User blog comment:B214/High School DxD New 12 discussion/@comment-1392308-20130924035226/@comment-1359322-20130924042057

Most of Issei's crying isn't serious, the one where he was seriously crying was probably during Asia's death, when he lost to Riser which are tears of frustration and when Kiba was surrounded by his friends' spirit. The others were only used for comedic purposes or for his perverted thoughts purposes like this one, he cried over the thoughts of his favourite breasts being halved.