I have noticed a similar thing:
Someone asks if the frequency is in use once: I say yes (this is on CW).
They ask again: I again say yes.
Then they call CQ.
It's almost like it's a custom to ask if the frequency is in use, but the answer doesn't matter. You just have to go through the ritual of asking.
And no, I don't think for a second that he couldn't hear me.
Channelized 60 meters presents specialized problems where most DX is worked on Channel 5 (5305.5). I'll ask if the frequency is in use before calling CQ DX but often a stateside station will interpret my check as a general CQ and want to chat.
Couple of nights ago a stateside lid calls at least 20 CQs nonstop on the calling frequency at sunset. He finally shuts up and I jump in with a quick CQ DX looking for Europe. He then replies that it was his frequency and that I hadn't asked if it was in use (I didn't want to talk with him).
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Asking whether a frequency is in use has become a required ritual even when useless. My business desk is near my radio which is often on. I'll know damn well a clear frequency isn't in use. But when I've plunged in with a CQ, I've had stations come out of nowhere complaining I hadn't asked public permission to CQ.
Then you have the stupid formalities that have developed. I don't recall any of this nonsense 40 years ago. W6AM would just wait for his big bottles to heat, pick a rhombic and leter-rip! But now we have...
"Is the frequency in use?"
"Is the frequency in use?" {sometimes ask even a third time!}
"Nothing heard" [pause once more]
What's the point of announcing "nothing heard" before CQing?
