Isn’t it every teenager’s fantasy to work a menial service job, hand over an iced latté to your celebrity crush, and subsequently collect their digits for a romantic date? Well, it happened to Rob “Bagel Boy” Camilletti in May 1986. The Queens, NY native was 22 at the time, and Cher – the mononymous uber-celebrity and “original cougar” (according to Vanity Fair, at least) – was out with friends celebrating her 40th birthday when she met the handsome huckster. He gave her his number.

Camilletti was an aspiring actor, but his day job was working at a bagel shop. Cher was taken with him, and the pair began dating. The age gap: 18 years. It wasn’t the generational chasm that proved fatal for them three years later, however. Michael Musto, who reported on the relationship for The Village Voice, explains to InStyle, “I felt that the relationship was doomed because of the imbalance — an accomplished superstar vs. a bagel boy slash wannabe actor — but we all thought he was hot, believe me."

“What the hell could she find interesting about a guy like me?” Camilletti was reported as saying in MacLean’s. “I didn’t admit to myself that I was attracted to her. We’re from totally different worlds.”

“You know, he was making bagels at the time. And I thought, ‘What will my friends say if I go out with him?’ But the more I got to know Robert, the less I cared what anybody thought. He may have talked like one of the Lords of Flatbush, but he had so many great qualities, I couldn’t believe it,” Cher revealed to New Woman magazine in 1988. “I met him in May [1986], and I didn’t fall in love until, well, sometime between Thanksgiving and Christmas."

After they began dating, Camilletti benefited from a bit of favoritism, starring in Cher’s music video for “I Found Someone.” With her encouragement and co-sign, Camilletti landed plum roles in Carnosaur 3: Primal Species, The Perfect Gentleman, Roseanne, and NYPD Blue, among others. Meanwhile, Cher had been lying low in her own career. But 1987 would see the release of The Witches of Eastwick (which she was filming when they met), Suspect, and her Oscar-winning performance in Moonstruck. She would quickly become a bankable, and very successful, actress all her own.

When things got hot and heavy and ‘86 rolled into ‘87, Camilletti moved into Cher’s home. He accompanied her to the Oscars where she took home Best Actress for Moonstruck. The tabloids took aim. Camilletti’s real name was hardly mentioned in reports about Cher — instead he was referred to simply as “Bagel Boy,” despite having left his job.

“They were so mean with Robert — you know, ‘the bagel boy,’” Cher admitted to Parade in 2010.

“The NY press had a field day with the guy,” says AJ Benza, former gossip columnist and host of the podcast Fame is a Bitch, reminiscing about the relationship almost three decades later. “When Cher took home Bagel Boy, it gave all us regular guys hope — if Rob could land that fish, maybe we all could.”

The seams on their relationship finally unraveled when Bagel Boy — frequently hounded by the paparazzi and scrutinized about his blue collar employ — had a run-in with photographer Peter Brandt of Star magazine. Rumor had it that he and Cher were about to get married in a top-secret ceremony, and that Cher was pregnant. Brandt was camped outside of Cher’s home working on that tip in July 1988, and Camilletti crashed into the photographer’s Honda, smashing his car and breaking his camera. Camilletti was arrested and charged with felony assault with a deadly weapon. (Cher posted $2,000 in bail.)

“I know Robert. He is not a violent man. This is not Sean Penn and Madonna,″ Cher said at a press conference following his arrest, referring to Penn’s many documented assaults on the paparazzi. “I’ve been doing this for 25 years, and so I’m pretty much used to having my private life destroyed and lies told about me.”

″It’s something that you pretty much have to get used to,” she continued. “After a while it really bothers you and disrupts your family life. I’m usually pretty good about it.”

“It was sad that Cher had to have a press conference to rail against the media about the whole thing,” Musto adds, looking back. “She was defending her right to do what maturing male stars do all the time, and she shouldn't have had to defend it. The media also made a lot out of Rob's temper, but he was mainly reacting to the scrutiny and derision of the press. Of course, a lot of this is in hindsight because at the time I thought the whole relationship was ridiculous. [Laughs] I've learned to be somewhat less judgy.”

Cher and Camilletti split in 1989, cracking under the intense pressure of the media attention. He has been described by his former girlfriend as her “one true love” in an interview with Woman’s Realm.

Cher and Bagel Boy remain great friends, but he’s since traded the bagel-making and the acting for a career as a pilot, flying celebrities in private jets.

“Old boyfriends make good friends,” Cher told Vanity Fair in 2010. “Robert comes to Christmas dinner. He is a huge pilot. He flies for all the biggest names in this town. He flew me to Jamaica."

#Hollyweird is a bi-weekly column about celebrities' forgotten or buried strange-but-true stories.