I like this guy and we are close, but not dating. He's older than me by a fair bit, and our families have known each other for a very long... Show More
Most Helpful Opinion
It does make a lot of sense. Do go about comforting him but with logic not just caring words. If he is upset about how he is..point out his goodness to him.
Tell him no man is perfect. Then advice him to do things which would help him be what he wants. DO KEEP IN MIND. COMFORT HIM WITH LOGIC NOT JUST MERE CARING WORDS.