однако, когда он говорил и улыбался

однако, когда он говорил и улыбался, лицо его сразу же становилось очень приятным

Результаты (английский) 1:

However, when he talked and smiled, his face immediately became very enjoyable

Результаты (английский) 2:

however, when he said, smiling, his face immediately became very enjoyable

Результаты (английский) 3:

however, when he talked and smiled, his face immediately became very pleasant