Tara* had struck gold. After spending a lazy Saturday afternoon browsing through the dating app she was currently experimenting with, she hit it off with a nice-sounding guy, and the two exchanged real names and numbers. She found herself Googling Stuart*, a Brit living in Amsterdam. He worked at a startup; he was visiting New York on business. “I was like, oh, he’s kind of cute…”

Eat Pay Love Lede

Eat, Pay, Love

A new app lets women charge for a night out. Will dating join the on-demand economy?

Eat Pay Love Divider

By Emily Yoshida | Illustrations by Beady Eyes

Tara* had struck gold. After spending a lazy Saturday afternoon browsing through the dating app she was currently experimenting with, she hit it off with a nice-sounding guy, and the two exchanged real names and numbers. She found herself Googling Stuart*, a Brit living in Amsterdam. He worked at a startup; he was visiting New York on business. "I was like, oh, he’s kind of cute…"

Neither had plans that night, so they started figuring out where they could meet up for a drink. When Tara suggested a restaurant in midtown Manhattan, Stuart was into it: "Okay cool, my hotel is super close to there," he messaged back. The mention of the hotel gave Tara pause, and she asked him what exactly he had in mind. "We can go back after and have some fun," he said.

Tara hesitated. This guy seemed nice and normal and safe and she was down for a fun night out with a visiting stranger, but she drew a hard line when it came to sex on the first date. "I was like, ‘Listen, I don’t know who you’ve met [on this app], but I’m not going to fuck you, I’m sorry,’" she says. Her match was taken aback. "Oh," he responded. "I thought that was the expectation."

These kinds of conflicting agendas will be familiar to anyone who’s done much Tindering or Bumbling or OkCupiding, where one person’s one-night stand is another person’s chance at finding The One. But Tara wasn’t using any of these apps. This was Ohlala, and Stuart had already agreed to pay Tara $600 for their date.

Heart Section Breaker 2

The Ohlala headquarters are located on a sleepy block in the Prenzlauer Berg neighborhood of Berlin, in an old prewar building one block from where the Wall once stood. Though you wouldn’t know it from walking down the pin-drop-quiet residential street, the neighborhood has become home to several startups including SoundCloud, which has an office a couple floors down from Ohlala.

When I arrive, there’s a mood of weary intensity among the eight or so team members present. Pia Poppenreiter, the company’s CEO, stands and greets me with a rushed hug. "You picked a great day to visit," she says, in a voice that suggests more cigarettes than hours of sleep. "Search ‘hashtag escortgate’ on Twitter." I do so as we step out to the balcony and she lights up a Marlboro Red. A pink Ohlala banner tied to the railing billows silently behind her.

Launched in August 2015, Ohlala is a web-based app that facilitates what it calls "instant paid dating." Male users post offers for dates, consisting of a time, a duration, and how much money they’re willing to pay — a typical offer is from 1–4 hours at an average price of $300. While the request is up, women can decide whether or not they’d like that person to be able to contact them. Crucially, women are not visible to men before they initiate conversation — it’s the inverse of the backpage listings to which it’s often compared. Here, the buyers must come forward first. From there, the couple can chat and discuss the whens and wheres of their impending dates, as well as a payment method and their boundaries, if they so please. (In-app payment is currently in the works, the team tells me.) When the terms are agreed upon, the chat is logged, and presumably both parties are incentivized to show up. Though its on-demand model has earned Ohlala the label "Uber for escorts," the company insists it isn’t an escort agency, or even operating in the adult entertainment space.

As I scrolled through the largely German #escortgate hashtag, one Bing translation at a time, I started to piece together an unraveling scandal. That week Berlin had been host to the NOAH Conference, an invite-only event comparable to Code Conference or Disrupt back in the States. According to multiple reports, the gala party two nights earlier had been characterized by a high number of "attractive, glamorously dressed women" who flirted aggressively with the male attendees and handed out business cards. It was concluded that these women were escorts, and that they had come to the party at the behest of Ohlala. Several women were rumored to be carrying credit card readers.

