Jewellery tends to be the go-to romantic gift, but watches can carry even more meaning. Few things are as personal as the choice of a timepiece. To get it right unaided is a real sign you know someone extremely well. The practical function of a watch dictates that you form more of a personal connection with one, too. And then there’s the potential for it to carry an engraved message, hidden from view (which as we’ll see, can also get you into trouble). Give someone a watch and you’ll be following in the footsteps of some illustrious individuals: there is a long and famous history of watches being given by men and women in love.

Perhaps the most enduring example is the Breguet Grande Complication pocket watch number 160, commissioned in 1783 by a secret admirer (rumoured to be Swedish soldier Count Hans Axel von Fersen) as a gift for Queen Marie Antoinette, but not finished until after her death. Today, after a turbulent history involving theft and eventual rediscovery, the watch resides in The Museum of Islamic Art in Israel and is estimated to be the most valuable timepiece on the planet.

Closer to home, watches have long been favoured by residents of Buckingham Palace, a passion that began with science geek King George III in the 1700s. In more recent times, Prince Charles is said to have given Diana, Princess of Wales several timepieces, including a small, round, gold Patek Philippe. Their 1981 marriage was also cemented with a watch, given to Diana by the Queen. The symbolic gesture was magnified by the fact that the Vacheron Constantin cocktail watch had originally been given to the then Princess Elizabeth by the Swiss Federal Council on the occasion of her own wedding in 1947. The stainless-steel Cartier Ballon Bleu that the Duchess of Cambridge is rarely photographed without is thought to have been a gift from Prince William, while the Duchess of Sussex has been seen wearing a Cartier Tank Française. The gold version of the watch captured in recent pictures is rumoured to have once belonged to Princess Diana and, if true, then it is possibly one of the most intimate and treasured gifts Prince Harry has given to his wife.

When it comes to Hollywood royalty, no diva’s reign was more celebrated than that of Dame Elizabeth Taylor. A lover of gems, the eight-times married star was charmed by various suitors who seduced her with bejewelled delights, each with its own story to tell. The owner of several Piaget cuffs and watches of unknown origin, she was also spotted wearing a dazzling Bulgari Serpenti secret watch on the set of Cleopatra in Rome in 1960. Speculation remains rife about whether she bought the piece herself or if it was a gift from her husband at the time, Mr Eddie Fisher, or her lover, Mr Richard Burton.

The Burton-Taylor saga and her jewels are the stuff of legend. However, another shorter-lived but equally fiery affair is immortalised in a gold Vacheron Constantin dress watch that Mr Marlon Brando was photographed wearing in the 1950s and 1960s. The watch, which sold at Antiquorum in 2009 for $18,000, was given to the actor by Ms Zsa Zsa Gabor, one of his many lovers, after he won the Academy Award for On The Waterfront. The caseback is engraved “To Marlon Love Zsa Zsa June 24, 1954”. The passionate nature of the relationship was revealed on Mr Johnny Carson’s The Tonight Show when both Mr Brando and Ms Gabor were guests. Slightly worse for wear after downing neat vodka before and during the show, Mr Brando leaned in to Mr Carson, saying, “Do you know what I want to do with that girl, Johnny? I want to fuck her!” The words were later bleeped out, but the world was left in no doubt as to Mr Brando’s feelings.

Among the many timepieces that have immortalised love affairs, perhaps the most controversial one is the yellow-gold Rolex Day-Date that was allegedly given to President John F Kennedy by Ms Marilyn Monroe after she famously sang to him on his 45th birthday at Madison Square Garden. The watch’s caseback is engraved “Jack, With love as always from Marilyn May 29th 1962”. The story goes that it was a gift from a long-time lover, but, as so often happens, the evidence does not back up the story of a tryst between the screen siren and the president. Although many that were close to Ms Monroe suggested that there had been a brief fling in March 1962 when the pair met at Mr Bing Crosby’s house, Ms Monroe’s biographer Mr Donald Spoto stated that the two were only in the same location a total of four times, exploding the myth of a full-blown affair.

Less than three months after the Madison Square Garden spectacle, Ms Monroe was found dead of a barbiturate overdose at her LA home, aged just 36. A gift to the conspiracy theorists, rumours immediately started circulating of a politically motivated murder and a Kennedy family cover-up. Ms Monroe was supposedly having an affair with JFK’s younger brother, Mr Robert Kennedy, as well as with the president, and her untimely death only increased speculation on the relationships between the first family and the actress. It seems that the provenance of the Day-Date is as questionable as the affair itself – according to research by Mr Jake Ehrlich of Rolexmagazine.com, the serial numbers suggest that the piece was made two years after JFK died.

As with acting, music and timekeeping are indelibly linked, and one of the most poignant artefacts to ever come up for public sale is the white-gold Omega with diamond-set bezel that once belonged to Mr Buddy Holly. A gift from Ms María Elena Holly, his wife of four months, the watch was on the wrist of the 22-year-old Mr Holly on 3 February 1959, the day of his fatal plane crash in Iowa, which also killed fellow musicians Messrs Ritchie Valens and JP “The Big Bopper” Richardson. The timepiece, which is engraved on the caseback with “Buddy Holly 12-1-58”, was only found after the snow melted, fully intact save for a missing crown and winding stem. It sold in 2006 for $155,350.

Today, the new musical kings of horological bling – rap and hip-hop artists – are also fond of showing their love in a timely fashion. Jay-Z’s famed diamond-encrusted Hublot Big Bang, worth $5m, is said to have been a 43rd birthday gift from his wife, Ms Beyoncé Knowles, while Cardi B’s fully iced Audemars Piguet Royal Oak is one of a matching pair of sparklers commissioned by her on-off husband Offset. However they are dressed up – you may wish to declare your love with ostentatious gestures or discreet messages, layered with sentimental meaning invisible to all but the two of you – some traditions are here to stay.