Complex sentence: When Bobby was asked how it felt to be back around the group since their separation, he jokingly made remarks about hoping to get back with the group, and the men made jokes that it could possibly happen, while showing their doubts that it would happen.
Split into simpler sentences: When Bobby was asked how it felt to be back around the group since their separation, he jokingly made remarks about hoping to get back with the group. The men made jokes that it could possibly happen, while showing their doubts that it would happen.