Matchmaking For Hire: The Online Dating Side Hustle That Went Nowhere — 'I Couldn't Believe It'

Zinger Key Points
  • One woman posted an ad on Craigslist offering to pay someone $25 an hour to set up dates.
  • An editor looking for a second income stream decided to take on the matchmaking challenge. 

Trying to find love in an increasingly digital world has led many to experiment with online dating, but endless scrolling of profiles and pictures can leave some feeling hopeless.

One woman decided to post an ad on Craigslist offering to pay someone to pretend to be her and set up dates. An editor looking for a second income stream decided to take on the matchmaking challenge

What To Know: In 2019, Gili Malinsky was making $58,000 per year working as an editor for a media company in New York. She had several thousand dollars in student loan debt and was up against a large tax bill, so she started looking for a second source of income

It wasn’t long before she stumbled upon a Craigslist ad, unlike anything she had ever seen before.

It said, “Help me find love online,” Mailnsky recalled in a piece she wrote for CNBC’s Make It. 

“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,” the description of the ad read. 

Check This Out: From Lineman To ‘Laundromat Millionaire’: How Craigslist And Clothes Cleaning Changed This Man’s Life

The woman was offering $25 per hour or a flat rate per date if that was preferred, and that was enough for Malinsky to respond to the ad.

“I couldn't believe it. This gig actually sounded fun,” she said. 

They set up a Skype call and then met up for drinks to talk details the following day. Malinksy planned to search for quality date candidates on apps like Bumble Inc BMBL and IAC Inc’s IAC OkCupid, chat with the guys and hope to set up dates. 

She was offered an upfront payment of $100, and they agreed that she would be paid $150 for each date she successfully planned. 

Everything went wrong from there, for Malinsky anyway. She spent at least 20 hours chatting with dozens of guys over the next three weeks and found it “bizarre” to pose as someone else. 

The woman who posted the ad ended up being very picky — so selective that she didn’t actually agree to go on any dates. Malinksy would filter through guys to find good options, but the woman she was pretending to be would find something wrong with all of them. 

In the end, Malinksy never saw another dime beyond the initial $100 she was paid to start her search efforts.

She did reach back out to the woman who posted the ad to see how she was doing after some time had passed and it turned out that she had reconnected with one of her old matches on Match Group Inc’s MTCH Tinder. 

“Dreams DO come true,” she told Malinksy. 

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Photo: Adrian from Pixabay.

Some elements of this story were previously reported by Benzinga and it has been updated.

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