Stern Show Looks Back at Staffers Who Struggled to Make a Celebrity Love Connection

From Bravo host Andy Cohen to reality star Khlow Kardashian, Howard relives years worth of blown opportunities

November 9, 2021

There was a time when Hollywood’s most renowned beauties preferred rock frontmen and perfectly chiseled movie stars, but these days everyone from “Saturday Night Live’s” Pete Davidson to “Saturday Night Live’s” Colin Jost seems to be coupled up with an A-list actress or pop star. With that in mind on Monday, Howard looked back at several Stern Show staffers who’ve struggled to make a celebrity love connection of their own.

“I try with my guys,” Howard began, recalling the time he encouraged reality star Khloe Kardashian to hold staffer JD Harmeyer’s hand as she walked out of the building after her 2016 Stern Show interview. “JD is holding her hand the whole time [and] not one fucking newspaper reported it,” he continued. “The press looked at JD and they went, ‘There’s no fucking way.’”

“She even hugged me,” JD lamented.

“Then I tried to set you up with Eliot Spitzer’s gal, Ashley Dupre, but you blew that, too,” Howard reminded his staffer.

“Yeah, I don’t know what it was about me that she wasn’t attracted to,” JD said.

More recently, Howard scored staffer Chris Wilding a date with Bravo star Andy Cohen. “He totally blew it,” Howard recalled of the duo’s one-and-done outing. “Well, no, he didn’t blow it.”

“Andy opened our date saying this wasn’t a date, so I didn’t think there was much opportunity there,” Chris said, later adding, “I would’ve blown Andy!”

Even executive producer Gary Dell’Abate has long sworn he had a shot with Jennifer Aniston back before she became a superstar. But Howard didn’t buy that for a second. “She married Brad Pitt. She married Justin Theroux. She only dates hot dudes,” he said, adding, “[Gary] had a pretty inflated view of himself.”

Stern Show co-host Robin Quivers, on the other hand, was the exception who proved the rule. She had famously turned down huge celebs ranging from champion Joe Frazier to late E-Street Band saxophonist Clarence Clemons.

“He came on to me,” Robin remembered of her on-air encounter with Clemons, who in a clip played on Monday implored Mrs. Ophelia to take a steamy bath while listening to his records.

Smokin’ Joe, meanwhile, took a different approach. He serenaded Robin in the studio with a sultry version of Frank Sinatra’s “My Way.” “Joe Frazier was in love with you. I think you could’ve been Mrs. Joe Frazier,” Howard suggested before playing a clip of him crooning.

As Robin recalled it, however, she eventually broke the boxing legend’s heart: “He walked into my little anteroom that was outside my studio and there was a huge picture of Muhammad Ali. He was like, ‘Oh my god, Robin—I thought you were my fan.’ I was like, ‘Joe, I love you!’”

“You’ve been courted by the best of the best,” Howard said.

You Give us your email Address we'll give you even more howard!

By signing up, I agree to receive newsletters and marketing emails from the Howard Stern Show and accept the Terms of Use and Privacy Policy