When taking care of business, you are primarily working with your rational, analytical mind to make decisions and address situations. It works to have meeting about such and such topic at 10:00 am on Tuesday, for instance. The rational mind or intellect is relatively detached from our emotions and can deal with the task at hand on demand.
But for emotional experiences, it is much more effective to address them when the timing and energy is right. It is important to discern the emotional energy of the person and yourself to see if it is conducive to such a discussion or experience.
So when you are wanting to address something with someone you care about, send out the intention, and then look for opportunities to present themselves to address or experience it. Trust your instincts to know when the energy is right. It is a matter of letting things unfold rather than forcing them.
Another skill to do this is to allow the subject matter that you wish to discuss to arise naturally. My Zen teacher would wait months for me to bring a topic up before he would discuss and give me counsel on it. That way he knew that I was ready and open to it. He found it more authentic to address things that were in the "present."
By finding the right opportunity, you will find the person you wish to connect with more open and available to what you want to share with them.