It’s not good to ask for signs, because you’ll go crazy trying to figure them out. (Ask me how I know…)
Sometimes, God sends little messages in the ordinary, though.
For example-- I remember when JPII was ill and about to pass away. I worked across the street from the cathedral at the time, so I remember going in over lunch to pray for him. I often went to lunchtime Mass, and I always sat in the same little pew. And so I went to the same little place I had sat over a hundred times before and prayed-- for JPII, for the Church, for his successor, for the Cardinals, for the Conclave, for everything. But mostly for him and the Church, because as the second-longest-reigning Pope, we had all gotten pretty used to having him around, right?
So, while I knelt there on my kneeler, I happened to look down at my hands. And, perfectly reflected in the flat surface of my engagement ring, was a stained glass window over the sacristy door that I had never paid attention to. It was a chalice with the eucharist over it. And basically, the message I got for my prayer was, “Popes may come and go with their time, but Jesus is always present in the Eucharist, and the Church is the Body of Christ, and it won’t be abandoned.”
Which was a pretty cool message to get.
I would never have asked, “Hey, God, I’m gonna pray to you about something, and I want you to tell me what to do.” But it was a nice little gesture, and I appreciated it.