Having problems crashing IDLE

[Quintessence]

I've been learning Python over the past week or so and I keep running into an issue where opening saved files will crash IDLE (not consistently, sometimes the same files with no changes will open and sometimes not). I was originally running Python 3.2.3, but I removed it and upgraded to 3.3.0 hoping to resolve the issue (but to no avail). While troubleshooting, someone suggested I try opening IDLE via command prompt. When I do that IDLE never crashes, but It does show this error (screenshot):
http://i.imgur.com/1JqiRsY.png (3.2.3)
http://i.imgur.com/5KxE88K.png (3.3.0)


Some additional info:
- When IDLE crashes it does not display an error, every open window simply closes.
- IDLE has never crashed after opening a file when I open it via command prompt, even if it was previously consistently displaying that behavior.
- I am running Windows 7 x64 with all updates.

Has anyone ever encountered this? What does the error mean?