Adam Horovitz, a.k.a. Ad-Rock.

Last Friday, one year to the day after the death of the Beastie Boys’ Adam “MCA” Yauch, the Transom stood at the far west end of Atlantic Avenue, in a small but familiar neighborhood park in the shadow of the BQE, for a dedication ceremony in which Palmetto Playground would be renamed Adam Yauch Park.

This was where the Brooklyn-born rapper/director/humanitarian, who grew up blocks away on State Street, learned to ride a bike, and where he played hoops—on the very same court where the Transom plays pickup every Saturday with guys like Jim Strouse. Mr. Strouse, an independent filmmaker, also in attendance, may well spend more time at this little slice of asphalt than anyone else in the borough.

The crowd of about 250 fidgeted in the midday sun. Gen Xers climbed aboard a nearby jungle gym—for the first time in decades, one imagines—to secure a better view as the guests of honor, fellow Beastie Adam “Ad-Rock” Horovitz and Mr. Yauch’s parents, Noel and Frances Yauch, took their seats.

Arthur Dobelis, the founder and CEO of tech startup Evivio and another pickup regular, turned to Mr. Strouse. “It is kind of your park,” he said.

“Who just said that?” asked Adrian Sas, a local TV producer who works for a show called It’s My Park, which airs on channel 25.

“It’s not really my park,” Mr. Strouse said. And the Transom agreed, since we defeat him so regularly at one-on-one.

“I wish I were filming this,” Ms. Sas said.

Flashbulbs popped and recorders rolled moments later as Brooklyn Borough President Marty Markowitz, Ad-Rock and Frances Yauch, among others, gave remarks. Mr. Markowitz ended on a purposefully goofy reappropriation of a Beastie Boys lyric. Ms. Yauch remembered how much noise the fledgling rap trio would make rehearsing on the top floor of their home. “God bless our neighbors who never complained,” she recalled.

Longtime Beastie Boys manager John Silva, who also spoke at the ceremony, told the Transom later about the group’s forthcoming memoir, which will reportedly hit bookshelves in 2015. “It’s so early on,” he said, standing alongside his wife. “My help so far has been to gather my ridiculously extensive archives and have all that available to Sacha [Jenkins],” who will edit the book.

Mr. Silva’s wife sighed, “The good news and the bad news is he’s a pack rat.”

“And the band never really threw anything away,” he added. “It’s going to be great.”

Which is when Moneyball producer Rachael Horovitz, Ad-Rock’s sister and a driving force behind the park dedication, burst into the conversation. “Everyone keeps saying that it’s going to be the most stolen park sign,” she said, sounding both amused and concerned.

Mr. Silva considered this. “The money you and I will have to raise every year just to buy new signs,” he said.

On the other side of the park, a scrum had formed around Mr. Horovitz, who hid behind a pair of black wayfarers with pink temples, and Mr. Yauch’s family members. Mr. Horovitz admitted that he had been hoping to shoot some hoops today—that his brother had even brought a basketball—but there were too many people here for that to happen.

As Mr. Horovitz moved toward the exit, the Transom caught his attention and told him that we play here every weekend and would, in fact, be playing the next day.

“Oh, yeah?” he said, stopping to talk, peering over the top of his sunglasses. “What time?”

And we told him.

But not before Ms. Sas forced her way to the front of the scrum and demanded to know: “Whose park is this?”

Ad-Rock’s response—the only adequate response: “This is Adam Yauch’s park.”

Amar'e Stoudemire.

When Amar’e Stoudemire took the stage after the screening of his new documentary, In The Moment, last Thursday night at Marquee, he genuinely seemed to appreciate the attention and applause that greeted him from the packed house of athletes, musicians, fashion designers and more than a few men in yarmulkes.

It was less than 24 hours after the New York Knicks had closed out their best regular season in 16 years (having captured the Atlantic Division crown and the Eastern Conference’s No. 2 seed), and a near-starting lineup, including Carmelo Anthony, Tyson Chandler, Iman Shumpert and Chris Copeland, had turned out to fete their oft-injured teammate—a rare bright spot in what has been yet another snake-bitten season for Mr. Stoudemire.

Not that he looked particularly unhealthy on this night. Mr. Stoudemire was red-carpet sharp in a fitted black sport coat, a camouflage bow tie and some sort of gold boutonnière—an ensemble he might have the chance to reprise in the coming weeks. (His latest setback, a knee debridement, has all but ensured that the six-time All Star will miss the team’s first-round matchup against the Boston Celtics.)

“Oh, we’re definitely going to get out of the first round,” Mr. Stoudemire said in a conversation with Stephen A. Smith following the film, which gives fans an intimate look at both his troubled family history—his father, Hazell, died when he was 12; his mother, Carrie, spent years in and out of prison; his older brother, Hazell Jr., was killed in a car wreck last year—and the former first-round pick’s journey from impoverished high school prodigy to Rookie of the Year to New York Knicks savior.

And lest fans forget—as many seem to have—that’s exactly what he was, signing with the organization in 2010 when other superstars, like LeBron James, snubbed the city’s bright lights for Miami’s sun-stroked beaches.

