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I am SO embarrassed. I apparently never made it clear in my Courtship and Marriage Guide that you meet Skye for the first time by experiencing his First Heart Event.
I have received a possible deluge of emails from players today who have been wandering the paths of the Valley searching for Skye in vain... As a matter of fact, I believe I did that myself in my first game, so I should have been aware of the danger of not stating very clearly that his First Heart Event is your first meeting with him.
Skye really does break all the rules. Ordinarily, you must meet an individual before you can experience any event with him/her. Skye of course, is an exception to THIS rule as well as many others.
Walk up the staircase towards the Villa between 10.00 p.m. and 11.50 p.m. on any sunny night and you will meet Skye for the first time in his First Heart Event. AFTER that, you will find him at the entrance to the Valley at 10.20 on sunny nights. He then crosses the bridge and walks up to the Goddess Spring where he stands until dawn.
By the way, you never will see him the night after one of his Heart Events, but the following night, he will resume his regular path...
There is another anomaly about Skye that may be worth mentioning. Between his First and Second Heart Events, I did find him once on the path between Turtle Pond and the Blue Bar. Once he 'hit' the Blue Bar in his Second Heart Event, though, I never saw him anywhere but on the path that leads from the Valley entrance across the bridge and then north to the Goddess Spring.