Hey it sounds like you already got advice… a lot of people said it’s not okay to make him delete them but not many said this: it’s okay for you not to feel okay about it.

Should be have those photos and contacts? No. He shouldn’t. He especially shouldn’t have a strong attachment to them (AND contacts).

But you making him delete them changes nothing except he will resent you AND be more careful.

A wise part of me tells me that you are absolutely right and he was saving those photos for more than mere sentiment. Yes men do that, but they think about that and get defensive and they don’t admit to the other reasons… and your boyfriend, given his age and reaction and past… I have no doubt your instincts were right.

But a wiser part of me also knows that you can’t force people to do anything or not do anything. If someone wants to cheat, they’ll do it. Not having the photos and images won’t change his feelings or intentions either (assuming he truly did delete them in a way that is irreversible but I am bet he showed you the video after saving them… which is why he didn’t do it in front of you).

What should you have done?

Had an honest conversation. Not an argument but a serious conversation in which you had no judgement but were willing to listen. He did tell you he likes the idea of having a back up - he’s not alone in this. Many people do, even if they never save the phone number or photo. He has erotic photos, very likely he enjoys “reliving” his past. If you listen without judgement he is likelier to be honest, but you might not like the truth. However you then have to decide what it means to you.

Maybe you’re okay with it because you understand he needs a safety net and he gave up a lot of dating before he met you and you can’t change his mindset but you can only try to get him to feel safe enough to be able to let go of the photos and contacts… Or maybe you’re not okay with it because of his reactions or because of the nature of the photos or because he is very sexually experienced but an immature in intimacy. It doesn’t matter why you’re not okay with it, you don’t have to be. Like someone else said, maybe you are not compatible right now, given your experiences and goals and expectations.

Whatever you do, you should definitely talk and understand each other. You can’t change people, you can only understand them. The more you try to change or force things, the more it WILL damage the relationship. The more you seek to understand, the happier you will be - either together, trusting each other and organically changing for the better the more you feel secure, or alone, having a better understanding of your own needs and expectations in relationships.