Pit and coarsely chop the 4 Medjool dates, then add them to a blender or food processor with 1/4 cup of the milk. Blend until you create a smooth, creamy paste—this will act as a natural sweetener and thickener for your overnight oats. The dates will dissolve into the milk, creating creaminess without needing yogurt. If you don't have a blender, you can finely mince the dates and whisk them into the milk until mostly broken down.
In two mason jars (or similar containers), divide the 1 cup rolled oats and 2 tbsp chia seeds evenly between them. Add 1/2 tsp ground cinnamon and 1/8 tsp kosher salt to each jar. Pour the date paste from Step 1 into the jars, then add the remaining 1.75 cups milk and 2 tbsp honey (if using). I like to add the honey directly to the wet ingredients as it incorporates more smoothly this way rather than trying to mix it in after assembly.
Seal both jars tightly and shake vigorously for 30-45 seconds, making sure all the oats are submerged and the mixture is well combined. This ensures the chia seeds and oats are evenly distributed and start absorbing the liquid immediately. Place the jars in the refrigerator and let them sit overnight (or for at least 4 hours, though 8+ hours is ideal). The overnight rest allows the oats and chia seeds to fully hydrate and create that signature creamy texture.
In the morning, remove the jars from the refrigerator and give them a good stir—the mixture may have thickened considerably or separated slightly, and stirring will recombine everything into a creamy consistency. If the oats seem too thick, add a splash more milk (1-2 tablespoons at a time) until you reach your preferred texture. I find that even overnight oats can vary in thickness depending on how much the oats absorb, so tasting and adjusting is key. Top with sliced bananas, chopped nuts, or an extra drizzle of honey if desired, then serve directly from the jar or transfer to a bowl.