What’s the Etiquette of Hooking Up With ‘the Help’?

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Photo: Tristar/Columbia Pictures

Alicia* wasn't sure what to do when the TaskRabbit she'd hired finished building her Ikea Billy bookcase, wiped his hands on his jeans, and asked her out. "It's not like he was some old guy with plumber's crack," the 27-year-old Cobble Hill resident said later. "He was a good-looking guy, and I think he had a degree from like, Brown." But she’d just paid him. Technically, he was the Help. And you’re not supposed to date the Help — right?

It’s been two decades since Seinfeld wondered if he was a john after sleeping with his maid, and we’re still not clear on what the rules are when it comes to the upstairs-downstairs romance. Ben Affleck and Jude Law were subjects of scorn after sleeping with their nannies. But time and the sanctity of marriage have indemnified Ethan Hawke, who married his kids' nanny, and Matt Damon, who took home the bartender. Still, even when these relationships have every indication of being “real,” there’s something sort of odd about them. (For instance: How weird was it when, after Heidi Klum broke off her 18-month romantic relationship with her bodyguard, a source told People,“They are no longer working together”?) And the rise of the so-called Gig Economy, with its vast armies of temp, on-demand labor, has created a wealth of new, even grayer opportunities for people to blur the lines between work and play.

Over the summer, a series of posts on Whisper suggested that “fucking Uber and Lyft drivers is apparently a thing,” and travelers utilizing Couchsurfing, a kind of proto-Airbnb in which users pay to sleep on someone’s couch, have so frequently ended up in hosts' beds that the site has a second life as a hookup app. “I've been asked in for a drink,” Jordan, a brawny blond delivery “ninja” for laundry-delivery service Washio, told me in an interview, and while many women raise valid concerns about safety he, like a lot of other guys, seemed to kind of revel in it.This is the next level of playboyhood!” one would-be Airbnb host wrote in a forum. “Getting paid for our services!”

A request posted to TaskRabbit about whether hookups were commonplace elicited several responses — "All the time!" — before quickly being flagged as inappropriate and deleted (soon after, the company changed its requests format, and did not respond to requests for comment on this story). Anecdotal evidence suggests the platform has brokered at least a few off-the-books dates: Kara, 30, had just broken up with her boyfriend when she hired a TaskRabbit to paint her room in Gramercy. "I ended up getting this guy, David,” she told me. “He shows up and he is admittedly wearing cargo shorts and a T-shirt, but he’s really cute and nice. It turns out he's a naval architect and he was just doing this for fun. I was like, hmmm."  

Kara wasn't ready to date yet. But later, after paying Dave his $75 and sending him on his way, she emailed him: Would he mind being set up with her friend, Phoebe? "I was surprised that he was totally into it."

"So Kara texted to ask if I would go out with her random TaskRabbit," says Phoebe, who naturally asked why her friend didn’t want to date him herself. "She was like, 'Too soon. But he’s really nice and normal!’” Kara passed Dave’s number on, and Phoebe confirmed that her friend was right: “He was cute and tall and nice and normal." But although they went out four or five times, ultimately the relationship fizzled. “It wasn’t a bad experience,” she said. But she wasn’t sure if she could see it long-term. “I don’t know if I could like, marry the TaskRabbit,” she said. “But he’s still in my phone. Dave TaskRabbit. I might call him if I need, you know, a room painted.”

Recently, another friend of Kara and Phoebe’s began dating the host of an Airbnb they stayed in on a girls' hiking trip upstate, raising a whole new set of questions. "The first time, she paid,” says Kara. “Since then, she hasn’t had to pay when she went up because she is sharing his room." But if Kara and her new boyfriend go up for a couples' weekend, would they have to pay?

As yet, it’s unclear, but having now experienced more than one of these situations, their group has settled on "a general rule of thumb," when it comes to sex and the sharing economy: "The Airbnb host or the handyman is fine," says Kara. "But you can't go out with the cleaning person. There's just something weird about sleeping with the maid."

*All names have been changed.