Dear Prudence,
I recently found out my boyfriend still keeps nudes from his exes (he’s only admitted to one, but there could be more) and that he masturbates to them from time to time. We live in different states, and I plan to move to his city soon. He is a decent guy, and we love each other. He didn’t see anything wrong with it, but to me it feels closer to cheating than to watching porn, mostly because of the personal romantic history. I was upset when he told me about it, but I also appreciate that he told me himself and wasn’t trying to hide it from me. I want us to understand each other’s perspective. But it felt like a betrayal, especially since I haven’t deprived him of nudes of myself. He told me he is sorry he hurt me and says he will delete them. The problem is that I don’t believe him. From previous experience, I know he hates “erasing history,” as he calls it. For example, he had a hard time deleting my own pictures stored in his hard drive. I had asked him to get rid of them multiple times because I was not comfortable with my nudes being stored anywhere. I’m the type who would prefer them deleted once we’ve finished sexting and to send new ones next time. I understand I may never find out the whole story, but I can’t help but hope that I will be able to tell if he’s telling the truth once I confront him in his face. Should I confront him? Am I wrong to equate keeping those pictures to him not giving my feelings and our relationship the highest regard?
—Forever in the Cloud