I don't feel inclined to do anything to cover up for his weird behavior. If I do anything to accept blame for the awkward interaction I feel like I'd just be inviting more.
Well that's true. Why play games, I guess...
But you're an airline pilot, so you're much cooler than normal "old economy" guys. 
Huh ? Oh... you're quoting other people in here too...
Something about the whole interaction just felt very strange and off-putting.
Maybe he's trying a new tactic to get you on his side. Since his "way" is so alien to you, you didn't pick up on the motivation and it seemed weird ?
I don't think he was trying to hit on me or anything like that. I just don't get where it was coming from. Like, the dude is talking to me as if I'm a school age child, so that's somewhat insulting already. Is he just making light of me being much younger than most of the others in the office? Is there something more sinister? Is he picturing me in a little plaid skirt? Is he imagining telling me to stay after school for a "special detention"? I really don't know. I'm just not sure what to make of this.
The last few suggestions would be a 'hit on' thing. It sounds like he desperately wants to be liked. And you do not like him.
I do know that if he does say anything about plaid skirts or detentions or corporal punishment, I will kung-pow his head right off his body. It will be the kind of violence you would normally only see in Japanese animation. Like, One Punch Man, Fist Of The North Star type violent. I will go Super-Saiyan on him.
Or just quote some Anime to him and look at the confused look on his face.
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