This wasn't difficult for me, but may have been for a friend. At high school, a good friend and I used to chat during breaks. A mutual friend had t get circumcised, and I asked "I wonder how cut gutys can get hard, wouldn't the skin get too tight ?". He said "I wouldn't know, I'm not cut either".
Fast forward a couple pf years , and we are next to each other at the locker room. We undress and it turns out he is cut. He never said anythig about it. My guess is that he must have realised that he too needed to get cut because his skin couldn't go back, but when he first undressed in front of me, he was probably affraid I would notice he was now cut since he had told me earlier he was uncut. Didn't say a thing.
Another one: much younger, we wre 3 friends together. One was teling us that at class some guy went around asking guys if they were cut/uncut. So I asked him what his answer was. He refused to answer.
Fast forward many years, and this guy is at the same pre university school. He drops pants at locker room to reveal an exposed glans. So I finally had my answer... or so I thought.
A few weeks later, we are both taking showers, I wentr in with foreskin over head and he went in with head exposed. When we exited the cubicles to dry off, to my great surprise, and in fronr of me,he pulled a foreskin over all of his head. Ironically I had my head all exposed at that point. It was the only time I saw him with covered head, all other times afterwards, he had his head exposed. My guess is that he finally answered the question he didn't want to answer as a kid, but just when we were alone in the shower room.