I think it is completely okay for OP to ask considering these are intimate tapes/videos not love letters in a box somewhere, or photos from the beach tucked away on a computer file or something. These are INTIMATE photos/videos whatever, and even if he doesn't look at them that little cringe of thinking they still exist in his possession is enough to kind of drive someone wild IMO. I personally think OP, you should wait until you do talk with him about something somewhat relevant, like sex tapes or something if you two ever talk about creating one, or if porn comes up in general, or even the ex for whatever reason. I would play it off more so like "hey do you still have those videos of you two? haha" kind of light hearted... Doesn't translate well over the internet i know. But yeah I would mention it because I can almost guarentee he'll laugh and be like ha what no way especially if it ended poorly, or he'll be like oh yeah man i forgot to delete those. Even if he does say yes, you can just try and be casual and just say hey you know what would you mind deleting them, even if you don't look at them they make me uncomfortable etc etc. Either way, you'll get a peace of mind in knowing whether or not he has them, and as long as you guys communicate well (which it seems like you do) I'm sure everything will be okay. Best of luck! /u/hersextapes11