Not sure how I feel about that

"Not sure how I feel about that."
Those are the words she said, but what I heard was more like, "I do not approve of that."
They sounded judgmental to my ears, almost like "I do not approve of you."

...

Different occasion:
"I'm not sure what to think about that."
Those were the words that came out of my mouth.  I did not mean them to be judgmental or disapproving, but I now realize that they may well sound that way in the ears of someone hearing them.  Someone who felt like I disapproved of them.

...

Two separate conversations.
Two separate issues.
Similar words.
Totally different understanding.
What made the difference?

 ...

Probably the main difference is that one time I was the hearer, the judged, from whom approval was being withheld.  In the other instance I was the speaker, and possibly the judge.

Is it possible that the first speaker did not intend to judge me? 
Maybe.  But I certainly felt judged.

Is it also possible that someone hearing the second conversation may have felt judged by me, may have felt the lack of my approval, even though that was not my intent?
Maybe.  I must admit that my words may have sounded like judgment.

...

Moral of the story:
Be aware that my words may come out sounding like disapproval even when I don't mean them that way.  Duh. 

Another difference could be the tone of the two conversations.  The first was full of questions - almost an interrogation.  The second was mostly listening.  Learning.

Yep, listening is usually a good thing.
I could learn to do more listening.