“I wanted to accept the challenge and revitalize a team that needed help,” Mr. Stoudemire recalled.

In his first season with the Knicks, the man known as “STAT” set a franchise mark with nine consecutive 30-point games while leading the team to its best start since the 1996-1997 season. He earned “M-V-P” chants from the Garden faithful. Vogue put him on its cover and called him a “basketball deity.” The New York Post wrote, “Carrie Stoudemire has given birth to New York’s basketball messiah.” (In the documentary, Ms. Stoudemire admits to having tried to abort her “billion-dollar baby.”)

Still, the high-flying forward was not immortal. Mr. Stoudemire matched a career high in minutes per game that first season, as then-Knicks head coach Mike D’Antoni demanded too much of the team’s fragile new superstar—a player whose contract was literally uninsurable. (Coach D’Antoni has come under similar criticism this season for overtaxing Lakers star Kobe Bryant, who recently ruptured his Achilles tendon.)

By the time the Knicks shipped nearly half their roster to Denver in exchange for Carmelo Anthony, the team was relevant again, but the minutes had added up. Injuries returned, and the spotlight instantly shifted from Amar’e to Melo.

Last May, when Mr. Stoudemire injured himself for the second straight postseason, the goodwill was all but gone. ESPN New York columnist Ian O’Connor wrote of Mr. Stoudemire, “He should be thanked for the pre-Melo memories, and sent on his way.” And in the months that followed, the Knicks reportedly shopped him to every team in the league, making him “available for free.”

The business of sports can of course be heartless, but such treatment seemed especially cold. This, after all, was the man who signed with the Knicks when no one else would, who once again validated New York as a destination for star players after so many failed arrivals, who gave his heart and soul—and yes, his knees—to a city so that its team could thrive.

And thrive it has ... even without him. Carmelo Anthony is playing MVP-caliber basketball, and the Knicks are poised for their first legitimate playoff run since 2000. But Mr. Stoudemire is not bitter. He continues to train hard. When healthy, he has embraced a role off the bench (his style of play and Melo’s were never meant to mesh). And unlike the city whose team he saved, he remains grateful—because he remembers what those lean years growing up were like.

“The thanks is always there,” he said. “Even if you’re in hard times, as I am now with the injury, I still give thanks. And it helps. What food is to the body, prayer is to the soul.”

And as a Knicks fan who remembers those lean years of Isiah Thomas and Stephon Marbury, the Transom says: amen.

Kimani Gray.

Walking east along Church Avenue from Nostrand last Thursday afternoon, The Observer counted two police officers on every corner. At New York Avenue, there were five cops and two squad cars. From a row house just past East 35th Street, three men in bulletproof vests and black topcoats emerged. And once we reached Albany Avenue and saw the Police Department’s outsized Communications Division Command Post vehicle, we stopped counting.

“We’re kind of used to it,” one man told The Observer. “In neighborhoods like this, there are always cops around. It’s just more now.”

More, of course, because of the controversial killing of 16-year-old local Kimani Gray, who was shot seven times late the previous Saturday night by two plainclothes officers after allegedly drawing a weapon, and because of the subsequent nights of demonstrations, which resulted in instances of looting and dozens of arrests.

“It was terrible last night—the crowd, the stone throwing. I haven’t seen anything like this,” said Junior Harrison, owner of Island Pride restaurant. “I thought it was L.A. for one minute. It’s getting worse every day.”

Mr. Harrison remembered Mr. Gray as “nice kid” from the neighborhood. “All the kids around here, they always eat here,” he said, standing outside of his store near East 54th Street, less than a block from the vigil site. “The same day he passed away, he had his meal here. I’m going to miss him. He’s a good kid, from my point of view.”

Near where he was shot, a poster hanging in the window of a hardware store called for an independent investigation into the shooting. Inside, there were three men sitting on overturned paint buckets. Asked about the incident, the man in the middle took off his Twin Towers ball cap, scratched at his skull and said, “I don’t know what you’re talking about. I have nothing to tell you.”

A variety of media reports have blamed outside agitators for stirring up the community’s emotions. While there were a variety of non-locals at the scene of the vigil even when The Observer visited it, at 4 p.m. on Thursday, it was clear that the community’s emotions were real.

“You can’t just take a life!” said the proprietor of an event hall called Extreme Elegance, who declined to give his full name, as we walked with him back down Church Avenue.

“Right now, if I have a problem with you, I wouldn’t call the police,” he continued. “People come inside here and rob me, and I would never call the police. Never!”

“Eleven shots!” chimed in Kevon Julian.

“He got hit seven times, but they shot at him 11. These kids, they’re terrible. But they get older. To me, they targeted him. Out of the crowd, they see him. They know what he’s about, and they said he had something, but he really didn’t have anything that day.”

A group of young teens stood staring at the posters around the neighborhood, which held grieving testimonials to Mr. Gray’s short life, until one said, “I’m out, son. I can’t see this kid anymore,” while two reporters shoved mics into another young resident’s face and grilled him about Mr. Gray.

