Weighing the risks. Debating the pros and cons. He doesn't think he's helped her get any closer to an answer.

That's frustrating.

But this other part...

"If she hasn't shut you out, there's still time to do it. If she lets you be around her at all, she probably wants a relationship. Just... gotta remember it ain't about you. It's about her."

Look. He's obviously not a mom so he can't really relate to all that. But he did seriously damage a relationship and then realize it was one he wanted. So now he's trying to mend a bridge that only remained unburned because the other person is... unfailingly kind.

And for some reason saw something salvageable in the train wreck he used to be.

"When you reunite with her, make sure you tell her all the stuff you've told me. And give her time to chew it over. Don't rush her for a response."