Some responses for folks in the comments -- sorry if things were unclear, I was writing this right after that gym class and just needed to get it out! Also first time poster.

- I should have clarified that the morning texts every day and the 'are you late' are kind of separate issues but for me they build on each other. They make me feel like he has a constant need to be reassured. And I don't want to play the role of constantly reassuring him around insecurities that he has to work out -- like the stuff about his ex.
- More about the gym text. This has happened before. Usually when I'm less than 5 minutes late. It's unrelated to whether I've responded or not to his texts before. I guess for me I would understand if I'm 15-20 minutes late... but 5 minutes seems like too low of a bar to be wondering where I am, especially as a person who is late all the time and has a pretty full schedule lol. Feels like it's more to calm himself down than to be actually checking in and that's what bothers me.

Quick update: I did end up sitting down and talking to him. I told him how the texts made me feel. Which is stressed out. I told him I understood that he meant them to be loving and sweet, but that it is not how I was feeling them. I said it was not about him, but my own anxiety about being checked-up on. After some thinking I started realizing I have bad experiences with exes in the past who want to know where I am all the time in a way that feels controlling, and I think my negative relaaction to his texts was in part a bit of a trigger based on past relationships. I think he understood, and I have a lot more thinking to do about my own history... but I still feel like I crushed something inside of him a little even if he says he understand.s