So this took me a lot of digging to figure out.
DialogFragment's show method only adds fragments hence if you want to replace them you have to manually remove the previous dialog fragment.
One thing to keep in mind, it is important to use the same fragmentManager used to open the initial DialogFragment. For example if you opened the first DialogFragment via an Activity (supportFragmentManager) and now using the DialogFragment's fragment manager (childFragmentManager) since they do not have the same stack you wont be able to access the original DialogFragment and remove it.