- In 2015, Yossi Rosenberg was named "NYC's most desperate single man."
- He said he spent 20 years going on "hundreds" of dates before meeting his new wife.
- Ivy Branin, who married Rosenberg last month, said she was smitten by his offbeat personality.
On June 28, in front of 170 guests on a blistering summer day in Brooklyn, New York, Rabbi Yakov Bankhalter officiated a wedding under the chuppah for Ivy Branin and Yossi Rosenberg.
Leaving guests to wonder if this was a wedding ceremony or a roast, the rabbi told the crowd: "In 2015, there was an article about Yossi Rosenberg that said he was the most desperate bachelor in all of Manhattan." Met with roaring laughter, he continued, "We need to update that article — that this bachelor is here today with the most incredible woman as his partner."
Back in 2015, Rosenberg was a 35-year-old, down-on-his luck bachelor who lamented being stuck in the friend zone. He tried to woo women by paying for customized videos to ask them out, starring a bizarre cast of characters like a half-naked Brit with a Union Jack flag over his crotch.
The effort earned him the title of "NYC's most desperate single man" from the New York Post, with one object of his affection telling the paper that the video he sent her was "borderline creepy."
After the story ran, the "most undateable" designation followed Rosenberg, a quirky, self-deprecating Boston-area native who works in e-commerce, for years.
"When the story broke, I was the most desperate, single guy," said Rosenberg, now 42. "People who didn't know me probably thought that I was some pathetic loser. Labels stick."
But the story was also a wake-up call: it motivated the "embarrassed" Rosenberg, who'd been on "hundreds" of dates since he was 18, to restrategize. Being stigmatized so publicly "probably affected how I saw myself," he said.
'I wanted to be taken more seriously by women'
A few months after the Post story, Rosenberg made an appearance on the "Steve Harvey Show" for a makeover. He finally had some game — however short-lived. "I changed my look, I reinvented myself," he said.
He then fell in with the Sterling Institute, a personal-growth center for men, participating in weekly group sessions for five years. It helped "empower" him and "overcome the barriers I had," he said. "I was this goofy character, and it made me more Clint Eastwood. I didn't want to be Curly from the Three Stooges or a class clown anymore. I wanted to be taken more seriously, so women would take me more seriously."
On the night Hurricane Ida bore down on New York in September 2021, Rosenberg met Branin, a petite, dark-haired naturopathic doctor who also lived in Brooklyn and shared numerous mutual friends with Rosenberg. She had been out there as well, dating her entire adult life without finding The One.
"People would always say, 'When you meet your person, it's easy,'" said the 42-year-old, admitting she wrote off the advice. "But it's true."
Rosenberg's new wife fell for him, despite his past dud designation
After learning from experience that many of his potential dates did due diligence online, Rosenberg had a preemptive conversation about the article with Branin, mentioning his 15 minutes of fame so she wasn't caught off-guard.
"He got coined the most desperate single man, but I feel like I've been the most desperate single woman for a long time," Branin, who lamented the "terrible" dating climate in New York, joked to Insider. She didn't have to force herself to look past his reputation. "I was still attracted to him."
It was their fourth date that ultimately won her over — a swing dancing class Rosenberg arranged, knowing how much Branin, a skilled dancer, would enjoy it.
Even when he revealed his two left feet, she was improbably smitten. "I've never seen someone dance so poorly in my life — he had no idea what he was doing," she said, noting that he'd also forgotten to put on deodorant that day. "He stunk, but I didn't care. I thought it was the most endearing thing I've ever seen."
"He amazes me ... he's totally, unabashedly himself," Branin said of her new husband's lovable foibles. "I'm grateful that more women didn't give him a chance. I really couldn't ask for more."
Despite the difficulties of shedding the "desperate" label that followed him for years, Rosenberg said meeting his beloved was all worth it.
"I was myself, I didn't do anything differently, and that was enough," he said. "I'm still surprised she appreciates me for myself. Like this person loves me for me? I've been waiting all these years for her."