Inside Former Trump Aide Hope Hicks' History Of Age-Gap Relationships

The dating history of former Donald Trump aide, Hope Hicks, seems to suggest that the apple doesn't fall far from the Trump tree when it comes to being romantically involved with someone 20 years apart from you. The age gap between Hicks and her fiancé Jim Donovan is comparable to Trump and his third wife, Melania Trump. Moreover, the list of Hicks' previous partners indicates a years-long pattern of dating older men.

In May 2024, Page Six confirmed reports that Hicks and the Goldman Sachs vice chairman promoted their five-year relationship while hiking in Italy earlier in the year. Romance rumors between Hicks and Donovan first began circulating in early 2020 as Hicks returned to Washington D.C. after working for Fox News in Los Angeles. The couple was spotted at multiple restaurants around L.A. and D.C., and the Daily Mail reported the duo was "official" by March 2020.

Hicks was 31 and Donovan was 53 when the couple began dating, making their age gap 22 years — just two years shy of the gap between Donald and Melania Trump. Based on Hicks' dating history, that gap is par for the course.

Years before Hope Hicks would accept Jim Donovan's marriage proposal, the former White House communications director was rumored to have an on-and-off relationship with Corey Lewandowski. He was nine years older than Hicks and served as Trump's first campaign manager until the former POTUS fired him in June 2016. While Hicks and Lewandowski never confirmed the fling, it was nevertheless written into perpetuity by journalist Michael Wolff.

According to Wolff's book "Fire and Fury: Inside the Trump White House," Hicks — who was serving as Trump's press secretary at the time — had mentioned her concerns about the media's treatment of Lewandowski to the former president. "You've already done enough for him," Trump allegedly told Hicks (via Newsweek). "You're the best piece of tail he'll ever have." Of course, we should note that this book also implied that Trump had an affair with Nikki Haley, but the former South Carolina governor promptly shut that rumor down.

Wolff's book isn't the only evidence Hicks and Lewandowski dated. In May 2016, Page Six reported that an anonymous witnesses saw Hicks and Lewandowski engaging in a verbal altercation near Park Avenue in Manhattan. "Hope was screaming at Corey, 'I am done with you!' It was ugly," the unnamed source told the outlet.

In 2018, the Daily Mail published steamy photographs of Hope Hicks and former White House staff secretary Rob Porter getting up close and personal in the back of a Washington, D.C. taxi. While the two Donald Trump appointees were closer in age, that didn't stop the couple from becoming the center of controversy after two of Porter's ex-wives accused him of abuse. White House staff initially rallied around Porter, denying the allegations and commending his character.

However, the attempts to put out the flames backfired in February 2018 when CNN reported that Hicks, who was romantically involved with Porter at the time, helped write the official statements defending him. Hicks resigned from the Trump White House shortly thereafter and moved to the West Coast to work for Fox News. According to Page Six, she and Porter stayed together until the final months of 2018.

Four years later, she would find herself in the spotlight again as she testified during Donald Trump's hush money trial in early May 2024. She admitted to the courtroom that she was nervous about taking the stand but spoke highly of Trump. Digital director of Trump's 2016 campaign, Brad Parscale, once told Newsweek that Hicks "loves [Trump] like a father." That sentiment tracked as she reportedly broke into tears while on the witness stand.