This guy is a chronic people pleaser.

She has moved on, but the silence is making him anxious that she is mad at him.

This isn't about her. It is about him feeling guilty.

His story about her being possessive doesn't match his actions of texting her weeks after the breakup.

Why would you want to stay in contact with someone who made you unhappy if you didn't need to?

You are not naive. i think you are the more mature one.