The short answer to this question is no. Bob does not know that Bingo and Rolly talk.
However, it is possible that they have spoken in the past and that Bob was not aware of it. It is also possible that they have not spoken recently, but are currently speaking.
The long answer to this question is more complicated. It is possible that Bob knows that Bingo and Rolly talk because they have interacted recently.
It is also possible that Bob knows that Bingo and Rolly talk because they have interacted in the past. It is also possible that Bob does not know that Bingo and Rolly talk, but could be aware of their relationship based on other information.
Ultimately, it is difficult to say for certain whether or not Bob knows that Bingo and Rolly talk. However, based on the information available, it appears as though he could be aware of their relationship in one way or another.