Glued to her Twitter feed as we sit on the deck, Poppenreiter dismisses the credit card part, at least, as "ridiculous." But, she says, "It’s true, to some extent. We did invite people [to the NOAH party], but it was more my friends." Her all-female guerrilla marketing team were dressed up, sure; it was a party, after all. Several in the group were Ohlala users, but Poppenreiter puts those numbers in the low single digits. Poppenreiter herself did not join them. "I was exhausted, I was at the conference the whole day."

There’s no question the group was pulling off a stunt. A leaked Facebook invitation for the party-within-a-party encouraged invitees to "grab a drink and mingle with men who crave the finer things in life." A publicity stunt involving a controversial app doesn’t sound like the stuff of trending topics, until you consider NOAH’s abysmal female attendance rate — at this year’s event, only 11 out of its 108 speakers were women. The presence of escorts at the evening events have long been a wink-wink assumption. By symbolically associating themselves with these women, Ohlala’s party crashers made the company a scapegoat for these rumors. But they also got people’s attention.

Poppenreiter had already released a statement earlier in the day in response to the outcry, apologizing for letting things "get out of hand." But part of me can’t help but wonder if this was exactly what she had planned.

Heart Section Breaker 2

According to Poppenreiter, Ohlala seeks to improve upon two perceived flaws that Tinder and other dating apps often fall into. First, the in-app chats that go nowhere — or worse, promising matches who ghost on you. As more results-oriented users of Tinder or OkCupid can attest, if you’ve logged on with the objective to meet up with someone that night, you can often be left frustrated. With Ohlala, everyone wants something, and everyone’s on a tight schedule.

And then there’s expectation management. People use Tinder or OkCupid for everything from NSA hookups to long-term relationship hunting, but there’s a high likelihood that you and the person you’re courting electronically might not be on the same page, even if both of you put "casual dating" in your "looking for" field. The chat stage of Ohlala prompts you to be up front and clear about what you want. If you are definitely not open to having sex on your date, you can establish that there. If you want to bring a third, you can propose that as well. Either way, the goal is to get exactly what you want that night.

Getting exactly what you want as quickly as possible is the general goal of countless other startups. But because the "what" in this situation isn’t cars or bánh mì but human companions, Ohlala, and other apps that facilitate paid dating, are most easily understood in terms of sex work. This isn’t a huge roadblock in Germany, where the app first launched, and where sex work is legal. But in February of this year, Ohlala crossed the Atlantic and launched in New York City, where not only are the laws different, but social interface is as well. Sure, sex workers and escorts can find plenty of work here, but it remains to be seen if we’re comfortable calling that "dating."

In Poppenreiter’s vision, Ohlala is an app for any woman who thinks she ought to be compensated for her time and efforts when she goes out with someone. It seeks to turn leisure time — a precious, dwindling commodity — into billable hours. In that sense, Poppenreiter’s right: her app isn’t really an "Uber for escorts." It’s a TaskRabbit for emotional labor. Perhaps that makes it more radical than anything else — with its tasteful design and young, hip founder, Ohlala suggests a world in which there’s no "kind of woman" who sells her time and affection, because every woman could be that kind of woman.

Eat Pay Love Section 1

Pia Poppenreiter is hardly a stranger to provocation. The first time I met her was at an Ohlala party at SXSW, where she held court while inviting guests to draw interpretive vaginas on sketch pads distributed around the bar. ("You are going to come. Let us tell you when," the pastel-pink party invitation read.) But the second time we meet, I barely recognize her. In her casually conservative street clothes — chambray button-down, messy updo — she looks more like a J.Crew model or Lauren Conrad acolyte than the bawdy Berlin cybermadam whose name elicits you-can’t-be-serious emoji eyebrow raises on German Twitter (in German "Poppenreiter" can roughly translate to "fuck rider").

