Complex sentence: They both annoy Red greatly, particularly Bob, and Red makes little to no effort to hide his annoyance, but no matter how many times he insults Bob, Bob just smiles and laughs it off because he thinks Red is just kidding.
Split into simpler sentences: They both annoy Red greatly, particularly Bob, and Red makes little to no effort to hide his annoyance. No matter how many times he insults Bob, Bob just smiles and laughs it off because he thinks Red is just kidding.