He sounds like a sad, lonely, clueless man.
He might be so clueless that he thinks he's flirting in an appropriate manner.

His "technique" is pitiful and desperate. I'd be honest with him and tell him that his comments are inappropriate and worrisome. I wouldn't be alone with him. If you do decide to meet him, I'd do it in a group setting. Don't invite him to your house. Be careful.

Note to all men: "Do you need a man in your life?" is an awful line. No, we don't need men. But, they can be a wonderful addition to our lives.