I like to believe that, if I'd been in the right place at the right time, I could have become the Duchess of Sussex. But being in the right place at the right time isn't always enough — even if you are the daughter of the 43rd U.S. president. Apparently, as reported by PEOPLE, Jenna Bush Hager tried setting up her sister with Prince Harry, but the plan was foiled — or so she believes — by a pair of sunglasses.
On the July 26 episode of Today with Hoda & Jenna, the co-host revealed that her sunglasses may have been the reason that her matchmaking attempt between the Duke of Sussex and her fraternal twin sister, Barbara, didn't go quite as planned. Jenna was hoping to shoot her shot on behalf of her then-single sister while interviewing the handsome (and also then-single) Prince during the 2016 Invictus Games in Orlando, Florida, but it happened to be a particularly sunny day. Prince Harry reportedly suggested they both wear sunglasses to keep from squinting (though TBH, he'd look cute even with his eyes half-closed). According to Jenna, this lack of direct eye contact created a "barrier" between them, which prevented her from really selling Harry on the idea of a date with her sister.
“He has really beautiful light eyes, which are sensitive to the sun," Jenna explained during the show. "I know because my daughters have light eyes. Prince Harry was like, 'We have to wear sunglasses, don’t you think?' I was like, 'Well, if he says it’s OK!'" I mean, you don't say 'no' to a prince, right?
But Jenna regretted this decision when it came time for her to mention her sister — which Barbara had no idea about ahead of time. While talking about his love life and whether he ever planned on having children, Harry laughed and pointed out that he didn't even have a girlfriend. That's where Jenna saw her opening. “I have a single sister," she told him, "and she feels the same way. Listen, she’s available. She’s going to kill me.”
Harry politely suggested they discuss a potential date further once they got off air, and Jenna even told the Prince that she would give him her sister's phone number. Of course, only two months later, Harry met his future wife, Meghan Markle, on a blind date, and any chance of him arranging a date with Barbara went out the window.
Even though Barbara was totally "humiliated" by the entire incident, Jenna told Fox News soon after the 2016 Invictus Games interview that she stood by her decision to take a chance, "...because of course, [Barbara] should be a princess.” She later added, "Come on! There’s all those palaces we could borrow!” You make a good point, Jenna.
Though this wasn't Jenna's first time playing matchmaker for her sister, this was the first time she ever tried to hook her sister up with a Prince. Seeing as Barbara married screenwriter Craig Coyne in 2018, I'd say that things worked out quite well for her, but still. You definitely have to give Jenna props for trying to get her sister a crown when she had the chance.