Washington - His first message arrived in November. I was surprised to see his face pop up on Facebook messenger.
Alex was newly married, with a baby on the way. The last time we'd talked had been five years earlier, when he asked me to come over and have sex, and I'd countered by asking him to take me on a date.
The flirtation had started on the mats at our upscale gym in Santa Monica, California, lasted through months of my staring at the star tattoos on his oversize calves, through heart-racing banter by the weight machines, on to Facebook messages, which never went the way I wanted. It ended, finally, at our stalemate.
I had since forgotten all about him.
So when he messaged to ask if I could help him market his yerba mate beverage to my company, which runs surf contests around the world, I ignored him.
In March, he messaged again.
"Hey Anna, how are you?" he asked. "I know you're not ignoring me."
In the four years since I'd started my job as a senior editor for a surf website, I'd faced a light mist, then a gentle rain and, finally, a deluge of queries from men I'd met through romantic avenues - from dating apps to past dates to, in this case, a passing flirtation - who arrived through all means of digital avenues to ask for professional connections.
Alex's ask was among the most oblique, but others were more direct. Beneath my casual swipes on apps, as I tried to date between long work trips and sometimes on the road, was a fear that I was only worth as much as my work.
The messages I was getting from would-be flings and digital suitors who were more interested in job openings than dinner dates ("r u hiring?") recast those lofty and formative years. Finding a meaningful career and cultivating success had been everything. But could the very thing that I felt made me me, in large part, have become the barrier to a future family? The promise of my generation suddenly felt like it had been false all along.
I considered my anger. If Alex had messaged me on LinkedIn, a site for professional networking, his note would not have felt as brazen or self-serving. If I - still single, 40, with my eggs on ice and a $12 000 loan to pay off for that biological insurance policy - were settled with a partner, would I feel such an affront? Had I, who dreamed of bylines more than weddings, made a trade that I couldn't take back?
I'm not sure. But according to anecdotal evidence and social scientists, I'm not the only one getting such odd requests, nor am I the only one fearing such Faustian pacts.
While making professional asks on personal platforms aren't necessarily inappropriate, they don't "feel right," either, says Stephanie Tong, an associate professor at Wayne State University in Detroit who runs a lab on digital dating. "Social media brings all of our worlds together - academics call it 'context collapse.' ... Digital media collapses it all in your space online and makes it very confusing."
Some chalk up this type of misaligned purposes to the relatively short time that dating apps and sites have been around.
Alex Williamson, head of brand for Bumble, thinks that because "there have been no rules, and no regulation ... people feel they can treat each other differently than you would in person." One of Bumble's goals, she said is to educate its users on how to behave more civilly in the digital space - an initiative that could easily apply to all corners of the Web.
Along with not having a user manual for dating in the digital age, there's often not a clear separation between someone's personal and professional lives. Someone's profession and place of work are treated as shorthand for their interests, lifestyle and socioeconomic class. "You have to push your identity and distill it down into something that's digestible," Tong says. "Whether that's good or bad, I don't know."
Tong suggests being forthright with your prospective dates if two people seem to have different intentions. "You recognize, 'I have a set of specific expectations when I go into those dating platforms, but not everybody has the same expectations,' " she says.