Most Helpful Guy
I broke up with someone I really loved and cared for about two months ago. I am dating someone new and she is awesome. I recently started deleting the photos of my ex. It is normal. Over time he will delete them. If you point it out that he still has her photo, it will be a problem. Trust me. It takes time for guys to get over an ex. It takes guys a lot longer than women. But this is normal. If you flip out, he will never trust you. If you just let it be. He will move on. I held on to the photos because they were great memories. Now that I am building new memories with my new girl, I have been deleting the old photos of my ex. Just have some compassion. Don't judge. Relax. Be a "better option."
Most Helpful Girl
Chat conversations I dont think they'd care one way or the other. Images are a different matter, if you have ever sent a guy or an ex a nude selfie then there's 98% chance he still has it somewhere on a hardrive somewhere with other girls who sent them. At my school there was a bit of a thing where guys would share nude selfies of girl, it was at the stage where when I was going through an ex boyfriend's computer there was pics of nearly every girl in school. Thats why I never send nude selfies anymore not that it matters because once the pic is on the web there's no taking it back.