In 2005, she announced her engagement to businessman James V. Reyes.
Reyes and Ingraham supposedly met after being set up on a blind date.
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.
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.

“Dinesh is simply one of the finest human beings I have ever met,” she penned.
She also got into a short-lived relationship with liberal commentator Keith Olbermann around the same time.
However, he admitted that he saw red flags from the start.

Ingraham and Olbermann also don’t appear to be on good terms.
IT’S A BIT.
For God’s sake, trust me on this," Olbermann wrote.
“I dated her.
She thinks she’s funny, and funny in this way.”
He alsoquippedIngraham couldn’t do anything as well as lying, and alsoreasonedthat she was cruel but smart.