Despite his apparent big feelings for her, Isabella Calthorpe reportedly turned down Prince William a number of times during that 2004 summer trip. Author Kate Nicholl has examined the dynamic between the two and wrote that William approached Calthorpe "a number of times" about being together, but that Calthorpe rebuffed his advances each time. As it turns out, Calthorpe had her sights set on something bigger than a crown: her own successful career.

As a source told Nicholl for The Daily Mail, "He propositioned her several times that summer and although Isabella was single, she knocked William back and said it would be too damaging for her and her career. She is a name in her own right and on her way to becoming hugely successful. In her view, being affiliated with William in a girlfriend capacity would be damaging for her."

Calthorpe later told The Daily Mail that while she appreciated the attention she received for being an "it girl" at the time, fully taking on the role never would have been enough for her. Calthorpe explained, "The thing about all that It-girl stuff is that it would never satisfy me. Looking back I think I could have slipped into that world when I was 17 or 18 and there was this press attention and pressure, but I felt strongly when I was quite young that it is dangerous to exploit yourself in that way."