Poppenreiter was born in Schauersberg, Austria, a town of about 5,000 people, and the kind of village where everyone knows your name and your business. She originally came to Berlin for grad school to study business ethics after a year of working in finance in Frankfurt. She was in between jobs, and out at night with some friends, when she noticed sex workers looking for customers on the icy-cold streets. It was 2013, apps like Seamless and Handy were starting to introduce an on-demand lifestyle to the modern city-dweller and the whole process of waiting around on street corners struck her as rather impractical. She struck up a conversation with the women and got the idea for her first startup.

Peppr is a service that functions like a smart backpage, allowing escorts and prostitutes to list their services, prices, and photos in a searchable, location-specific interface. Payment is processed through the app, and clients and "Pepprs" can negotiate the specifics in the in-app chat. Poppenreiter researched her user base relentlessly, spending months in Berlin’s streets and brothels talking to sex workers and figuring out what her potential customers needed.

When it launched in Germany in April 2014, Peppr was met with scandalized headlines from around the world, and a huge amount of buzz. But only months later, Poppenreiter was backing out of the company. "I was overwhelmed being the CEO," she says. "I had no experience as such." The viral storm and influx of users to the tiny startup proved to be a mixed blessing. "We weren’t ready, as a team, as a product, nothing."

Shortly after stepping down she was back out there, mixing it up at an Axel Springer networking event. It was there that she met Torsten Stüber, a computer science researcher turned startup founder who would become the CTO of Ohlala. His artificial intelligence company was floundering, and he was looking for his next move.

When Pia showed up at the party, whispers spread — Oh, that’s the Peppr woman. That’s the founder of the prostitution app. Stüber himself had never heard of her or Peppr before. "I said, ‘What? Someone’s doing this?’" He was a little wary of her at first, but they got to talking, and something clicked. "I said from the very first day we met that we would be great co-founders," Poppenreiter says, in a "told you so" kind of voice. This was late 2014. By March 2015, less than a year after Peppr’s launch, the two had started work on Ohlala.

At first glance, Ohlala could just be seen as Peppr with a different color scheme. But the ways in which it differs are telling. For one, there is no way for women to pay for dates with men, or for same-sex dates to occur. (I ask several times about when that upgrade can be expected; each time the response is "eventually.") There’s the aforementioned female-initiated communication process. But what Pia would probably consider its biggest innovation is its time limit. Each open date request only lasts 21 minutes; once a couple starts chatting they have one hour to decide whether or not to go on a date. Using it was a panic-inducing experience, even when I was only looking for male users to interview for this piece. (Which was largely unsuccessful: "Lol! Seriously! This is just like any other dating app. Nothing special," said one user to my journalistic inquiry.)

The time limit doesn’t help Ohlala’s "totally not a sex app" claims. We are humans; our most urgent, time-sensitive needs are usually driven by either hunger or horniness. It’s hard to imagine a situation in which I’d only give someone 21 minutes to decide whether or not to have a stimulating conversation with me over a nice Chianti. But other people are perhaps more likely to be drawn in by the promise of such instantaneous interaction, with or without sex — people who are (or consider themselves to be) very busy, very important, and very impatient.

Poppenreiter isn’t a terribly patient person, which can be a helpful trait in the startup world. She literally cut her losses when she sensed Peppr wouldn’t pan out. When Ohlala expanded to New York City, it was a similarly impulsive development. "We were a very small team at that time, I think just six or seven people," Stüber says. "And we said that we wanted to be done within two months — going to a new continent, filing a new corporation, checking the legal situation."

The legal situation, of course, is less permissive in New York than in Berlin. But the cultural situation is really what Poppenreiter is trying to disrupt, despite the fact that the team did no substantial market research before coming to the States. During our conversation she’s careful not to use words like "escort" or "sex worker" when describing the women who might use Ohlala (the app’s website states in no uncertain terms that escorts are "not welcome" to use the service). Everything about the site’s tasteful pastels screams "This is normal! This is for you, normal girl! We’re all normal! We all charge money for dates!" But no matter how much Poppenreiter may be trying to redefine our attitudes around paid dating, in the United States, what she’s selling exists in the same legal loophole as escort agencies. Charging money for a date is still charging money for a date, whether it’s your sole source of income or not, and it’s hard to unseat centuries of religious and moral baggage that come with the American Dream. You can tell yourself you’re just a resourceful girl looking to offset the cost of cab fare and a personal trainer, but in the eyes of the law, you may as well be a hooker.

