Maybe I'll talk to T about it this week. That's probably a better option than trying to force myself to cry or trying to only talk about things that make me sad.

I think crying would help break down any barrier that I unconsciously put up between T and I, allowing me to open up even more. I've only broken down while talking to someone once in my whole life so it's not something I'm good at.
I also think I need to in order to fully process some childhood trauma that I went through. I don't always want to talk about it because I think I've moved on but I still think about it a lot so it clearly hasn't been fully resolved.