This would be right after I spotted the black bear off the balcony and went TEARING through the suite shouting Gram’s name so she could see it too.

The basic rule is that you use less with mass nouns and fewer with count nouns.
A count noun is just something you can count. I’m looking at my desk and I see books, pens, and M&M’s. I can count all those things, so they are count nouns and the right word to use is fewer. I should eat fewer M&M’s.
Mass nouns are just things that you can’t count individually. Again, on my desk I see tape and clutter. These things can’t be counted individually, so the right word to use is less. If I had less clutter, my desk would be cleaner. Another clue is that you don’t make mass nouns plural: I would never say I have clutters on my desk or that I need more tapes to hold my book covers together.

Basically. You can go read the whole article if you want. So since I was talking about boobs at a Bette Midler concert, which I could have, theoretically, counted, “fewer” would be the correct usage when comparing it to a Steve Martin and the Steep Canyon Rangers concert. I’m glad we got that cleared up.

“Were” used this way is called the subjunctive mood.
This mood is used to express a wish or possible situation that is currently not true. It’s usually used with words like “if” and “wish”.
Other examples:
“I wish I were a sea cucumber.”
“If I were you, I would eat less bacon.”

That, I will never forget.