Not everyone likes or wants to be “looked up to”. Sometimes it’s a lot of pressure for someone when a person looks up to them and they just don’t want the responsibility.
If a person has a boss they look up to for career reasons like they want to follow in their footsteps to advance their career then that’s different. But what you describe is not like that and people just don’t want to be that person for you.

A few years ago I had a “friend” who was constantly “up my butt” so to speak. She always wanted hang out (like every day). Talk on the phone constantly. I would get several text messages from her daily. I couldn’t be there for her all the time in that capacity. It ultimately cost her the friendship because she just didn’t know when to quit. I didn’t want to be a mom like figure to her. It was too much pressure.

Try thinking about how the other people feel in these situations. If your boss flat out told you he feels creeped out then maybe you can just try to back off a bit. Don’t even try to discuss it with him. Maybe a simple “I’m sorry you feel creeped out. I’ll back off” and be done with it. You probably further creeped him out by going there on your day off.

Does it cause anxiety for you when someone puts up a boundary?

What does the therapist say when you tell them this stuff? Are they helping you try to see how your patterns are repeating?