The reason why the error message mentioned OpenSSL 1.1.1+ and LibreSSL 2.8.3 is that urllib3 v2.0 ( version you’ve installed) requires OpenSSL 1.1.1+ to work properly, as it relies on some new features of OpenSSL 1.1.1.
The issue is that the version of the ‘ssl’ module that is currently installed in your environment is compiled with LibreSSL 2.8.3, which is not compatible with urllib3 v2.0.
To use urllib3 v2.0, you need an ‘ssl’ module compiled with OpenSSL 1.1.1 or later, by trying :
brew install openssl@1.1
Or you could use an older version of urllib3 that is compatibl suc. For example urllib3 v1.26.6, which does not have a strict OpenSSL version requirement.
You can force the version installing with this command:
pip install urllib3==1.26.6