It proves how much of a moron he is. Naruto is the guy who will let you **** his girlfriend as long you remain his friend. He's an absolute doormat with no self respect.
I have no idea where you got that from.
First off, if Narutoʻs girlfriend was the kind of person who would have *** with other men, then sheʻs obviously not the right person for Naruto and doesnʻt really love him, and Narutoʻs better off without her.
Second, if you really were narutoʻs friend, you wouldnʻt have *** with his girlfriend.
So your scenario doesnʻt even make sense.
Next, why would Naruto shedding tears for someone like Obito mean that heʻs going to roll over for him and allow him to do whatever he wants? Does loving someone = you submit to all of their actions and allow them to do whatever they want? Obviously not. If Narutoʻs parents were alive and Obito tried to kill them, do you believe Naruto would just let Obito do it? Obviously not. Why do you think Narutoʻs going to fight Sasuke? Doesnʻt Naruto consider Sasuke a friend?
Naruto cried for an Obito who had changed from the guy who murdered Narutoʻs family into someone whoʻd willingly sacrifice everything he had for Narutoʻs life. Now tell me again, how crying for someone like that = youʻd let Obito walk all over you?