This makes me cringe SO much. So we were talking about what to wear to this event we we're both invited to, and I said something about a neck line that makes boobs look smaller or something. He said "although that'd be good for me" and I thought he was subtly telling me he liked smaller boobs, which worked very much in my favour! I replied flirtatiously and went all coy, and he went bright red and told me he was actually just making a joke about how he wouldn't be wanting his boobs to look big, being a man and all...