I was talking about Coriolis effect with someone and he asked me about
planes against or with the earth's spin of around 1000mph at the equator. He
asked why this didn't benefit east to west plane travel timewise and hurt
west to east. I couldn't give him a straight answer, and felt like an idiot
when I said "it just doesn't".

What IS the straight answer? The dropping something in a moving vehicle
analogy doesn't work, does it? A plane has a method of acceleration, whereas
a passively dropped object doesn't.

Sometimes really simple questions can give you the worst time.