In April 2019, I had tens of thousands of dollars in student loan debt and was scraping by in New York, working as an editor at a major media outlet making $58,000 per year and living with multiple roommates.

Then I did my 2018 taxes and discovered I owed the U.S. government $2,798 and New York state $345 from the full-time freelance work I'd done the year before.

I made a long-term plan to pay it off but apparently clicked the wrong button and woke up the following day to discover an alarming new bank account balance: negative $1,243. Like most Americans, I did not have $1,243.

I was lucky. A family member was able to lend me $1,243 at no interest, as well as an extra $50 so I wouldn't starve till my next payday. But I did need to pay back the money as soon as I could.

I started looking for work outside of my day job to help cover the bill. Among the various side hustle sites I perused was internet jungle Craigslist. That's when I saw an ad I couldn't really believe.

"Help me find love online," it read.

'You will facilitate some dates with guys who have all their teeth'

"Looking for a funny, smart writer, actor or creative to online date for me," it began.

"I will give you access to my accounts. You will facilitate some dates with guys who have all their teeth, a job and some other criteria I'll tell you about later. You can do it while waiting for the bus, from your couch, from the toilet." She was a local creative, she wrote, and was tired of the online dating grind. She wanted someone to handle the apps so she could just show up on the dates.

Qualifications for the gig included the following:

• "Must writing goodly — seriously, though, I'm trying to match with intelligent, well-educated men"
• "Must be confident and a damn good flirt"
• "I don't care about your gender as long as you're into men — otherwise I think this will all be too abstract"
• "Must have at least one long-term relationship (over a year) under your belt, so that you have a sense of what an emotionally available man presents like"

To apply, she said, share a resume, a note about what interests you about the gig and "a brief description of YOUR dream man." She'd pay $25 per hour or a flat rate per date you arranged.

Getting paid to 'help a badass lady find some man gold'

I couldn't believe it. This gig actually sounded fun.

I'm a professional wordsmith, I said in the email I immediately sent, so I was capable of "writing goodly." I've been dabbling with dating apps for years so have a handle on how those things work. My dream man is kind of elusive but loosely he's kind, intelligent and quietly confident, perhaps Andrew Garfield.

I could fully relate to her dating app woes. "If I can help a badass lady find some man gold," I wrote, "that feels like a pretty major win."

Within hours, I got a response: "Hey Gili, let's talk."

We Skyped the following day then met up for drinks at a wine bar in Brooklyn to hammer out details. I'd swipe and text on her behalf using her profiles on apps like Bumble and OkCupid. She'd give final approval, and then I'd set up the dates.

Pay was $100 upfront then $150 for each date.

'Dreams DO come true'

The gig didn't last long. Over the next three or so weeks, I swiped on and chatted up likely dozens of guys at night and on lunch breaks. I must have spent at least 20 hours doing this.

It felt kind of bizarre. When I was texting as me, I always felt comfortable being a goof. But I was pretending to be someone else and didn't want to say anything that wasn't authentic. I found myself regularly turning down any natural sass.

The other challenge was that given the fact that my client was paying $150 per date, she was picky. There was plenty of interest on the guys' parts. But there was often a reason she wouldn't move forward. Some dudes were a little too forward. Some a little too old. Some were too reminiscent of exes.

Eventually I told her that, though I understood why she was picky, it meant I did hours of work without getting paid. And the gig sort of fizzled from there. Altogether, all I made was that initial $100.

We lost touch over the pandemic, but I reached out recently to see how she's doing. Turns out she reconnected with and has been happily dating someone she met on Tinder before she and I even embarked on our personal Cyrano de Bergerac.

"Dreams DO come true," she said.

As for my own 2019 objective, through various side gigs and vigorous saving, I paid off the $1,293 by fall.

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