“He used to do a lot of bad stuff,” the subject said.

“Were you afraid of him?” one of the reporters asked.

“No.”

Community organizer Shamar Thomas, who rose to YouTube fame with his video “1 Marine vs. 30 Cops,” in which he beseeches police officers to stop physically harming members of the Occupy movement, implored others to be constructive.

“We have to channel the anger,” the Brooklyn resident said. “Everyone is out here egging it on. But going to jail, messing with the cops that are right here. These ain’t the killer cops. We yelling at the regular motherfuckers that are on the street. Organizing is our only weapon. Unity is our threat.”

And then, on cue, Mr. Thomas broke away to calm down a middle-aged man who was not a local and was getting himself very riled up.

“They cornered us into a little group,” the man said, reliving the previous night’s demonstrations. “It was like hundreds of us on top of each other, the way they locked us down. You couldn’t breathe ... Then they started arresting the young ones. They threw me against the wall a few times. I didn’t understand. Grown-ups were getting thrown against the wall and they wasn’t getting locked up.”

Ostensibly all these demonstrations were for Kimani Gray—whom one resident described as “a hood star”—but they were rooted in long-standing tensions between residents and police. Many at the scene of the vigil were wearing anti-stop-and-frisk buttons.

“I don’t like how cops pull over black males for no reason. They don’t stop—no disrespect—white males. And then when kids die, people think it’s not a big deal,” said 13-year-old Iziah McPhatter, who hails from Downtown Brooklyn but was here with his twin brother and his father, a former Bloods gang member who founded an organization called Gangstas Making Astronomical Community Changes, or GMACC.

According to Mr. Harrison, it’s important for the community to have some closure. “They know what they’re mad about—it’s about the shooting,” he said, before adding, almost rhetorically: “Where do we go from here?”

Lena Dunham at the Purim Ball.

Turns out there are at least two people in New York who don’t know who Lena Dunham is.

“Who was that girl with the two house tattoos on her back?” a couple of security guards asked the Transom as we walked into the Jewish Museum’s Purim Ball at the Park Avenue Armory last week. “The one everyone was making a big deal over?”

That, we informed our basic-cable-watching friends, was Ms. Dunham, the evening’s official Purimspieler and something of a main attraction. “Who?” they said again.

But she wasn’t the only gal with ink in the house. As we meandered alongside another tatted-up Jewess during the evening’s cocktail hour—which, like most of the event, had a distinct bar mitzvah-party feel—we overheard an old bearded dude getting a little judge-y: “Since when do Jews have tattoos?” he said.

But really, weren’t we all here to get along? From men in floral-print suits to at least one middle-aged vixen in an approximated Miss America costume, it was all kosher. Others in attendance had glitter tattoos, but we suspected those weren’t permanent.

When cocktail hour finally gave way to a seated dinner, the Transom found ourselves at a table of artists, most of whom were pals of Claudia Gould, the Jewish Museum’s director, although only some of them understood the holiday properly. So we explained, as rabbis have done for generations: Purim is that time of year when Brooklyn assemblymen learn the true meaning of racism.

To our left, Martha Rosler was very much in the Purim spirit. “Look at me,” she said, shaking her shoulders in some sort of seated dance, outfitted in a black-and-gold paisley blazer and Mardi Gras beads. “I’m wearing ridiculous things.”

On to dinner, and Ms. Dunham, as the Girls star/creator took center stage in front of the nearly 1,000 attendees, welcoming everyone to her bat mitzvah (we told you-—such was the vibe). As official Purimspieler, Ms. Dunham regaled us with the tale of Queen Esther and the Persians, all the while maintaining the speech patterns of Eloise, that children’s lit protagonist who lives on the “tippy-top” of the Plaza Hotel. “He picked Esther,” Ms. Dunham spieled, referring to the Persian king. “She was an orphan, which is pretty much the coolest thing you can be, like Pippi Longstocking or Drew Barrymore.”

With the story thus told, schmoozing took hold, and conversations naturally turned to Ms. Dunham’s breakout HBO show. Filmmaker Joe Lovett informed us he had just seen the first episode and that it was “very well done,” while some bleached blonde in a black dress had a harder time forming her opinion.

“I saw the first season and it was, like, really quite funny,” she said, “but, like, the second season? Like, I don’t know. I saw it.”

She then either stopped talking or our head exploded. It was now mercifully time to hit the dance floor. And it was just like they say in that old hip-hop ditty, which goes a little something like this:

“After Purim is the after party. After the party is (two hours of awkward middle school-grade grinding and groping just a hundred feet or so from) the Park Avenue Armory lobby.”

We just hope that, by the end of the night, someone became a man.

“Well, I hope so,” Logan says, making himself comfortable.

I hand my guest a glass of bourbon, join him on the sofa. This is not a date. Logan has just worked another 12-hour shift at the Brooklyn hospital where he is finishing out the clinical rotations of his fourth and final year of medical school—though he looks no worse for wear: bright eyes, knit tie, khakis.