Eat Pay Love Section 2

Tara is not a hooker. Nor is she an escort. She’s a matchmaker, as it so happens, specializing in the "sugar dating" niche. She found out about Ohlala in the course professional research, and signed up hoping to use it to find eligible women for her wealthy male clients to meet. "When I realized I couldn’t," — Ohlala’s structure means that there’s no way for women to contact other women — "I [thought], well, maybe I’ll just meet cool guys."

When I talk to her, on a balmy afternoon in Manhattan's Bryant Park, she just finished lunch at Koi. She sports oversized Prada sunglasses and a patent leather Chanel bag. She’s an animated, mile-a-minute talker — it’s easy to imagine her being great on first dates. She’s just been using Ohlala for a couple months, but so far, she says, "It’s more rubbing me the wrong way than the right way." Many of the male users assume from the jump that she’s an escort, and kick off the chat by asking for nude photos and specific sex acts. There’s also a transparency imbalance: Ohlala boasts about its verification process, but far more women than men bother to add photos (something I can corroborate, having spent time on both sides of the app’s gender line). "I hate that guys who have unverified profiles will say ‘I need you to send more pictures. I need to see what you look like,’" Tara says.

Which leads to another issue. Tara’s black, and she’s experienced a fair amount of prejudice on the site — and in a more blatant way than she’s experienced on Tinder. "I don’t think it’s racism," she says of most guys’ behavior. "The racism comes when they’re hateful. They’re not hateful, they just don’t know, and they don’t say it right." One potential suitor, after ending their chat abruptly, came back to apologize — he didn’t mean to be rude, it’s just that he didn’t like "African-American girls."

Tara appreciates Ohlala’s underlying philosophy, but in practice she’s found it to be much more dicey. "They say to you, as a woman you have all the power, you can either accept or deny something. You lead the conversation, you only agree to what you accept." But it’s hard to feel like you have all that power and agency Ohlala promotes when a gray silhouette is hounding you for nudes.

"Guys will go, ‘Well look at the site you’re on. Obviously I expect this.’ I’m like, ‘You know what? You’re right!’ I just leave the chat. Because what can I say?"

Heart Section Breaker 2

Poppenreiter prefers the term "paid date" to describe what Ohlala provides its users. She claims the reason for this is as philosophical as it is legal: "You can’t use an old word for a new idea," she’s said to me, and at least a dozen other publications she talked to during the app’s US launch.

But the idea of paid dating is hardly new. And if it is, it’s just as new as the idea of dating itself. In her book Labor of Love: The Invention of Dating, Moira Weigel explains how dating as we know it today rose up around the turn of the century as a working class practicality — a way for urban singles living in cramped family apartments and boarding houses to get out and spend their wages while enjoying a little romance. (Middle and upper class singles were relegated to the practice of "calling" — a formalized form of courtship largely conducted under the watchful eye of a parent.) But the market was far from equal: "Despite the record numbers of women entering the workforce, the belief remained widespread that they were working not to support themselves but only to supplement the earnings of fathers or husbands," Weigel writes. "Employers used this misconception as an excuse to pay women far less than they paid men." Less than half as much, on average — which meant when it came to spending money on leisure, women did not have nearly as much financial freedom as men did. Accepting dates with men primarily as a way to get out of the boarding house for the evening was very common among the textile workers and seamstresses of New York City.

