and too out of touch with popular culture to realize that my "conversations" were simply recycled episodes of Seinfeld. And she did not impose the artifice of commitment. There were no demands for daily phone calls, or inquiries as to what our future together might look like. Ruth was able to date just for the moment-not the norm with women my own age. This independence was liberating, and my commitment to her grew out of respect, not a request on her part.

But more than anything, Ruth fell squarely into the wheel house of the female "sexual prime." Like a well-rehearsed orchestra, Ruth's talents had blossomed with years of practice; she was playing with the sophistication of the Vienna Philharmonic. And, unlike younger women I had dated, Ruth had few inhibitions. I recall several public romps in various museums that were likely jailworthy under the iron hand of Giuliani's "decency" laws.

And Ruth's emotional openness stood in striking contrast to my youthful detachment. Her willingness to discuss her broken marriage and career failings taught me how to open up and communicate-not a skill I had in surplus at that aloof age. By leaving herself so exposed, she showed me the difference between vulnerability and insecurity.

In fact, things were going very well-until the night we accidentally bumped into Zoe, her stunning, midriff-baring 24-year-old daughter. Men face enough romantic challenges as it is; the desire to sleep with your girlfriend's youngest child is an extra hurdle we don't need. But with her blue eyes and bohemian-chic outlook, Zoe was exactly the sort of woman I imagined myself settling down with. And here I was, dating her mother. If I ever had a chance with Zoe, this reality reduced the odds substantially (as did the fact that she was happily involved with a well-known artist).

Ruth was concerned that her daughter might not approve of our affair, so we were forced to create an elaborate ruse: I became Ruth's private yoga instructor, offering personal tutorials in exchange for media-world advice. That most Three's Company plots are rooted in better logic seemed unimportant to Ruth as she explained all of this to Zoe over a late meal at the Corner Bistro. Our explanation, in fact, raised more questions than it answered. Why, for example, was her mother out with her "yoga instructor" past midnight on a Tuesday? Why was a man so devoted to clean living ingesting red meat and Scotch with the fervor of an underfed Teamster?

The difference in our age became glaring when we socialized with friends. I grew to resent spending every Friday night at stuffy dinner parties discussing the escalating cost of Ivy League tuitions-especially when my most pressing economic concerns involved securing funds for upcoming Pavement concerts. And while Ruth never said anything, I don't think she felt comfortable with my gang, for whom "home décor" meant replacing our post-collegiate milk crates with equally unattractive unfinished wooden bookshelves. Making plans became an exercise in choosing between the gentrified bohemia of the East Village and an evening of canapés on Park Avenue. Neither of us fit neatly into the other's real life, despite our efforts to fake it.

The clincher came during a brunch I rashly set up with my parents during one of their spur-of-the moment weekend visits. I had told them I was dating someone, but did not provide any significant details. My folks are intelligent people, but they came of age in an era when courtship was a simple, expedient enterprise. They have never been exposed to the limitless romantic potential-or neurotic overanalysis-that accompanies modern dating. I usually operate under a strict "don't ask, don't tell" policy.

Yet there I stood, one sunny Saturday morning, introducing them to my "chatty older ladyfriend," as my mother would come to refer to her. While my father's sidelong glances indicated a mild sense of confusion, Ruth and my mother hit it off, beginning a long discussion about the flea markets below 26th Street. And as fate would have it, they were both devotees of Murder, She Wrote. As they professed their mutual admiration of Angela Lansbury, a critical recognition dawned on me: Ruth and my mother were contemporaries. It suddenly felt as if I were dating my aunt, not a sultry divorcée with an account at La Perla.

As it turned out, Ruth was feeling the same way, which made the eventual breakup easier. Though I missed her for many months thereafter, it was time for me to get back to being turned down by women from my own generation. She is nearly 60 today, and probably a grandmother, which makes any sort of fallback far too weird for me to even consider. Not that I'd really want to. I'm now dating (at least until she reads this essay) a perfectly youthful 32-year-old, and she is the beneficiary of what I learned from Ruth: that older women are often self-aware and deeply sensual, but differences in age present some quirky, perhaps insurmountable obstacles. What's perhaps more important, though, is that Ruth opened my eyes to the possibility of a partner who has both the limitless enthusiasm of youth and the level-headed steadiness of maturity. So here's to you, Mrs. Robinson.

Peter Hyman's first book, The Reluctant Metrosexual: Dispatches from an Almost Hip Life, was published in August by Villard.

I discovered this as I walked into the small, dimly lit massage room, where I met Hans, a tall, well-built fortysomething who looked as if he owned a pair of leather chaps for weekend use. No problem, I thought, trying to keep positive. Hans seemed nice enough, and when he lit the candles and started the Enya CD (does the massage guild require all members to use the same music?), I began to drift off into that semi-relaxed massage-induced state.

