Guilfoyle's 2017 departure from Fox News was due to alleged sexual harassment on her part.Fox News later reached a settlement of at least $4 million with Guilfoyle's accuser.The assistant alleged that Guilfoyle frequently displayed herself naked, showed photographs of the genitalia of men she had sex with, and required her to sleep over at Guilfoyle's apartment.The New Yorker independently verified several of the assistant's allegations.
Guilfoyle has also faced separate allegations of making sexually explicit comments at fundraisers. In 2004, it was reported that in speaking on behalf of then-husband, Gavin Newsom, at the Empire State Pride Agenda gay rights fundraiser, Guilfoyle boasted about his attractiveness and large penis size, and implied (through innuendo and pantomiming) that she was talented at providing oral sex. This was treated in San Francisco as a political controversy. Guilfoyle subsequently denied that her arm gestures were meant to be a sexually explicit pantomime.
In November 2020, Politico's reporting alleged that Guilfoyle had engaged in sexually explicit conversations during private Trump fundraisers that had made some attendees uncomfortable, including explicit conversations involving Trump Jr., disclosing at a fall 2018 fundraiser that Trump Jr. liked her to cosplay as a Dallas Cowboys cheerleader, making an offer at a December 2019 fundraiser to personally reward the event's top contributor with a lap dance, and offering at a 2020 fundraiser to host a hot tub party for its top contributor.