Meet The Men Fox News' Laura Ingraham Almost Married

Although Fox News host Laura Ingraham has never walked down the aisle, she got pretty close twice in her life. In 2005, she announced her engagement to businessman James V. Reyes. Reyes and Ingraham supposedly met after being set up on a blind date. However, the couple never had their nuptials, possibly because the presenter was diagnosed with breast cancer around the time. In April, she expressed her gratitude for her fiance, but they split up soon after. 

Ingraham has stressed the importance of a traditional family with a masculine and a feminine figure. During her show "The Ingraham Angle," she said that corporations were trying to damage traditional ideals of masculinity by promoting (what was by her definition) feminine clothing like figure-hugging jeans. In another episode, she doubled down on her sentiments by saying, "Women want men to be men." she added. "All the pajama boy fans are shocked that young men are flocking to non-effeminate men like Jordan Peterson and they're especially furious that millions are tuning in to listen to manly men like Joe Rogan," (via Newsweek). Her statements reminded us of things women think they want in a man — but don't, as Ingraham's dating history doesn't seem to be chock-full of the alpha males she wants to see more of in the world.

Laura Ingraham's paths crossed with conservator commentator Dinesh D'Souza when they were students at Dartmouth in the 80's. They reportedly sparked a conversation while working on the college newspaper, "The Dartmouth Review" and started dating shortly after. It seems like they struck up a deep connection because D'Souza put a ring on it, but they didn't follow through with their plans. D'Souza went on to have a decade-long marriage with Dixie Brubaker, which ended in 2012. After that, he found love with Deborah Fancher, and they reportedly tied the knot in 2016. 

Despite the serious nature of D'Souza and Ingraham's former relationship, the exes don't appear to have any bad blood. When the author pleaded guilty to breaking election law by committing campaign fraud in 2014, Ingraham wrote a letter to the judge presiding over the case to portray him in a better light. According to Politico, her heartfelt note explained how D'Souza paved his own path in the U.S. after moving as an exchange student with barely any money. She credited the "2000 Mules" filmmaker with nurturing her journalistic career's start by teaching her how to craft engaging news, find reliable sources, and always speak her truth. "Dinesh is simply one of the finest human beings I have ever met," she penned. "His generosity of spirit, philanthropy, keen sense of compassion, and devotion to the country are what I hope my own children exhibit when they mature into adults."

It appears that Laura Ingraham didn't entirely take Dinesh D'Souza's advice of staying true to herself and to her principles, because she went on to date two democrats. She sparked dating rumors with democratic senate member Robert Torricelli around 1999, but neither has publicly commented on their supposed romance. She also got into a short-lived relationship with liberal commentator Keith Olbermann around the same time. 

Though the two have remained tight-lipped about the start of their romance, Olbermann told The New Yorker that it actually didn't end due to their vastly different political opinions. However, he admitted that he saw red flags from the start. Ingraham and Olbermann also don't appear to be on good terms. After the sports commentator made a controversial statement about the United States' activities during the Iraq war, he received criticisms from several conservatives, including Ingraham, who said that she didn't recognize the man he had become. 

When a clip of a confused Ingraham arguing with author Raymond Arroyo went viral, Olbermann weighed in on the issue through X, formerly known as Twitter. "JESUS. IT'S A BIT. For God's sake, trust me on this," Olbermann wrote. "I dated her. I went through three evenings of this kind of humor, some of it far more agonizingly long than this. She thinks she's funny, and funny in this way." He also quipped Ingraham couldn't do anything as well as lying, and also reasoned that she was cruel but smart. Even her brother, whom Ingraham has a messy relationship with, shares the same sentiments as Olbermann regarding Laura's meanness.