Ironically, their paths crossed again shortly after, in 1958, when they were cast together in Houseboat, a romantic comedy written in part by Grant himself. He had originally tailored the film as a vehicle for Loren, hoping to work with her again — and perhaps rekindle their relationship. But by then, the situation had changed. Loren had secretly married Carlo Ponti by proxy in Mexico, a legal workaround since Ponti was still unable to divorce under Italian law. The chemistry between her and Grant remained undeniable on screen, but behind the scenes, there was a quiet sadness — a sense of longing for what might have been.
Grant later admitted that filming Houseboat was one of the most emotionally difficult experiences of his life. “She was there,” he said, “but she wasn’t mine anymore.” Their romance never turned scandalous. It remained dignified — a private heartbreak known only to those closest to them until years later. Loren, for her part, kept every letter Grant ever wrote to her, stored carefully in a box she never discarded.
