Well, we actually had some success today, i was so proud of him!
I carried him outside, and let him walk around with the leash dangling. Hes a very timid dog to begin with, so he was just sniffing about, and slowly picked up the leash. He will walk approx 50 feet from where i place him down, then go back, lol. And found his way to my front door to go back inside!
Im sure there will be a day he'll be begging to go out, haha. Macy does. We never had this problem with her.
And he is 6 months by the way!