They eventually became a couple and got engaged. Although they never made it through the isle, their relationship as friends would carry on.

D’Souza was described as “political pundit, writer, documentary-film maker, and onetime wunderkind of the intellectual elite” i.
Dating history
“Dinesh is simply one of the finest human beings I have ever met,” Ingraham wrote in her
“His generosity of spirit, philanthropy, keen sense of compassion and devotion to country are what I hope my own exhibit when they mature into adults. Until this recent unfortunate chapter, his life has been the quintessential immigrant success story. I understand the facts of his case and that the court takes his plea very seriously. I simply urge, during this sentencing phase, that you consider his life in its totality — his contributions, humility and compassion.”
In the 1990s, as Ingraham’s TV career began to pick up speed, her love life attracted more publicity and attention.
In 2008, reported that Ingraham dated political pundit Keith Olbermann “briefly a decade ago.” Their political views were polar opposite. That, however, wasn’t the reason to why the couple went separate ways, according to Olbermann.
He said: “There were a few problems. There were a few things that I could see were going to be impediments. Oddly, they were not political things.”

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