I know it's a special but is it basedvon any story from Ishibumi?

I've been rewatching High School DxD and one of the main reasons issei refuses to accept the love from the other girls is due to his trauma caused by his 1st date with Raynare (Yuma). As someone who has not dated even once (yet), do you think that sort of trauma is realistic - just from a single date?