Following the Royal Family's annual Easter Sunday service in Windsor in 2023, the former prince was captured holding a gate open for the clergy, Princess Anne and Sarah Ferguson.
When Peter Phillips and his bride-to-be, Harriet Spearling, arrived at the Cheltenham Festival for a day of good old-fashioned fun last month, the awkward happened.
During her two-hour visit to the Salisbury Plain Training Area, Anne spoke with troops about their extensive four-week training programme while also getting stuck in with exercises.
As members of the Royal Family gathered outside of St George's Chapel in 2025, eagle-eyed onlookers noted a rare interaction between Andrew and Vice Admiral Sir Tim Laurence.
Princess Anne has built a reputation for tastefully redeploying outfits years apart, with the habit earning her the unofficial title 'Queen of Royal Recycling'.
The Princess Royal, who is patron of the Scottish Rugby Union (SRU), was captured warmly embracing Sione Tuipulotu following Scotland's final Six Nations fixture against Ireland on March 14.