We're really understating just how bad mass-communication was in these days the story is set in an age where communication over long distances was, at best, unreliable. To be fair to Westley, it's not as if he could have just sent an email to Buttercup or texted her immediately with the information or even sent her a telegram.This way, as stated above, he could go about his original plan and once he'd earned his fortune come back and rescue her from her engagement (because, naturally, that would be no problem since they had the power of true love). If Westley told Buttercup that he was still alive, she'd have refused to marry the Prince and been killed for it.being an oddly practical fellow, he just thought he'd found employment in an unexpected place and was going about the original plan. Remember he was going across the sea to seek work anyway, and thus likely planned on being gone for several years in any event. So most likely he just got about the business of surviving and learning to be a Dread Pirate and figured once he'd found a suitable replacement he'd head back to Buttercup (who would be totally unsurprised to see him alive, to his thinking) and they'd live the rest of their lives comfortably on his retirement fund. Simplest explanation: being the massive, utter, and hopeless romantic that he is, Westley simply assumed that Buttercup would think "Oh, he's alive, and he'll be making his way back to me any time." He pretty much says as much after he asks her why she didn't wait, he just takes it as a given that she'd assume even death wouldn't stop him from coming back to her.It may not have been easy to do that and still maintain his cover.It's irritating he didn't make some attempt to reassure her. Couldn't he have done that and let her know he was alive? If he'd sent a message saying "I'm still alive, but am working to provide your future" (his original plan), she would have happily waited it out and refused to marry the Prince.Also, Westley likely wanted to build up a nest egg, so that he could give Buttercup a better life than living on a farm when he returned.That would drum up questions about how Westley escaped the Dread Pirate Roberts - or if the Dread Pirate Roberts spared him, which is impossible because, of course, the Dread Pirate Roberts leaves no survivors.Still, he COULD have sent a message any time in those five years, considering that he wasn't actually a prisoner - he was Roberts' valet. It's just that after three years the previous Roberts stops saying that he'll most likely kill Westley in the morning. He doesn't become the Dread Pirate Roberts after three years.And then he has the gall to be angry at her for being 'unfaithful"! Instead he just hangs around playing with swords and puts his 'true love' through TWO YEARS of unnecessary grief and pain. That means that at any time he could have headed back to the farm (or even sent a message) and TOLD Buttercup that he was still alive. Westley was gone five years, but while in the Fire Swamp he explains that he was only held prisoner for three years before becoming 'Dread Pirate Roberts'.Why didn't Westley contact Buttercup sooner?.
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