There is a healing effect to crying. It can be therapeutic. Jesus says the ones who weep, the ones who have something to mourn, are blessed. These are the people who feel the pain of the world. He is saying those who can grieve are the ones who will understand.
Most of the Fathers of the Church were great theologians. The problem with theology is that it stays mainly in the head. Saints Ephraim and Simeon were different. That’s probably why they weren’t as popular. While others filtered the gospel through the head, they filtered it through the heart. St. Ephraim says that until you have cried you don’t know God. They actually wanted tears to a be a sacrament in the Church.
We think we know God through ideas, but perhaps weeping will allow you to know God much better. Jesus praises the mourners, those who enter into solidarity with the suffering and not try to distance themselves from it. This is one reason why Jesus is so hard on the rich. Most wealthy people spend their lives trying to insulate themselves from pain. Mourning is a different reaction altogether. Those who mourn bear the pain of the world without looking for victims or perpetrators, but recognize the tragic reality that both sides are caught up in. They carry the dark side along with the light.