Might be a patience thing too? Most cookies will take some time to really absorb a meaningful amount of milk. Like Oreos take a good 10 seconds submerged. You can see bubbles as milk replaces air in the cookie.
There are some rare cookies that will absorb the milk way faster, like Keebler Vienna Fingers will be soaked in like a couple of quick dunks.
Shitty milk tastes shitty. I have no understanding why schepps continues to exist. It's like they have stripped everything that makes milk milk, and now just sell white water. I'm not a huge fan of Borden either, but that's just a taste prefer. At least Borden is still milk.
People who drink 2% or 1% milk? WTF are you even doing with your life? Whole milk is only 3 or 3.5%, so how much fucking milk are you drinking that 1% less fat is going to save your life? Do you dip your cookies in that shit? Why do you hate yourself? Did you know that fat slows your digestion? By removing fat from your milk and cookies or milk and cereal you're actually speeding up how fast the sugar hits your blood stream and increasing how concentrated it is going to be.
So, maybe you hate milk and cookies because you have been drinking shitty milk.
My family used to drink milk for dinner. We probably went through ten liters of milk in a week. The top third of the fridge was always reserved for milk.
When i moved out i continued doing this for a while or eating cornflakes in milk, but eventually stopped because my adult body is not that fond of digesting milk. I eat crazy amounts of cheese though, but the well cured one that are low on lactose.
I think it's used in a lot of ways that isn't "drinking a glass of milk". I suspect most milk is poured over cereal. It's also used a lot in cooking, but insisting on raw milk to bake with seems especially weird.