When people experience a loss, they go through a process of healing, which many times includes the need to cry. In these occasions, the best thing we can do is simply listen and allow the person to cry if they have to, while not trying to give them advice.
Usually, we think of hurt when we think of losing a loved one, but this same effect may be caused by different kinds of losses in life. For there is no such thing as a pleasant loss.
We hurt when a family member gets lost in alcohol or drugs, though they are physically alive, they are still lost, and therefore are not the same. The human being hurts when they lose their employment, a house, a business, their years of savings, or a good friendship. Children and young people hurt when they lose a friend because they have to move schools or move out of town, etc.
In times like these it is natural for a person to cry while they go through the process of acceptance, healing and re-adaption. This is where a good friend or mentor can help by simply listening and encouraging a person, not lecturing them.
It is not a weakness to cry. In fact, it is a strength to cry when it is necessary, and many times it is the only way to heal the wounds in our soul during the course of life. Therefore, cry when you are hurting.
Think about it:
How can you deal with pain when something is hurting you or someone else that is important to you like a friend or family member?
How can you be a best friend to someone that maybe is hurting at this moment?