Perhaps to make up for my lack of nudity, Logan begins scrolling through his iPhone, showing me samples of the naked photographs and pornographic videos he has received from literally hundreds of women. Logan pauses on a topless photograph of an attractive 20-something. He has slept with this person.

“One problem with her,” he sighs. “Bacterial vaginosis. It’s the only one that smells uniquely fishy. And hers was uniquely fishy.”

As he is a doctor-to-be, and not an unattractive guy by any means (with a face some might call “boyish”), it should come as no surprise that Logan, at age 30, is a lady-killer. Really, he’s a Jewish mother’s wet dream. And over the past year and a half, there’s a decent chance that Logan has slept with that Jewish mother as he perfects the craft of conning women of all colors and creeds between the sheets.

“It makes sense to me, as a science guy,” Logan explains. “Your goal evolutionarily is to spill your seed in as many women as possible. As soon as you’re done, your job is to move on.”

Logan’s real name is not Logan, of course. But Logan is the name that he provides to women when he meets them online, on websites like PlentyofFish and Seeking-Arrangement—the dating service famous for connecting “sugar daddies” and “sugar babies.” Whatever else he tells them depends on his perception of what each woman needs to hear to part with her underpants. And more often than not, that means playing up a perceived socioeconomic power difference, with the implied—and sometimes explicit—promise of money and comfort to come. As he puts it, “Most of the girls I go out with expect it to be something of a sugar baby-sugar daddy relationship.”

Logan wasn’t always a sexual assassin. Growing up in a sleepy East Coast suburb, he attended Jewish day school and didn’t fool around with a girl until 10th grade, the first of his friends to do so. With no one to discuss the experience with, Logan grew confused and retreated into his religion, becoming shomer negiah, meaning he wouldn’t even shake the hand of anyone of the opposite sex (immediate family excluded) and wouldn’t have another sexual experience until marriage. He held fast throughout the rest of high school and all of college, throughout a year studying in Israel and another year abroad. He didn’t get a handshake from a woman until age 23, a hand job until 24, finally giving up the ghost of his virginity at 26 and making up for lost time ever since.

At first, Logan went the traditional route, looking for love via setups and JDate. But he never seemed to make a real connection. “None of these girls liked me. Every time, I was shocked,” he says. Then, after his first two years of medical school, Logan decided to try a different tack. He signed up for a series of new sites, all under his new name. (“I don’t know why anyone would give their real name,” he says.)

The platform he first focused his attention on was PlentyofFish, a free dating website. Right away, he noticed a difference. Presenting himself as a man of means, Logan’s inbox filled with communications from willing women. Did this new power dynamic make a difference? “Of course,” he says. “That’s what makes it so easy. Plus, they actually really appreciated a professional guy. Whereas the Jewish girls I’d gone out with, they couldn’t care less. So No. 1, it’s nice to talk to these girls because they have that look in their eye, they admire what you’re doing. And No. 2, it’s much easier to bang them on the first date.”

With that lesson learned, Logan soon decided to check out another website, the literal pay-for-play SeekingArrangement, buying a one-month introductory membership.

He put down his name: Logan.

Profession: web entrepreneur.

Net worth: $3 to $5 million.

Over the course of that month, Logan contacted as many women on the site as possible—a number he estimates to be between 300 and 500—and then steered those conversations to an alternate email account. That way, when his month was up, he could get to work.

“I just started going through their contact information like a menu,” he says. “What am I in the mood for tonight? Ethnicity-wise, it was like a Benetton commercial. Which was nice. I enjoy some variety.”

Pretty soon naked pictures were flooding his inbox, as prospective sugar babies vied for Logan’s attention—and his fake bank account. Were they all reckless fools? Maybe. But to his credit, Logan was a convincing character.

“I think the easiest way to lie is to replace as little of your life story as possible. That’s what I’ve embraced. So the only thing I’ve replaced was the three years I was doing medical research has become three years investing in startups in Silicon Valley.”

Logan’s fabricated back story hinges on a seed accelerator known as Y Combinator, which has helped produce such companies as Reddit, Dropbox and Airbnb. “I tell them I had some bar mitzvah money that I decided to invest, and that’s how it got started,” Logan tells me. “So I invested $10,000, and it doubled, doubled again, doubled again. I don’t give figures, but I say I was kind of able to retire from that life and start medical school.”

And in that way, he brings the story full circle. “It’s just easier that way,” he says. “I don’t have to make up new stories, which would be too much stress. And they like that, also: ‘He’s a rich entrepreneur and he’s a doctor.’”

Logan pauses for a moment to contort his voice into the stereotypical Jewish mother’s: “So ambitious,” he says.

Though the idea of lying over the Internet is as old as the dial-up modem, it’s having a modern media moment, thanks in large part to star college football player Manti Te’o. Recently, Mr. Te’o found himself the victim of a nationally publicized hoax, after falling in love with a “woman” he met online and then telling the world that she had passed away, garnering sympathy in the lead-up to the Heisman Trophy presentation, for which he was a finalist.

