Many breeds have a normal propensity to look long and hard at anything new. It is certainly an issue with a Chessie.  CBRs are visual, thoughtful, and naturally protective, which also look like a very cautious and suspicious approach. 

When approaching any dog for the first time, always go slow, especially if you have your dog with you.

Chesapeake Bay Retrievers, like many breeds,  will most often see a direct stare as a challenge.  When meeting new dogs or people watch your dog and be aware of any direct staring.