Wheels of Justice (named for proprietor Justice Baxter) on Mountain Blvd. in Montclair is staffed by very friendly folks who definitely don't make you feel silly for asking low-tech questions. They're trying to form a cycling community around the store with group rides, semi-annual "Grand Re-Openings" (with beer, pizza and karaoke) and an amazing trade-in policy for kids' bikes. They also offer free lifetime repairs and maintenance for bikes bought in the shop.
The store can be a bit of a mess, and the selection could be better, but as someone who spends a lot of time on my bike and in bike shops, this is where I choose to spend my money.