“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.”