Oh god it’s the ghost of online relationship past. Apparently kids are the same 20+ years later.

In my experience, yes those are red flags, and this is NOT a good situation. You mentioned his age but not hers but I’d bet dollars to doughnuts she’s younger than him.

Listen, I know from personal experience this relationship is a bad Idea and Aunt Weariedfae says get out and do not feel bad about it. She’ll realize later how manipulative it was. That the power balance was way out of whack. What controlling behavior is. I think he did your friend a kindness by straight up admitting he wouldn’t visit instead of scheduling trips and canceling last minute over and over.

I’m sorry your friend is in this situation. I also don’t think your friend may listen to advice about decoupling. But maybe she’s smarter than myself and my friend who also went through the same thing around the same time. Hopefully she is.