Wage equality in the United States has slowly crept toward parity over the course of the last century, but when it comes to the big bucks, men still vastly outpace women. According to a report this year, only one out of five CEOs in the US is female, and only 12 percent of the world’s board seats are occupied by women. The numbers for women of color drop even more precipitously. At the same time, female-targeted consumer culture has only intensified since the turn of the millennium, along with our growing access to the lives of the rich and / or famous via tabloid journalism and social media. We always were aware that there were people who had better, more expensive things than we did, but now images of them stream past our eyes every day. Maybe this serves as inspiration for some to work harder for that next raise, but the fast track to the high life as portrayed by the Kardashians (or whatever affluent lifestyle porn floats your boat) is to "date up." Having a relationship with someone you might not otherwise pursue, the thinking goes, is a small price to pay for your material self-realization.

Sites like SeekingArrangement have profited off these appetites, and helped perpetuate the notion that rich men want to date gorgeous young women, and gorgeous young women want to stay in five-star hotels and wear Celine. Brandon Wade, founder of SeekingArrangement, has become somewhat of a mogul in the field of transactional dating, having launched a network of compensated dating sites. In many ways, he’s the anti-Pia — his sites are unapologetically marketed toward male users ("The odds are in your favor," the landing page proclaims while boasting its 4–1 baby-to-daddy ratio), and his business model is built on a prescriptive life philosophy in which women only need to be plied with gifts and money in order to "expand their horizons" when it comes to which men they’re willing to date.

In 2007, he launched WhatsYourPrice, a more cut-and-dry version of SeekingArrangement, predicated on the idea that everyone has a dollar amount at which they’d be willing to give someone a chance on a "first date." It’s the most clear existing competitor to Ohlala, in that its daters deal in cash, not the ambiguous promise of "gifts." A first date is the beginning and end of its immediate goals. But nearly a decade later, its membership remains about one-fifth the size of SeekingArrangement’s, Wade says. "Primarily because it can be argued that a sugar daddy is just a wealthy and successful boyfriend who’s willing to be generous towards you." An ongoing "arrangement" provides enough ambiguity that both parties can choose to unsee the monetary exchange at the center of it. The clearly labeled price tags on the users of WhatsYourPrice, and now Ohlala, are harder to ignore. "As you trend toward the more transactional approach to dating, it does become less acceptable," says Wade.

In a way, this means that its users really have to want to do what they’re there to do. One of Ohlala’s selling points is its strict policy regarding no-shows — that’s one way it preserves its "instant" and "on-demand" selling points. But if a female user suddenly gets a bad vibe from her date, must she still show up at the risk of getting kicked off the service? And if she does show up, how does she guarantee payment if her date deems the evening unsatisfactory? In the end, what’s on demand, and who’s demanding? Ohlala may put more power in the hands of women when it comes to vetting dates, but the only people who are finding dates on demand are the men. Women are first and foremost finding work.

Eat Pay Love Section 3

It’s tough to be a female entrepreneur. Perhaps that’s why the people who are most upset by Pia’s escortgate stunt were those who felt their work was most invalidated by it — her female peers. "Being a founder myself it was obvious to me that [they] were not founders, nor investors but girls that were invited for entertainment purposes," read one woman’s account of the NOAH party.

Back at Ohlala HQ, this is what Poppenreiter still can’t get over — what she calls a "double-moral" within the tech industry, especially in Berlin. "People say, ‘Oh my god, those girls, they wore skirts and high heels; they’re hookers.’" She says, "Okay, so, if you’re wearing a skirt, and if you’re wearing makeup, then you’re a hooker?" She turns back to her feed, and laughs bitterly when she reads a quote from a female entrepreneur who attended the party. "Crazy — women saying ‘I’m glad I wore a business outfit so no one would mistake me for an escort.’" (As it happens, many female entrepreneurs were mistaken for escorts by their male peers, when Poppenreiter reads this she laughs again, this time with a little more schadenfreude — "Oh man, now I wish I would have been there," she says.)

