She’s finding love in a hopeless place.
After relocating to Midtown Manhattan from a small town near Indianapolis last November, something quickly became apparent to content creator Sydney Street, after waving off a string of wannabe playboys and raging party animals at nightclubs and bars — encountering your happily-ever-after in the Big Apple is about as likely as spotting an unclaimed $100 bill on a Midtown sidewalk.
Street’s anecdotal experience on the local dating scene is backed up by serious research — the country’s largest city was also ranked as one of the worst for young singles on the make in a November 2022 study by WalletHub. But rather than admit defeat, the demure, Gen Z brunette, who tends to favor real-time connections over swiping sprees on the usual dating apps, decided to fight back.
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“Dating in the city is really difficult for people my age — I had the idea to set [them] up,” Street, 24, told The Post.
Last month, the hopeful romantic launched a one-Cupid campaign to turn the dating scene in her adopted city on its head. Armed with her iPhone, the modern-day Yente hit the streets and began curating romantic matches between unsuspecting strangers in Washington Square Park, where throngs of students tend to congregate around the iconic fountain.
“I’ll go up to someone and ask if they’re single, who they’re into dating and to point out anyone in the park who catches their eye,” she said. “Then I ask the other person if they’re single and if they’d be willing to take him or her on a date, and I offer to pay for it.”
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If both daters are up for it, Street, the head of social media for dating app Schmooze, where you swipe through someone’s funny memes rather than stagnant selfies, will Venmo one of the pair $50 for the outing.
After introducing NYU undergrads Ayden Chacko and Leigh Wolberger Moully, both 19, Monday, she shelled out the ducats for the date night they’ve planned to spend in Brooklyn over the weekend.
“It usually takes me about 10 to 15 minutes to find a single person and connect them with someone they’re interested in at the park,” Street told The Post, adding that she’s already made five successful pairings, three same-sex couples and two straight couples, in just a few weeks. She partially credits her wing-woman triumphs to her offer to treat the twosome.
“A lot of people really love the idea that I’m footing the bill,” she laughed, “but one guy did say $50 was way too much for a date.”
Videos of the mobile matchmaker have gone viral on the app’s social media platforms. Footage of Street’s quest to secure love for a twenty-something named Kylie has earned more than 5.2 million views on TikTok. After failing to find the blond’s beau in a hipster skateboarder who turned out to be 16, or a handsome guy on a bench who identified as gay, Street managed to match her with a mustachioed hunk named Edon.
In a separate post with over half a million views, Street almost immediately formed a love connection between a belle named Natasha and an inamorata in red shoes named Jara. The pair’s chemistry is apparent as they wind up sitting side-by-side to discuss their near-future plans together.
Not all of Street’s connections lead to dates, but she’s not giving up.
For Jacke Colquitt, 25, the budding pro’s crack at scoring him a date for Valentine’s Day turned out to be a swing and a miss.
“I randomly went to the park Sunday, and Sydney approached me, asking if I was down to let her help me make a real-life, in-person match,” Colquitt, a mental healthcare administrator from Crown Heights, told The Post. “I thought it was so cool — most of my dating experience has been online.”
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And although Street wasn’t able to land him a mate after propositioning “eight or nine” people — many of whom, Colquitt says, were either tourists or already in relationships — he’d be glad to give the romance broker another shot at finding his main squeeze.
“I’d definitely let her help me meet someone again,” Colquitt confirmed. “There’s nothing to lose and everything to gain.”
And Street, who’s been hailed the “Washington Square Park Cupid” by members of her digital fanbase, is happy to be of service.
“It feels good to know that I’m making a positive impact on people’s lives,” she said, admitting that lately, she’s been wondering if it isn’t time to ask a stranger in the park to go out on a date with her.
“Valentine’s Day is just around the corner,” she said. “It might not be a bad idea to help myself.”