My youth pastor did a masterful job of explaining what it meant when Jesus cried. Below is what he said (paraphrased).
"In John 11 we find the story of the death of Lazarus who was Jesus' best friend. And we're told in verse 35 that when He got the news of the passing of His friend, that "Jesus wept." Now there are basically two schools of thought on this; first that He shed a couple of tears and then went on about His business. Second was that He had what we might call today an epic crying meltdown. Either way He cried and that's instructive to us.
You see, Jesus didn't hope that everything was going to be okay concerning Lazarus, He knew it would. He knew it would because He knew He was going to make it okay by raising him from the dead. Yet He chose to cry anyway. Why? To teach us we are to respond to hard times and sad times we may face. Jesus was perfect. He never lacked faith. He was never weak. He was never immature. Yet He chose to weep bitterly, He deliberately and purposely cried His eyes out to teach us that when we get bad news, it's okay to use our God given emotions. Have a good cry, then if it is within your power to do so, after you've cried, get up and go do something about the situation. If there is nothing you can do about it, then trust Him with it. And even in trusting Him, it's still okay to cry. Our tears are a language He understands."
Many of today's "men" have no concept of actual manhood. All men are males, but not all males are men. Maleness is function of birth. Manhood is a choice. Many of today's alleged men have been conditioned and programmed by a godless society and culture to believe the lie that says for a man to cry, to show emotion, or to show affection is somehow weak, immature, and shameful. The opposite is true. For a man to cry, to show emotion and affection is an indication of strength and maturity. It is something to be embraced and celebrated.
I'm a man, 23, and I am not ashamed to admit that I cry. I cry easily, often, and for a variety of reasons. And I am okay with that. In fact, I'm crying now and I don't care who knows that I am.