Suffice to say, Poppenreiter comes from a different school of thought than many of her fellow female founders. "I always say, I’m a woman, and I’m a woman in tech. And I don’t want to dress like —" she stops short. "I was wearing a black dress on the first day I attended NOAH, because I want to be a woman in a male-dominated environment. I don’t want to dress like a guy." And yet, she rejects much of the female tech community — their meetups and initiatives and representation quotas, which she considers reverse discrimination. "I think women in the startup community are so aggressive about their points, and I don’t think that’s the way to create the greatest amount of change in the shortest period of time," she says. "What I want to do is be an excellent CEO, and accomplish that myself, and then be a role model because I accomplished that myself."

That Ohlala’s founder is a woman — and that she’s hired a staff that’s over 50 percent female (an anomaly in tech) certainly helps with public perception. But it’s also a double-edged sword, and Poppenreiter is continually fighting to be taken seriously as both a CEO and a disruptor of the still largely feminine-encoded dating industry, especially at events like NOAH. Not that she’d ever let on as much. "Pia experiences this every day; I don’t, because I sit here when Pia goes to events," Stüber says. "And she does not talk about this, because Pia is [busy] proving that she’s really good at what she’s doing. So it doesn’t come up."

A few days later, Poppenreiter posts a follow-up statement, this time on her Facebook page. "We could spend time discussing how unfair the world is and how we disagree with the tendencies of a [formerly] heavily male influenced industry," she writes with barely concealed disdain. "You choose. And I will roll up my sleeves and go back to work now."

The work pays off; just a few days after #escortgate, marketing director Lindsay Buescher says she estimates signups have increased by 700 percent.

Heart Section Breaker 2

During my conversation with Tara, a homeless man approaches, looking distraught enough that neither of us can ignore him. He’s lost his wallet and his ID, he says, and he’s just looking for money for food and to travel back home. We each hand him a dollar; he thanks us and moves on.

As soon as the man’s out of earshot, Tara tells me about a video she watched that weekend, about a homeless man who seduced women for shelter. "He’d go to Walgreens and Duane Reade, and just freshen up using [hair gel.] He would go bar hopping, and he would sleep with girls, and he was like, ‘Depending on how good I fucked them, I could stay a three-day weekend.’"

The hustle is real, and Tara has few illusions about it, which is why she had few qualms about signing up for Ohlala. "People will let you exploit them to a certain extent, and they’re okay with it," she says. "I thought, if I can get paid to just go on a date and just be my loud, crazy, fun self, why not?"

And yet, almost despite herself, she thinks she may have found someone she really likes. Stuart? From Amsterdam? After getting over the initial miscommunication hump, they ended up going out anyway, with the understanding that sex was not on the table. She still got her $600, too — he PayPal’d her, and, like a true gentleman, waited to make sure she received the transaction before saying goodnight. "He was like, ‘Just know this is for your time.’

"He’s actually really cool," she says. "He’s someone that I’d right swipe on Tinder anyway, so it was totally okay." Their date turned into a few hours of bar hopping, and ended with a little bit of making out.

"Sometimes it’s nice," Tara says. "I’m single now. It’s nice sometimes, to be in the company of a guy that I’m attracted to and see where it goes."

"I’m 100 percent certain I’ll fuck him," she says, with an ear-to-ear grin. "I like him."

But throughout our conversation, she vacillates wildly on whether or not the feeling is mutual. They still text, but Stuart has a wife and kids — even on their first (relatively) chaste date, he expressed doubts about straying from his marriage. The money only clouds the issue further. Perhaps, she says, she would have been open to sleeping with him after the night went so well if they had met any other way. But she couldn’t trust herself in that transactional space. "I’d feel like… well, did I only do it because you gave me money? I don’t know."

For this, and the reasons she’s already expressed, she’s probably deleting her Ohlala account. In the meantime, if she wants to set up another date with Stuart, she has his number. He’s supposed to be in town later that month, and they’ve even discussed plans for a second date (Smorgasburg!). And because she likes him so much, she’s lowered her fee — just $300 this time.

*Names have been changed to protect identities.

Eat Pay Love Divider 2

Design by James Bareham

Edited by Michael Zelenko