And now UK newpapers are reporting that the moment has arrived – just eight months after the royal sweethearts called it a day.
The pair are said to have been swapping intimate messages on social networking site Facebook and have also met in secret to discuss their future.
Harry is apparently hoping to win 23-year-old Chelsy back when he moves to London next month to start the advanced stage of his pilot training with the Army Air Corps.
With the pretty blonde also in the British capital to begin work with City legal firm Allen & Overy, it'll be the first time they've ever lived in the same area for a substantial period of time.
However, they are apparently both aware that the circumstances which forced them apart haven't changed.
Chelsy is thought to have been upset at the amount of time Harry's army career kept them apart, and unhappy about the public scrutiny that comes with being a royal girlfriend.
The Zimbabwe-born beauty has stepped out with other male companions in recent months, namely property developer Dan Philipson and banker Dominic Rose, but the relationships were not serious.
Meanwhile, 24-year-old Harry was also linked for a few weeks to vivacious TV presenter Caroline Flack.
Tellingly, just a few weeks ago, Chelsy seemed to suggest their romance wasn't a closed book.
"It's not easy to predict anything, So I just think it's better to get on with our careers and see where time takes us," she said, as reported by the Daily Mail.
"We've stayed good friends… but it's hard to block out someone who has been there every single day for a long time."