Overly complicated regular expressions are hard to read and to maintain and can easily cause hard-to-find bugs. If a regex is too complicated, you should consider replacing it or parts of it with regular code or splitting it apart into multiple patterns at least.
The complexity of a regular expression is determined as follows:
Each of the following operators increases the complexity by an amount equal to the current nesting level and also increases the current nesting level by one for its arguments:
p = re.compile(r"^(?:(?:31(\/|-|\.)(?:0?[13578]|1[02]))\1|(?:(?:29|30)(\/|-|\.)(?:0?[13-9]|1[0-2])\2))(?:(?:1[6-9]|[2-9]\d)?\d{2})$|^(?:29(\/|-|\.)0?2\3(?:(?:(?:1[6-9]|[2-9]\d)?(?:0[48]|[2468][048]|[13579][26])|(?:(?:16|[2468][048]|[3579][26])00))))$|^(?:0?[1-9]|1\d|2[0-8])(\/|-|\.)(?:(?:0?[1-9])|(?:1[0-2]))\4(?:(?:1[6-9]|[2-9]\d)?\d{2})$")