It's incredibly easy to get a little bit into either. Ruby however hits a HUGE hockeystick of difficulty when you start to use the web tools (the primary use case for ruby).

Python however seems to have tons of non-expertise intensive uses that are not primarily used by professional programs. Scipy et all, etc. The "mouthfeel" of the communities is considerably newbie friendlier on the python side in my opinion.

[email protected] is great

Zed Shaw's Learn python the Hard way is good

Alan Gauld's Learn to program site is great

I find Why's guide both outdated and discursive to a harmful degree.