If my lady friend were perfect, how would I be able to learn how to love?
Among other things, I would say spend time with mature Christian seniors who can help you grow as a person so you are more ready for a real relationship. So, you don't want older people who only sympathize with you and try to match-make; but share with ones who can see through you and help you with your good things and things needing correction for having a close relationship. And my opinion is a real guy can see through you, too, but will help you grow in Jesus. So, I would not go only by smiling
And if you discover you feel this guy is for real . . . I would say trust him by telling him. If you don't trust him, possibly God knows He does not want to assure you about him, and/or you are not ready for someone like him.
Possibly, he might be trustworthy and able to have compassion for you, but telling him how you see him might be a detraction, when you can simply enjoy and appreciate sharing with him.