Prep all ingredients per the instructions above.
Preheat oven to 350°F (176°C). Spray a loaf pan with cooking spray and line with parchment paper.
Mix together the butter and the sugar until combined. Add in the eggs and whisk until completely combined and the mixture is smooth. Pour in the milk and vanilla. Whisk into the batter until smooth.
Add in the mashed bananas and mix into the batter. Add in the flour, baking soda, and salt. (Alternatively, you can whisk together all of the dry ingredients together in a separate bowl and then add into the wet ingredients.) Using a rubber spatula, gently stir, or fold into the batter, until the ingredients are just barely combined and no more flour is visible.
Pour the batter into your prepared loaf pan and spread the batter to make it smooth. Bake for about 1 hour (or until a toothpick or tester inserted comes out dry). Let cool while you make your cream cheese frosting and coffee.
Using a stand mixer or electric hand mixer, mix the butter and cream cheese until smooth. Add in the powdered sugar and vanilla and mix again until smooth. Spread on cooled banana bread.
Brew and prepare the coffee to your liking.
Serve banana bread with coffee.