I don't know about the similar stages in life. It depends on your issues, I guess. My T is my age and I find that makes it difficult to talk about things going on in life at a certain age. I feel like she must have similar age-related stuff going on in her life, and I'm afraid of bothering her by talking about my reflections on that.
While writing this I realise that this would not be a problem if she would show a reaction, whatever reaction, sometimes. She's the kind of T that pretends to be totally unaffected, and exactly that behaviour gives me the feeling she actually disagrees. Hmmm. That says something about me, I guess.

I'm going off-topic, sorry!
So with a T in a similar stage in life, I clearly expect something like a connection on that stage in life. Since we don't have that connection, the similar stage in life feels more like a burden.