Laura Ingraham’s Dating History Includes Alleged Romances with Prominent Men

Laura Ingraham’s dating history includes several politically involved figures, including one former President of the US. Although not married, Ingraham is a doting mother of three.

Political commentator and conservative television host Laura Ingraham is known for her strong opinions and commentary on social and political issues. She has also authored several books about political figures.

Although Ingraham tries to keep her personal life away from her professional one, some fans have taken an interest in her dating history. Interestingly, Ingraham has been linked to several prominent men, including some in government.

Ingraham met fellow political commentator and author Dinesh D’Souza while studying at Dartmouth University. At that time, she made history as the first female editor of Dartmouth Review, where D’Souza also worked.

However, their relationship did not work out. D’Souza went on to date Ann Coulter and Dixie Brubaker, whom he eventually married in 1992. “It was my mission to marry the all-American girl,” D’Souza said.

Nevertheless, Ingraham and D’Souza maintained a good relationship. She came to his defense in 2014 over his finance violation case, in which he pleaded guilty. At that time, Ingraham wrote a letter to the federal judge, vouching for D’Souza. In 2021, he appeared on her program, The Laura Ingraham Show.

Keith Olbermann is another political and sports commentator who briefly entered Ingraham’s romantic life. However, the two reportedly parted ways after Olbermann realized their differences. In 2018, he posted about Ingraham’s commentary toward Lebron James, where she told him to “shut up and dribble.” Olbermann said:

“Laura once told me, proudly, that she hadn’t had to have a ‘real job’ since she washed out of her law firm[ three] years before. She said this in 1998. For 23 years, her entire career has been in the Infotainment business.”

Ingraham also reportedly went on a date with Donald Trump, whom she has known since the ’90s. However, their date did not go well, as she did not like his personality. “He needs two separate cars, one for himself and one for his hair,” she told friends. George Conway also reportedly pursued her to no avail.

Several years ago, at the onset of Lawrence H. Summers’ Presidency at Harvard University, rumors about his relationship with Ingraham swirled on the internet. However, their alleged relationship did not last.

In 2005, Summers announced his engagement to English professor Elisa New. His spokesman revealed their wedding would be intimate, with family and close friends in attendance.

In the same year, news about Ingraham’s cancer diagnosis hit the news. Then 40 years old, she faced the battle head-on and underwent surgery to treat the disease. Ingraham was engaged to Washington DC businessman James V. Reyes at that time. Reyes was then a father of two and a supporter of the Bush administration.

She once claimed the adoption process should not be political as kids should be loved and nurtured and are not commodities to be discussed politically.