Charles Spencer is custodian of his family home, Althorp, where he and his sisters, including the late Princess Diana, grew up.
Earlier in the week, on the most recent episode of the podcast he co-hosts, Rabbit Hole Detectives, he revealed that pop superstar Madonna and her then-fiancé, director Guy Ritchie, were considering getting married on the estate.
During the course of their "surreal" conversation, the singer also gave some family advice to the Earl.
Speaking to his fellow presenters, Richard Coles and Dr Cat Jarman, Charles said that after overcoming his initial shock and having a chat about the star's potential wedding arrangements, she asked him how he was.
"At the end she just said, 'And how are you doing?' I said, 'Fine thanks, how about you?' and she said, 'Well, I'd recommend you don't give birth and bring out an album in the same month'".
"Good advice," Richard chimed in, to which Charles joked: "I have stuck by it religiously". The hitmaker and her film director beau ended up not getting married at Althorp in the end and instead headed to Scotland to tie the knot, marrying at Skibo Castle on 22 December 2000.
They were married for eight years before they separated and share sons Rocco, now 23 and David, 17. Reflecting on their marriage, the filmmaker later said: "I love the kids that came out of it, and I could see no other route to take. But you move on, don't you?"
Althorp House is now a wedding venue that is open to the public, and it offers couples the chance to have a civil ceremony in one of the five State Rooms: the Picture Gallery, the State Dining Room, the Great Room, the Saloon or the Marlborough Room.
Charles revealed another insight into the property on Saturday when he shared a stunning portrait on display, which was photo of his great-grandmother, Margaret, back in her family home in Dallington House, Northampton.
In the sepia-toned photo, Margaret was sitting at a desk, although her outfit hinted that she was due at a major event as she could not have been more glammed up.
She sat in an elegant floor-skimming gown while wearing a hat that wouldn't have looked out of place at Royal Ascot. Behind her were several family portraits of her own children, which included Charles' grandfather, Jack, and the Earl revealed that he still had three of those photos.
Captioning the image, he explained: "My great-grandmother Margaret Spencer (née Baring), at her desk in her sitting room at Dallington House, Northampton, in c. 1900. I still have the portraits of three of her children that hang, here, above her fireplace. (The one to the left is of my grandfather, Jack, in a sailor suit.)"
Fans were quick to react, with many completely enamoured with Margaret's choice of headwear. "Was it the custom then to wear a hat indoors?" one wondered.
A second enthused: "How wonderful! And to think she wore her hat while writing to her morning correspondence. Charming," while a third joked: "I hope you wear such a splendid hat when at your desk writing."