[header] How to have a deep conversation [title] Find the right person. [step] Sometimes, chemistry plays into the depth of connection between two people. If you have been trying and failing at engaging in deep conversations, it could be because you are trying with the wrong people. 
Look for other people like you who thrive on deep conversations. [substeps] A " deep " person may be very curious, thoughtful, open-minded and show excitement when discussing topics that go beyond the surface.