He's not a creep, but he has the emotional intelligence of an insurance investigator.

"Hi, you sound needy and vulnerable" is a rough starting point for a pickup line. He clearly didn't mean it as an insult, but it's not hard to imagine a woman in that situation being embarrassed, feeling exposed, and being insulted by the implication that this guy might be trying to capitalize on her moment of vulnerability.

Hurt-people hurt people.