Turned out she wasn’t dead—or alive, for that matter. She simply wasn’t.

This practice is known as catfishing, a term that can be traced back to the 2010 film Catfish, which follows NYC resident Nev Schulman as he builds an online relationship with a Midwestern woman. When Mr. Schulman begins to suspect his sweetie isn’t who she says she is, the filmmakers follow him halfway across the country for an in-person confrontation.

When I spoke with Brandon Wade, founder and CEO of SeekingArrangement, he said he was all too aware of catfishing. “We’ve actually kicked off a lot of people over the years who pretend to be, say, rich when they’re not in fact rich,” he told me. To combat this, the dating site offers safety features, such as background checks, which members can use to secure verified profiles. But ultimately, Mr. Wade admitted, the responsibility to protect oneself resides with the user. “Short of verifying everybody’s Social Security number, I mean, short of that, there’s just no way of preventing such lies from happening.”

As if to prove Mr. Wade’s point, Logan got a chance to test his SeekingArrangement fibs in the real world last February, when he arranged to meet a sugar baby—whom we will call S.—at a beer-and-wine bar just off Smith Street in Brooklyn. Logan prepared for the date by doing the same thing he’s been doing for years at medical school and at yeshiva: research. He memorized the names of various tech CEOs and all the companies they dealt with. He double-checked his time line, made sure the dates lined up correctly. “You don’t want to walk into the bathroom in the middle of a date and have them Googling all this stuff and realizing I’m full of shit,” he explains.

Still, Logan was nervous.

Logan and S. had exchanged emails but had yet to talk on the phone. What he knew about her: she was Irish, by way of Australia. She was a nutritionist and a belly dance teacher. She had a killer body. “I was a little nervous to be asked some difficult questions,” he says. “But they want to believe it. The second I brought up money, she had both hands on my thigh.”

Confidence rising, Logan suggested they go somewhere more private, and she agreed, thinking they’d be heading to his “expansive condo overlooking the Gowanus Canal.” Alas, his place was being fumigated, so they walked to her rented room. On the way, the subject of a monthly allowance came up. While S. said she was accustomed to receiving $5,000 to $10,000 a month from her sugar daddies, Logan suggested they start off at $1,000, and she jumped on it. “I thought to myself, what would an actual sugar daddy do?” Logan says. “An actual sugar daddy would try to negotiate a little. I’m a money guy, you know. I try to embrace the persona.”

With that settled, Logan and S. consummated their new arrangement. Twice. In between tumbles, they took a break and S. put on an impromptu belly dancing display, wearing a belly dance belt and nothing else. She began to move, slowly, sensually, making hungry eyes at Logan, licking her lips. Logan didn’t know how to react.

“I’m like a very awkward, neurotic Jew, so I’m just sitting there smiling and clapping along. I didn’t know what to do,” he says. When she finished swaying, Logan gave her one last round of applause and said, “That’s so wonderful.”

“I feel like I’ve mastered approaching girls online,” Logan tells me.

Part of it is a numbers game, of course—the more women you engage, the better your chances of scoring—but Logan has also made small tweaks to his game along the way. For instance, he has tried out a variety of introductory messages until settling on his current one—“cute and funny, nice combo :)”—which he says has been the most successful. (“Every girl thinks she’s funny,” he says.) And he will invoke a literal slow play, waiting an hour to respond to a message after they’ve been pinging back and forth.

I ask if this doesn’t play to a woman’s insecurities. “Oh, 100 percent,” he says. “I live off insecurity. If any of these girls were secure at all, they’d never meet me.”

Over the past year and a half, in between Jewish holidays and 80-hour work weeks, Logan says, he has been on nearly 100 dates under false pretenses—and has taken about half of those women to bed. At the start of each outing, he tries to gauge his date’s interest. “Not their interest in me,” he clarifies, “because I don’t care about that, but their interest in having sex in, like, an hour.”

There was the middle-aged mother he slept with under an oil painting of her 18-year-old Hasidic son. There was the woman who looked back at Logan, mid-coitus, and warned him not to mess with her orgasm. Then there was the dreadlocked beauty who turned out to be the full-time baby-sitter for a Jewish couple he happened to know. (That’s one synagogue he can never go back to.)

There have been some close calls, too, like the time he turned a corner at work and saw a nurse who looked disturbingly familiar. Logan frowned, kept walking, but received a text message minutes later, asking if he didn’t work at the hospital. Or the time he was sitting at a computer, iPhone resting on the desk nearby, visible, and a text displaying someone’s vagina flashed on the screen.

For the most part, though, Logan is able to end each relationship without drama or histrionics, thereby alleviating his guilt and lessening the chance, in his opinion, that some boyfriend or pimp will come calling. “I don’t just drop them,” he says. “I try to present a façade that this could continue. Maybe talk on the phone a couple times. Text back and forth, and then let things fizzle away slowly. I don’t want a girl to feel like I just used her to bang her, even though that’s true.”

Thoughtful, I say.

Logan shrugs. “I think I’m a mensch at heart.”

