So there was a sense of déjà vu on Saturday when the 24-year-old was pictured next to the handsome royal at a fixture between England and Australia – the strongest suggestion to date that their romance is back on.
Braving the chill at Twickenham, Harry and Chelsy initially watched the action with a friend sat in-between them, but the Zimbabwean blonde moved to be alongside the prince for the second half.
While there has been no confirmation they have reunited romantically, the couple's obvious delight at being in each other's company – they were snapped leaning in and laughing together - has further fuelled the belief their relationship is back on.
And no doubt fun-loving Chelsy's presence lessened the blow of England's defeat against the Aussies for keen sports fan Harry.
Last month royal watchers were delighted by pictures of Prince Charles' second son and his former flame of five years leaving a London restaurant together.
She was also present at the 25th birthday celebrations for Harry in September.
"They are officially back together but it was a long process," said a friend of Chelsy, who was said to be keen to form her own profile before re-embarking on a relationship under constant media attention.