Yeah, I've reversed course on both those things now. I literally just tell my spouse, "I think tonight at 8 I'm going to go see Project Hail Mary" since I'm the only one interested in that kind of movie. And dine wherever I want when I'm alone.
I think it was a lot harder when I was 18 because I saw being alone as a reflection on my worth as a person.
I was on the college's film committee and I often enjoyed hanging out with some of the other members on a weekend night especially if I didn't have anything else going on or it was later. (We also pre-screened all of our films in case there a problem with the print. So I did that too sometimes.) I was also fine, if I had a free afternoon with going to one of the discount theaters in town if there was something I wanted to see.
But, yeah, looking back I think I was a lot less inclined to just eat by myself in a restaurant--partially because I could often rope someone else in or would know people if I went into a dining hall and partly because I wasn't accustomed to just having a meal without anyone else around.
I always recommend people to go to a theater themselves, it is really an enjoyable time. Some people act like you are crazy when they hear about it, but everybody already watches tv shows or movies by themselves.