Howard Stern has this unparalleled ability to make seemingly normal individuals massive stars. He doesn't do it in the way a show like American Idol promises. He's far more authentic about it and it's always on his terms. Specifically, Howard is able to make his staffers nearly as beloved as he is. Fans of The Howard Stern Show tune in to hear the exploits of his staffers just as much as Howard himself. But while Howard's staffers have massive fanbases, they don't seem to have the same kind of pull with celebrities.
In a recent discussion on the SiriusXM radio show, Howard compared his staffers' celebrity dating success rate to that of the stars of Saturday Night Live. Pete Davidson, Colin Jost, and other stars of SNL have met some of their most famous romantic partners when they guest-starred on the sketch show. The same can't be said for his staffers when single celebrities have appeared on Howard's show. Even still, some of Howard's staffers have been trying to hook up with some of his hottest guests...
Producer Gary 'Ba Ba Booey' Dell'Abate Tried To Date Jennifer Aniston
Perhaps the most famous example of a Stern Show staffer trying to hook up with a celebrity is Gary Dell'Abate's attempt to win over Jennifer Aniston. Among Stern Show fans, this story is legendary. Long before Jennifer was a massive sitcom star she was simply trying to make it as an actor. This meant taking a job as a model for Nutrisystem and appearing on The Howard Stern Show in the early 1990s when he was at the height of his shock jock phase.
Years after her brief appearance, producer Gary 'Ba Ba Booey' Dell'Abate somewhat foolishly told Howard and his colleagues that he believes he could have "gotten" Jennifer. Behind the scenes, Gary thought that Jennifer was flirting with him. Had he not been involved with someone at the time, Gary would have made a move and successfully scored a date with her... or so he thinks...
Given the fact that Gary has always been a punching bag on the show due to his looks, this anecdote has become a running gag. Howard and all of Gary's colleagues simply believe he was foolish to ever imagine a woman like Jennifer would go for a guy like him. According to Jennifer, who has since appeared on the show and is actually friends with Howard, she has no recollection of any flirtation between her and the producer.
JD Harmeyer Tried To Date Khloe Kardashian, Ashley Dupre, And Katrina Bowden
For the first few years of JD Harmeyer's time on The Howard Stern Show, he was the nerdy virgin. A lovable punching bag for the rest of the staffers. While Howard has always had fun teasing "mush-mouth" JD, he also claims to see him as a son. Nowadays, JD is a married man and lives a much more normal life than his early days on The Stern Show when Howard was constantly trying to set him up.
During his single years, JD admitted to trying to date numerous celebrities. During a Howard Stern Wrap-Up Show interview, JD admitted to basically stalking 30 Rock star Katrina Bowden in a New York subway. Addionally, he also flirted with model Adrianne Curry and actually went out with former NY Governor Eliot Spitzer's call-girl, journalist Ashley Dupre. In fact, JD may have been a bit too obsessed with Ashley after she told him that she "just wanted to be friends".
In 2016, after an interview on the show, Howard tried to fix JD up with Khloe Kardashian in order to start dating rumors. The reality star was totally game for the rumors and even allowed JD to hold her hand while walking her out of the SiriusXM building to meet the press. To try and seal the deal, the two hugged, but the press clearly didn't believe that Khloe and JD could ever be a thing. And while JD was interested, it was clearly just a stunt on Khloe's part.
Howard Tried To Set-Up Chris Wilding With Andy Cohen And Kate Beckinsale's Assistant
Stern Show staffers aren't just a bunch of heterosexuals. There is some diversity in the ranks, and that includes Chris Wilding. While Chris Wilding's private life is a magnet for bits on the show, Howard tried to step things up a notch when he got Bravo's Andy Cohen to flirt with Chris on air. While Chris was totally game to go on a date with Andy, the Real Housewives creator ended up ghosting him behind the scenes.
Aside from Andy Cohen, Howard has recently tried to set up Chris with Kate Beckinsale's assistant. Even though both Kate and her assistant were down, it seems that Chris is too infatuated with his real-life boyfriend.
Ralph Cirella Actually Dated Star Trek Actor Terry Farrell And Robin Quivers Went Out With Dennis Rodman
Howard's right-hand woman and co-host Robin Quivers did actually go out with controversial basketball star Dennis Rodman. While Dennis was reportedly totally interested in being with Robin, she had no interest in him after the first date. Unlike the other staffers on this list, a few other celebrities actually made some efforts to date Robin. This includes Joe Frazier, Lenny Dykstra, and musician Clarence Clemons. All of which Robin wasn't attracted to... Jake Gyllenhaal, on the other hand...
Yes, Robin really wanted to date Jake Gyllenhaal and shamelessly flirted with him on-air during both of his Stern Show interviews. But it seems Jake's heart is tied up elsewhere.
The only Stern Show staffer to successfully date a celebrity is Howard's stylist, Ralph Cirella. While Ralph may be one of the least likely staffers to maintain a successful romantic relationship, he actually dated Star Trek: Deep Space Nine star Terry Farrell. Ralph's surprising privacy regarding his brief connection with Terry in the '90s proves something legitimate went on. This includes him moving out to California to be with her.
Even though most Howard's staffers haven't exactly been the luckiest while trying to date celebrities, their failed attempts make for great bits on the show.
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