But of course there’s zero chance for any of these relationships to continue—even with those women who don’t think he’s some tech magnate, who just think he’s an ER doctor or a plastic surgeon or an anesthesiologist, if not a medical student—because Logan says he will only marry a Jewish girl, and he believes dating to be a slippery slope. “Once you give them your real name and your real story, then I think you open yourself to the possibility that you might actually connect with that person, you know?” Logan says. “As long as I’m wearing this mask and have this façade on, it’s always going to be only half-serious.”

He laughs. It’s all a joke. A joke he brings back to his Orthodox buddies, most of whom are married with kids, just drooling for details. And in talking with Logan, it’s easy to see why he frames his exploits as sport. Of late, Logan has gotten a taste of being on the other side of the power equation as well, having recently taken up with a sugar momma. She is 41, Jewish and knows his real name. The morning after they first slept together, the sugar momma offered Logan some money, which he didn’t take.

I wondered why. Did he feel objectified? “I guess so,” he says. “I guess ‘objectified’ would be the right word.”

Logan says he has not accepted cash from his sugar momma. Instead, she simply pays for everything—and he tries not to feel emasculated. She is also considering offering Logan an unofficial consulting job, since her law firm deals with a lot of medical malpractice cases, for which he would receive a sort of salary. Logan jokes that if this were to come to pass, he could become “kind of a sexual Robin Hood.”

“Taking from the rich, giving to the poor,” he says. But the more likely scenario, he says, is that he will eventually be given a key to her luxe downtown apartment, which he could then use to host other girls—like the supposed Playboy model from Miami whom he met through his time on SeekingArrangement but flaked at the last minute, two weekends back. “That would be so wrong in so many ways,” he says, before adding, “but it’d be really helpful.”

Not that Logan is opposed to dating toward marriage, if the right woman were to come along. In the insular world of Orthodox Judaism, Logan is already playing catch-up with his married friends. But finding his bashert (the one he is meant to be with) is proving increasingly difficult as his conquest tally rises. As his buddies’ wives balk at setting him up with their friends, his matchmaking prospects falter.

“Don’t tell your wives that I’m doing this!” he says he tells his friends.

But even if he can keep his sordid social life out of the Orthodox rumor mill, one wonders: what of his eternal God-fearing soul? How can Logan possibly square his actions with his religion?

“The lies?” he says. “I don’t feel like there’s someone keeping track.”

Then why go to synagogue on Shabbos? Why keep kosher? Why do any of it?

“We come from a 3,000-year-old narrative of people doing things the same way,” he says. “It’s not because I fear there’s an old man with a beard up there that’s going to smite me that I do the rituals ... Everything I’m doing is totally immoral. It’s unethical.” But then, just as he seems to be staring the wickedness of his ways square in the face, he begins to backtrack: “With respect to the SeekingArrangement girls, they’re all gold diggers, transparently. They’re not good people. If you can assign a judgment to a person based on their affiliation with a website, I think this is the place you can do it. So I don’t feel that bad.”

As for the PlentyofFish women: “We’re having a nice time,” he says. “They don’t know that they’re being misled. Aside from my name, the fact that I’m an Orthodox Jew, that I’m only going to marry a Jewish girl, that I’m not going to date you or take this seriously—aside from that, I’m totally honest.”

And then he changes the subject, having resolved to suffer no crises of conscience, returning our collective attention to a series of photos on his iPhone, flipping through until we land on an image of a very young woman in a full Batman costume. She is, Logan informs me, 17 years old.

Huh. But wouldn’t she have to be 18 to sign up for a dating site, I wonder?

“It’s not hard to lie,” Logan assures me. “Especially on the Internet.”

Michael Hainey

When Graydon Carter pulled an intern named Michael Hainey aside at the Spy magazine Christmas party in 1989, the legendary editor had probably had a few. “I think you’re going to be a star,” Mr. Carter said. And then the advice he’d repeat over the years: “Don’t fuck it up.”

Twenty-five at the time, Mr. Hainey knew he’d have to move quickly if he was going to make good on his boss’s intuition, since he also believed—beyond reason or doubt—that he would be dead in a decade.

Such was his inheritance.

“For many years, I just thought, ‘I’m never going to outlive my father,’” Mr. Hainey said last Wednesday, in his low monotone. We were sitting in a diner just east of the Avenue of the Americas, kitty-corner from the GQ offices, where Mr. Hainey serves as deputy editor, less than a week before the publication of his new memoir, After Visiting Friends. The book, out this week, details a 10-year search for the truth surrounding the night his father died at age 35, when Mr. Hainey was 6. “That was the thing that defines me,” he said. “I don’t think I’ll ever be free of that day.”

This book represents Mr. Hainey’s latest creative endeavor; he has previously had poems published in Tin House and exhibited paintings at Thom Browne’s Tribeca store. It also may be his most personal. From the time he was 9 or 10, Mr. Hainey remembers a specter of death hanging over him. He had questions about his father, questions about how he’d died, that had gone not only unanswered but, for years, unasked.

