Cut bananas into slices and freeze until solid, overnight, or 2-3 hours.
In a food processor or blender add frozen bananas and blend until pieces are small.
Add peanut butter, milk, and optional sweetened condensed milk. Blend until smooth and creamy.
Split mixture across 10 popsicle molds and freeze overnight.
For the chocolate dip heat up chocolate chips and coconut oil in a saucepan on low heat stirring constantly. DO NOT WALK AWAY, you don't want the chips to overheat and seize. Once melted remove off the heat and pour into a tall mason jar or container that is deep enough to dip the popsicles. If making the dip right before dipping let it cool to room temp.
Remove popsicles as per mold instructions, don't rush this.
One by one dip the popsicles in the chocolate dip. Shake off any excess back in the mason jar or container. From here you can place it on parchment paper in the freezer or hold for a minute until the dip solidifies and then place it in the freezer.