Shoulf I talk to him about it?

My boyfriend and I both have a very hard time trusting. We have been together 3 months, but we both have had pretty horrible experiences with past relationships where he have been cheated on, so we understand that is really hard to really trust someone. Since the beginning we gave each other our phone passwords and he told me he really doesn’t mind if I go through his phone and I told him the same. I have only checked his phone like 3 times, but yesterday I found a conversation with this girl. He once told me that she always liked him but nothing happened between them, he just sees her as a friend and they get together to smoke sometimes. I told him it was fine. I already met her like 2 times, and he introduced me as his girlfriend. About a week ago I got together with my friends one day, and we were texting each other and he told me he was going for a walk, but yesterday I found out he went to her apartment to smoke with her. I know she is her friend but if he purposely doesn’t tell me that they are meeting alone it makes me doubt. Should I ask him about it? He would know that I went through his phone but since the beginning he said he doesn’t mind.
Shoulf I talk to him about it?
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