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Jacobson made frequent guest appearances on "Livin' Large with Geoff Pinkus" on WIND (AM) and worked as a traffic and news reporter for WLS (AM) from 2008 to 2010, beginning on the Roe Conn Show, and then moving to The Mancow and Cassidy show.She became co-host with Big John Howell on WIND (AM) on March 24, 2010. But we also just kept being, like, ‘But you miss New York, right? The streets and avenues are veins, and all the people and the cars are blood pumping through it constantly, with a rhythm.They credit Amy Poehler, executive producer of the show, for being able to be so sexually adventurous in the show. We just wanted to make sure it was very clear we were not, like, ‘Pegging’s crazy!Jacobson had been covering the story of Lisa Stebic's unexplained disappearance.On July 10, 2007, Jacobson and WMAQ-TV negotiated her exit, following an investigation by the station.
But the two days they spent with New York — at dinner at ABC Kitchen, the Cut’s fashion party at the Gramercy Park Hotel, and coffee in Greenpoint — yielded far more goodness, laughs, and stray observations than could fit in any one magazine feature. Abbi’s roommate’s terrible boyfriend who never leaves their apartment, played by John Gemberling, is named after Abbi’s best friend, Jess Bevers, who just moved to Belgium.
On July 7, 2008, the Chicago Sun-Times reported "On Monday, Jacobson filed a multimillion-dollar lawsuit against CBS-owned WBBM-TV-Channel 2 for airing the tape of her at the home of Craig Stebic, the southwest suburban Plainfield man whose estranged wife, Lisa, has been missing since April 2007." That lawsuit was dismissed with prejudice on July 5, 2013, after the court ruled Jacobson failed to show CBS fabricated unfavorable content about her, the judge finding that the critical comments and other material in the CBS piece were "constitutionally protected expressions of opinion," or based on facts.
Jacobson's attorney indicated that she will appeal the dismissal of the lawsuit.
Like, why would I not be open to that—because it has some sort of gay connotation? As we move forward, we’re going to do more of that.
’ I just sat back, and I was like, When we were pitching, Amy was like, “Everyone under 30 is gay,” but this was, like, five years ago. Because in seasons 1 and 2, we didn’t really have that. I think it’s part of that fluidity—it’s OK to feel that way about your friends and it’s OK to have that energy also.
“Yeah, people think that, like, those are paid sponsorships and it’s not,” says Abbi.