we have been working very hard on socializing and getting our pup comfortable with people.
He has shown some small progress but not a whole lot

until today!
We went for our walk and since it was so pretty out there were people everywhere, he greeted a woman with a tail wag and sniffed her hand like it was no big deal. Which is a huge deal.

Then there was a Big man, in the sens of tall and buff out running, we were stopped at the corner and he calmy watched this guy run towards us and then past with no reaction but mild interest.
two weeks ago he would have been hiding behind my legs and barking.
Then my nephew came by this afternoon, He did bark some at him but it was more of a simple vocalizing as he didnt run off or hide or raise hackles or any of that. And he is a noisy pup,
he kept going and sitting next to him and looking at him and barking. After about 10 little tiny treats from my nephew pup calmed down and stopped barking at him and actually initiated play and then iniated affection and allowed my nephew to pet him on the cheek and even the top of the head..
He would accept the pet and then back off a little and look at my nephew for a minute and then go right back for more.

by the end of the visit (about 2 hours) he was mouthing his hand and sitting by him on the couch and bringing him a toy to play!!!

that's great jennifer! how rewarding all your work is paying off!

I was just wondering why do you think he's been so uncomfortable with strangers? Did he have a bad experience once or is this something in his temperament that you're trying to work out?

That's great Jennifer, my puppy is similar to yours and is coming along nicely as well. Hard work does pay off, it seems.