Instead, Jon proposed, she accepted, they exchanged vows in a secret marriage ceremony in Malibu, California, on Jan. 20, and they even confirmed they'd said "I do" to the press.
But less than two weeks later, the former "Baywatch" star told The Hollywood Reporter that she and Jon, 74, had already to "take time apart to re-evaluate what [they] want" from life. So what happened?
According to Page Six's insider, Pamela was "vulnerable" when she said "yes" to Jon's proposal, having just returned to the U.S. after a monthlong cleanse in India where "she was doing constant meditation and yoga," which left her feeling "very open." The source also described Jon's 30-odd year romantic pursuit of the actress, telling the outlet she agreed to meet with him for lunch while they'd been texting while she was away.
"The day she returned, Jon invited family and friends [over for lunch] and proposed to her," the source continued. "He had a friend 'officiate.' Essentially, it was a sweet ceremony, but ultimately, [no license] was filed."
Meanwhile, Pamela was already starting to feel "homesick for her ranch in Canada" and soon found Jon, whom the source called "controlling," was reportedly not interested in allowing her to remain financially independent.
According to Us Weekly, though, it was Jon's idea to break up, which he reportedly did with a text in which he told Pamela, "this whole marriage thing has scared me" and "at 74, I need a simple quiet life, not an international love affair," among other things.
Pamela had spent half the time they were married at her home in Canada, according to Us.
Jon allegedly went on to say the best move for them would be for them to both go their "own separate ways" and said he hopes she could forgive him.
In a statement to People on Friday, Pamela sounded comfortable with their decision.
"Jon and I have been friends for a very long time. He has been nothing but nice to me and, for that, I love him," she said in the statement. "Jon opened up his heart and home to me, has helped me through sad times, and I only have kind words to say about him. We remain friends."
Pamela, 52, was previously married to Mötley Crüe drummer Tommy Lee, Kid Rock (2006-2007) and poker player Rick Saloman.