“I had tried to imagine his last night,” Mr. Hainey said. “Did he die alone? It frightened me as a boy that no one was with him.”

A Chicago newspaperman, Bob Hainey was found dead in the street on the city’s Northside on April 24, 1970, struck down by an apparent heart attack or cerebral hemorrhage, depending on which paper’s obituary you read. The author’s uncle, also a journalist, broke the news to the family. But there were other inconsistencies. According to one of the obits, he had passed away “while visiting friends.”

“We all long to go in search of our family secrets,” said Mr. Hainey, whose journey into his family’s past didn’t begin until sometime after he had celebrated his 38th birthday, having avoided the Grim Reaper’s scythe. His thoughts kept returning to those obituaries, which he had read at the library as a high schooler when curiosity finally boiled over. Who were these “friends,” he wondered? Why had they never come forward?

Having followed in his father’s footsteps, Mr. Hainey was a newsman now, and his reporter’s instinct told him something didn’t add up.

After graduating from Northwestern University’s Medill School of Journalism, Mr. Hainey worked for a time at The Chicago Tribune, one of the papers that had employed his father. But he credits his first experiences in New York, and his time at Spy in particular, with teaching him the real ins and outs of reportage. He counts Graydon Carter and Kurt Andersen, Spy’s founding editors, as his earliest mentors, as well as Susan Morrison.

“They really taught me what it meant to be a writer in New York, and at that level of ambition,” Mr. Hainey said.

Ms. Morrison, now at The New Yorker, remembers Mr. Hainey, just off the boat from Chicago, as a kind of Jimmy Stewart character. “Before he had the new-wave hair and important eyeglasses and Thom Browne suits, he was this kid with hay in his hair,” she said. “That made him the perfect candidate to do certain kinds of interactive Spy stories. Stories that in another context would probably be called hazing.”

On one such assignment, Mr. Hainey was tasked with chasing after girls on Amsterdam Avenue to test-drive a variety of actual celebrity pickup lines. “He was terrified,” Ms. Morrison remembered. “I think he actually did pretty well with [Warren] Beatty’s line, which was ‘Make a pass at me.’”

Mr. Hainey's new memoir

Anthony Haden-Guest’s pickup line, on the other hand—“God meant for us to be naked together”—did not go over so well.

“He had, from the beginning, in his understated Midwestern way, a combination of confidence and gameness,” said Kurt Andersen, the Spy co-founder-turned-novelist, “just a kind of willingness to do whatever we asked.”

As deputy editor of GQ, Mr. Hainey has interviewed some of the most iconic cultural figures of our time, from Keith Richards to Clint Eastwood to Bruce Willis, the cover boy of the magazine’s current issue. In his book, though, Mr. Hainey talks about how he still needs to get into character before doing reporting. “By nature I’m a shy person. I get rattled easily,” he said.

Perhaps, but there is something of a rascal under his soft-spoken Midwestern exterior as well. When The Observer first met Mr. Hainey, for example, we had been instructed by the writer Donald Antrim to give him the middle finger, because that was how Mr. Hainey caught Mr. Antrim’s eye at a party two decades back.

During those early days in the city, Mr. Hainey lived in a Quaker-run boarding house on 15th Street, where, in exchange for a bed, a desk, two meals a day and a communal bathroom, he paid a token rent and did chores, like washing dishes and shoveling the sidewalks. “It always seemed to be snowing,” he recalled.

Now Mr. Hainey is a perennial front-rower at fashion weeks the world over, and along with his wife, Brooke Cundiff, an executive at Gilt Groupe, he represents one-half of a New York fashion power couple. Mr. Carter describes him as a loyal regular of his exclusive West Village watering holes, the inns Waverly and Beatrice, so “I see a lot of him through the bottom of a highball glass.” But none of that mattered when Mr. Hainey found himself trolling through Chicago hospitals and morgues, chasing after the ghost of his father. Or when he found himself face-to-face with the men who had worked alongside his dad back in the day, grizzled newspapermen who still played by an old-school code of silence, admitting nothing but betraying everything.

“Guys stick together,” they said.

“I don’t think you have the right to know the truth,” they said.

The stonewalling did not discourage Mr. Hainey, and clues began to materialize. (“I’m not a talker. I’m an observer,” he told us.) The author questioned family members, sought out his father’s high school classmates and even forged signatures in order to get hospital records released. Precious, long-forgotten hospital records. He did not begrudge those who got in his way. He just had to get past them.

“I had to know,” Mr. Hainey said. “What was that story?”

In a sea of self-discovery memoirs, After Visiting Friends stands out for its level of journalistic inquiry. “Too many memoirs are ‘me me me,’” Mr. Hainey lamented.

And while the book may have paternal-thematic ties to Zachary Lazar’s Evening’s Empire and either of David Itzkoff’s efforts, it shares most of its DNA with David Carr’s The Night of the Gun, in which Mr. Carr goes back in time to report on his own life. “The art of reporting” is as important to Mr. Hainey as it was for his father. And in the end, this doggedness is what brings Mr. Hainey to the truth about his dad—and to the fear that this truth may destroy what is left of his family.

