All men need a woman's human warmth while keeping their self-esteem intact. Always keep in mind that this is an adult and not a child, although sometimes he can be a very convincing baby!
Steps
Step 1. Don't make jokes
Saying "big crybaby" will not only make him feel less of a man, but he'll be angry with you later. A wounded man is vindictive!
Step 2. Make physical contact by putting your arm around him or getting close to him
You want to give him the impression that he still retains his status.
Step 3. Listen to him and don't interrupt him while he speaks
Step 4. Don't talk too much
Avoid saying "It will be okay" or anything like that. Maybe everything will be all right, but now is not the time for false promises.
Step 5. Remember that you want to reinforce his masculinity by creating a comforting atmosphere for a clearly afflicted man
Step 6. Take a deep, gentle sigh
Try not to overdo it; it should be similar to what you do after sending a difficult text or after a complicated conversation.
Step 7. Don't bring up difficult or painful topics
He will talk about it himself if you have created the right atmosphere. Eventually he will begin to feel totally accepted by you for who he is, not for what he does or what he gives you.
Step 8. Once you accept your man for who he is, he will be able to feel truly comforted by you, as he will know you have no double ends
Step 9. Tell him clearly that it is okay if he feels upset
Unfortunately, sometimes men feel like they have a duty to put on the brave man's mask and act like it's all right, because that makes them look strong. Make sure he knows there's nothing wrong with not feeling right, and that you don't have a worse opinion of him for this situation.