Three years ago Rob asked Olivia Culpo whether or not she thought it was fair for transgender women to compete in the pageant.
While the Miss USA pageant has often been targeted for by some for its perceived sexism, the beauty competition has actually shown that it can be rather progressive.
Since 2011, they are the only pageant system that welcomes transgender contestants and that issue was brought into the spot light in 2012 when former reality TV star Robert Kardashian -- step-son of Caitlyn Jenner -- asked about transgender women competing in the pageant during the Q&A portion of the evening.
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"Would you feel it would be fair that a transgender woman wins the Miss USA title over a natural-born woman?" Rob asked Miss Rhode Island Olivia Culpo.
While the question itself might not seem all that enlightened -- considering the use of the term "natural-born woman," which many consider an offensive term, preferring instead the term "cisgender woman" -- Culpo was able to deliver a well-considered response.
"I do think that that would be fair," Culpo said, after carefully choosing the language to use in her answer. "But I can understand that people would be a little apprehensive to take that road because there is a tradition of natural-born women but today where there's so many surgeries and so many people out there who have a need to change for a happier life, I do accept that, because I believe it's a free country."
Culpo's thoughtful response drew cheers from the audience, and she later went on to claim the title of 2012's Miss USA.
Now, three years later, Miss USA is addressing the issue of transgender women in America by reaching out to Caitlyn to be a judge for this year's pageant.
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On Thursday, a rep for the Miss USA organization told ET that they are reaching out to Jenner to make her an offer in the hopes that the former Olympian would serve as a judge for their July 12 event.
"While she is not yet confirmed to judge, the organization would indeed love to have her," the Miss USA spokesperson explained to ET.
Jenner's Vanity Fair cover has taken the world by storm, and Caitlyn herself has become the current face of many conversations about transgender women in America. For more on Caitlyn's celebrated cover appearance, check out the video below.
