First, roast the garlic. To do this, take one whole head of garlic and cut that top off to expose the garlic cloves inside. Drizzle with about 1 teaspoon of olive oil and wrap tightly in foil. Add to a 400 degree f oven for 50 minutes.

Dice the potatoes into 1 inch cubes and place potatoes in a large pot. Fill with cold water about an 1inch or so above the potatoes. Add to the stove top and bring to a boil and boil for 15-20 minutes or until the potatoes are fork tender. 

Drain the potatoes and add to a large bowl. To mash the potatoes, you can use an electric hand mixer, hand masher, potato ricer, or a stand mixer. I personally like to use my stand mixer because it is so easy to use! 

Add the butter and milk to a medium saucepan and heat on low heat until the butter is melted. Add the melted butter and milk to the potatoes. Then, take the head of garlic and squeeze out the garlic cloves. You can first add them to a small bowl and mash, or just add them directly in with the potatoes if you want bigger chunks. 

Season with salt and pepper and then mix all the ingredients together until the potatoes are mashed and creamy. Be careful not to over mix though. This will create a gummy or gluey texture. 

Add to a serving bowl and serve. Top with gravy if desired and enjoy!