Both with an O here.

Are the two obviously differentiated like that?

In most of the American English accents I’m familiar with, they’re pronounced “WI men” and “WŌ man.”

If I try to sound out using an I in both, the only way they sound different to me is if I move the accent to the final syllable, to mane it stand out. Something like “wi MEN” vs “wi MAN.”

If so, I’d love to hear where you’re from.

I think the meme is referring to the first vowel.

Same, i think its a regional thing.