So I've done incredibly silly things with a friend of mine over the past couple of years and there are a ton of pictures and videos where I look bad.
I want to get rid of all those compromising photos and videos which would immediately destroy me in the eyes of anyone.
I can sit down with him and ask him to go through everything on his phone together and delete whatever I deem horrendous. I know nothing about iCloud and backups and whatnot. I want a guarantee that everything will be deleted (after also deleting the contents of the "recently deleted" album) – from all backups and clouds and devices.
Is there any way for me to be certain of that?
He owns many iPhones and uses at least 2 at any time. He also has Macs and an Apple Watch. He is also paying for iCloud. I also own an iPhone but he is the true Apple power user and he can play me any way he wants to. He has some of my passwords too.
Best Answer
The answer to your question in the title is one thing, but then there's the question within your post:
For all practical purposes that question can really only be answered as a no. To be clear, you can never be 100% certain.
However, the closest you can get (without him losing all his other data*) is to arrange a get together with him at his home (without any indication as to why) and then be there with him as he:
On his Mac
On his iPhones/iPads
Back on his Mac
IMPORTANT
* That is, it is not realistic to expect him to take more extreme measures to give you this certainty as it would involve him losing all his data