All the time. I have never had to luxury of not having to have deep conversations due to the utter fail that was our upbringing with my mother.
So, conversations with her included asking who our fathers were, if we were going to continue living with her, why we were moving, why we were moving back with her abusing boyfriend, why we couldn't join the school band, why we wanted to go to school/church/anywhere, etc.
During living with her and after, there were long conversations with grandparents and great grandparents, and neighbors and friends' parents acting as substitute parents and counselors.
All during my life with Grandmother, I had deep conversations with her about science, religion, family, society, law, psychology, genealogy, cinema, anthropology, death, debt, horticulture, music, psychology, marriage, family, and our immediate family.
Also, I met with my aunt and uncle a few times and stayed a weekend or so, and we talked long into the night.
My eldest sister is seven years older, and has long acted a matriarch in our family.
These days, I have long conversations by phone, text, and in person with my siblings and cousins.
We are a family that has always communicated. It runs the spectrum of topics and emotions. Sometimes it's joyful, sometimes tedious, sometimes annoying, and many other emotions.
Are you going to share your basis for asking? What happens in your family?