Bob Hainey with his two boys.

“It’s one thing to be the truth-seeker,” he writes. “It’s quite another to be the truth-bearer. The delusion destroyer. There’s a reason people don’t like revisionist historians.”

So he sat on his newfound knowledge for well over a year. Guilt crept in, as it had throughout his search, when Mr. Hainey wrestled with his own responsibility to his father’s secrets. “Who do you think you are? I made you,” his father would say in their imaginary conversations.

On one hand, the elder Mr. Hainey ought to be proud of his boy. As the author says in the book, “Everything my father and uncle valued in newspapering—good reporting and editing—in the end, it’s what undid them.”

And yet Mr. Hainey admitted that he had “great feelings of disloyalty” about revealing his father’s secrets. “Even though I was a man in my 40s, I still saw him through the eyes of a 6-year-old,” he said. But he knew what he had to do. “There was a lot of doubt, but I had to tell my mother what I’d found out.”

Just as he had to get into character so as not to “let the barking dogs” of journalism scare him, Mr. Hainey felt these were similar fears that had to be overcome. In fact, when asked what advice he might give to some theoretical future son, or what advice he wished he could have received from his father, he said, “It’s about living your life without fear, going toward what you want.”

And 40-plus years later, he is doing just that. Mr. Hainey is already plotting two follow-up works, including a novel, and is in the process of moving into a new painting studio in the West Village.

With all that, surely Mr. Hainey has lived up to that old Christmas-party prophecy.

Then again, Mr. Carter sounded less than unequivocal in his assessment of Mr. Hainey: “I think Michael has proved himself in a number of fields,” the Vanity Fair boss said. “If I could just get him into a suit that fitted him, he’d really go places.”

Amy Schumer.

Outside of Joe’s Pub last Wednesday night, a line stood dozens deep as savvy comedy fans and plaid-shirted beardos waited to see if they’d make the cut. Inside, black-clad waitresses tended to the booths and tables. Stagehands hustled to prepare the room. And somewhere in the wings, Amy Schumer waited to take the stage, possibly sweating.

The Transom found a vacant stool by the bar, alongside indie filmmaker and Brooklyn resident Jim Strouse, huddled around a pint of Smuttynose and trying his best to avoid confrontation with the theater techs and Comedy Central cretins that barked orders and directed traffic every which way. Why was everyone so angry, we wondered. Mr. Strouse had no answers.

“I don’t know anything about this,” he said.

What we did know: Ms. Schumer, a 31-year-old actress and comedienne, is a rising star in the world of setups and punch lines, having capitalized on her breakout performance at the Comedy Central Roast of Charlie Sheen in late 2011. Last year, she appeared on Louie, a coup for any New York comic, and she will reportedly pop up on the current season of Girls. This spring, she hopes to grow her audience even more when her new show, Inside Amy Schumer, premieres on Comedy Central. Hence the hoopla. Because on this particular night, Ms. Schumer was to film the stand-up segments that will serve as interstitials between the program’s sketch scenes.

And soon enough, the woman of the hour graced the stage, dressed in a black mini-sweater
dress and matching thigh-highs—a look Howard Stern has told the comedienne he finds particularly, if curiously, sexy.

“Am I sweating? Feel like I’m sweating,” Ms. Schumer said, her set underway, complaining about the thickness of her Spanx. “Can you call them Spanx if they’re made of metal?”

As a performer, Ms. Schumer radiates a sort of wide-eyed joy. She doesn’t shy away from sexual or scatological topics, or from the occasional self-effacing barb. Her laugh lines are all the more biting for the package from whence they come: a bubbly blonde with an effervescent smile. She’s like a joke-telling Tracy Flick, without the crazy.

If Wednesday night’s set was any indication, fans will be pleased to learn that Inside Amy Schumer will deliver the same mix of sexual vulgarities, comic rope-a-dopes and off-balance irreverence that Ms. Schumer has always provided, from 2007’s Last Comic Standing to last year’s standup special, Mostly Sex Stuff. Male orgasm faces? Check. The size of her vagina? Double check. How all women have been a little raped? And how.

Fans will also be pleased to learn that she absolutely killed, pumping the brakes only occasionally on her rapid-fire funny, and then only for a bit of crowd work. One young man with a lumberjack beard and a polka-dot hoodie was squarely in her crosshairs, but Ms. Schumer also took the time to ask another front-rower whether she thought the Holocaust happened.

“Me too,” Ms. Schumer nodded. “I’m a believer.”

By the end of the set, Ms. Schumer was fielding some questions herself. One audience member wondered if she is related to Senator Chuck Schumer. Her answer: “Only when I’m arrested for shoplifting.” (Her father and the senator are indeed cousins.)

Another wondered, how big is too big? To which she replied, “We covered that.”

And finally, a fan wanted to know if she could have a picture with the star of the show? “I’ll get you on the way out,” Ms. Schumer smiled, ever accommodating. “But I hope you like sweat.”