As long as Jedi is healthy and free of parasites and disease, I see no reason to restrict them from playing together, inside or out. The only thing you want to watch for is overly rough playing, running and turning too fast. Just use common sense. If they get too rambunctious, give them a time out or distract them for a few minutes. This does require supervision, of course.
Your puppy can play outside, but don't expose him to other dogs or their droppings until he's had his puppy shots. Talk to your vet.
It's best to get a pup used to his environment early on. Socializing and playing are important to his development. Start training him right away, too. An 8 to 10 week old pup is not too young to learn basic commands. Just make sure your training is lots of fun for him. Now is a good time to start teaching recalls. Expect a short relapse when he's a little older, but don't give up and be consistent.