Massage therapy, once an indulgence of the country-club set, has become the Starbucks of the bodywork world. An estimated 35 million Americans spend roughly $3 billion annually on visits to massage practitioners, totaling 75 million visits each year. For me, it's become the equivalent of air travel or medical exams: I rely on it, but I tend to want the procedure to be over relatively quickly, and I can't be bothered with idle conversation. Hans, however, was unnaturally talkative for a man whose livelihood involved rubbing naked flesh. I did my best to ignore him, but the questions kept coming. "What do you do for a living?" "Do you stretch after you exercise?" "Do you know how tight your abductors are?"

I mumbled responses-I'm a writer and a comedian, usually; I didn't know I had abductors-hoping my terseness would put a damper on his curiosity. It didn't, and he continued chatting as he kneaded his way up my thighs, his fingers dancing dangerously close to the unauthorized no man's land. I was put more at ease when he moved to my shoulders, safely away from the more vulnerable territories to the south. Eventually he asked me to turn over.

The flip-over is always tricky, particularly when all that separates you from full exposure is a rag the size of a postcard. But through a mix of dexterity and towel origami, I was able to make the turn relatively smoothly. Now Hans was working on my front side, so he was able to speak directly to me. I could no longer pretend I couldn't hear him. I was vulnerable, and Hans seemed to sense this.

"So, have you ever modeled?" Hans casually inquired, rubbing my chest.

"Uh, no," I said, pausing. "Not really." Not really? Why my response left open the possibility that, yes, I did do backup work on the occasional Tommy Hilfiger print campaign, I'm not sure.

"Oh. Well, you should think about it," Hans replied.

"Yeah, um, I'll look into that," I said, wondering aloud whether freelance day work would disqualify me from collecting unemployment benefits.

And so it was that I learned an important rule of massage: Never discuss your recent layoff, unless you actually want career advice from a man rubbing warm Juniper oil into your midsection. After a mumbled response from Hans and a moment of uncomfortable silence, things seemed back on track, and he moved down to my quads. He then announced that he would move on to my head and neck. Fine, I thought, closing my eyes.

The next question knocked me off-balance again. "Would you care for a release?" Hans asked matter-of-factly.

"Um, I'm not sure. What is that?" I stammered, hoping that the "release" was an ancient method by which he was going to balance my chakra or realign my negative energy.

"Well, some clients like to be masturbated as a part of their massage," Hans answered, as calmly as if he were reading aloud from the box scores of a meaningless midseason Yankees-Tigers game.

"Masturbated-huh." It had been a tough season with the ladies, to be sure. But even so, I was not prepared to move to this level.

"Yes, masturbated," Hans said. "Does that interest you?"

"Um, yeah, not so much," I said. "But thanks for the offer, I think."

Undaunted by my refusal, Hans continued on as though nothing had happened. But my mind was racing. Had I done something to inspire this offer, or was it simply part of the normal package given to all male clients (like some perverse form of free underbody rust-coating)? Had he broken the law? And was I now obligated to give him a bigger tip? I was confused, and suddenly not at all relaxed.

The massage went on for another 10 minutes. When it was over, I walked out quickly, thanking Hans under my breath. I took a long shower and considered my options. I could complain to the management, demand my money back and, possibly, score some gym-based perks as payment for my trauma (free Cliff Bars for life?). But then Hans might be fired or disgraced professionally. That seemed too harsh. I chose not to say anything.

When I got home, I checked out the Web site of the National Certification Board for Therapeutic Massage and Bodywork (NCBTMB), a not-for-profit whose mission is to "foster high standards of ethical and professional practice for therapeutic massage and bodywork professionals." My research yielded no mention of the "release" as a current standard or recommended procedure. Hans, it seemed, was working off the books.

And while the "release" or "happy ending" is quite common in certain corners of the massage world (Asian parlors are particularly famous for it), one doesn't generally expect it at an upscale Manhattan establishment. Perhaps, as massage therapy goes mainstream, it's simply harder for the agencies charged with governing its practices to keep a watchful eye.

In the end, Hans' offer felt presumptuous and objectifying-but I also know that that's slightly disingenuous because, had it been a cute woman, I would have faced a tough choice. And in fairness to Hans, I should admit that I fall into the "straight but gayish" camp: men who, while sure about our heterosexuality, gravitate toward mid-century modern design, opera and flat-front trousers. That we even use the term "flat-front trousers" is evidence of the sexual-orientation vagueness we seem to emit. A bit of unwanted male attention is the price we pay for being just gay enough. So, while Hans' offer was flattering, it left me wanting to swaddle myself in pleated Dockers while guzzling pitchers of warm Schlitz in a sports bar.

I still belong to the gym, and I still see Hans, hovering in the doorway of the massage room. We don't make eye contact, though I think I can feel his cold glare. It's my allegiance to the gym that forces me to deal with our awkward situation-a release-crazy massage guru and a former client weathering the uncomfortable silences of a not-so-happy ending.