While speaking with the BBC about what it was like being the Princess of Wales, Diana explained that her role was a "challenge".
While the royal didn't delve too far into the specific "challenges" involved with her duties, Meghan laid it all out on the table.
"My understanding and my experience of the past four years is, it’s nothing like what it looks like." the former duchess told Oprah. "And I . . . and I remember so often people within The Firm would say, ‘Well, you can’t do this because it’ll look like that. You can’t’."
The former actress also revealed she was "silenced" by the royal family and felt very "isolated" - a sentiment which Diana certainly expressed in her own interview.
After Bashir asked the princess whether she though she was "left largely to cope with (her) new status on (her) own", Diana replied, "Yes I do, on reflection.... It was isolating, but it was also a situation where you couldn't indulge in feeling sorry for yourself: you had to either sink or swim. And you had to learn that very fast."
Meghan herself dived into the more harrowing aspects of her own feelings of isolation, claiming The Firm didn't help her when she needed it most.
The former duchess opened up to the TV presenter about her darkest times in the public eye, explaining there was a time when she "didn't want to be alive any more". After Meghan told the Palace about her mental struggle, she claimed the institution did nothing to help her.
"This was emails and begging for help, saying very specifically, ‘I am concerned for my mental welfare’. And people going, ‘Oh, yes, yes, it’s disproportionately terrible what we see out there to anyone else’. But nothing was ever done, so we had to find a solution." Meghan revealed.
Similarly, Princess Diana also spoke about her own mental health battles, revealing she had dealt with post-natal depression and self-harmed in the past.
Unlike Meghan, when it came to The Firm, Diana kept her internal battle just that - internal. But the princess did explain how her position in the monarchy prevented her from getting any better.
Indeed, when Bashir asked the royal if she felt she "had to maintain the public image of a successful Princess of Wales" through her mental struggles, the princess replied with "Yes I did, yes I did."
This connection to Diana was also not lost on Meghan, who revealed that it was one of her late mother-in-law's friends who eventually gave her the help she so desperately needed.
"One of the people that I reached out to, who’s continued to be a friend and confidant, was one of my husband’s mum’s best friends, one of Diana’s best friends. Because it’s, like, who else could understand what’s . . .what it’s actually like on the inside?" the former Suits actress explained.
And speaking of understanding what it's like, both Diana and Meghan were, and are, the subject of intense media coverage - a topic that both of the former royals spoke about in their respective interviews.
In the years leading up to her interview, Diana was still the wife to the next heir Charles; this position, the royal explained, made the media extremely obsessed with everything the future Queen Consort was doing.
"We had the media, who were completely fascinated by everything we (herself and Charles) did." Diana told Bashir.
"And it was difficult to share that load, because I was the one who was always pitched out front, whether it was my clothes, what I said, what my hair was doing, everything - which was a pretty dull subject, actually, and it's been exhausted over the years."
Like her late mother-in-law, Meghan Markle remains a constant fascination of the media's - a topic that Oprah was hell-bent on discussing with her friend.
"Soon after your marriage, the tabloids started offering stories that painted a not-so-flattering picture of you in your new world. There were rumours about you being ‘Hurricane Meghan’." Oprah said to the former actress.
The pair went on to discuss the "hero and villain" narrative painted around Meghan and her sister-in-law Kate Middleton. When Oprah asked why Meghan was held to a different standard than Kate, the former duchess replied "I can see now what layers were at play".
The "layers" Meghan was speaking of were admittedly very different to Diana's experience, as they pertain to race.
Meghan Markle is the first mixed-race person to marry into the monarchy and both herself and Oprah discussed how this fact influenced the media's coverage of her, as well as, according to Meghan, some comments made by the royal family themselves.
While both Diana and Meghan have had their own specific battles as members of the royal family, similarities between their experiences can be drawn, not only from their interviews, but from the way they acted throughout their time in the public eye.
From breaking protocol to being overwhelmingly candid about their personal lives, these two royal-in-laws have proven that the age-old "never complain, never explain" ethos is not for them; they'd much prefer to draw back that Buckingham Palace curtain and let people know what it's really like on the inside.