Complex sentence: Grif becomes annoyed when Simmons doesn't scold Caboose for trying to blowing their cover, and then comments on Simmon's inability to communicate with his all-female squad, which makes Simmons remember his time at junior high.
Split into simpler sentences: Grif becomes annoyed when Simmons doesn't scold Caboose for trying to blowing their cover. Grif then comments on Simmon's inability to communicate with his all-female squad, which makes Simmons remember his time at junior high.