User blog comment:B214/Question and Answers 6/@comment-32559006-20180223160008/@comment-33359929-20180223173625

I highly doubt it. Issei is engaged to at least half of Rias' peerage, and judging by how they all reacted to his death, I don't think they'd be able to take it if Issei wanted to break up with all of them.

It's mentioned that Asia in particular wanted to kill herself after Issei 'died'.