Hi Bear,
I think you can send messages at any time, especially heart messages of love. I didn't know that before I came to this site, although I really did. What I mean is, prayers for the dead are included in many other spiritual practices. Remembering the dead with respect, love and reverence has always been a part of many cultures.
For me, some of the greatest surprises are seeming contacts that appear spontaneously in my life in the form of dreams, waking messages or signs, and journeys in meditation.
I don't think there is one way....but if one way doesn't work for you, maybe just ask for another way. If quiet contemplation and prayer for a sign doesn't work, ask for a dream. Keep with the intent.
If that doesn't work, try meditating. A deep meditation will always give you some kind of message which you need to hear at that time, and is very comforting.
But I wouldn't expect a specific result at a specific time. Be gentle with yourself and let the messages come through when the path is clear.
I think you are on the right path if you just keep your mind open to possibility.
love, blink