Long, rambling story incoming but maybe a good payoff for someone feeling weird about skating alone...
When I first got back into skating after a loooooong layoff, I only skated alone out of pure ego and insecurity.
When I was a younger fella, I was pretty fucking good for my time and place.
I didn't have sponsors banging down my door or anything, but I was pretty well respected in my area.
Enough that local kids who I'd never met would know who I was on occasion. "Hey! You're ____, right?"
When I got back into it at age 39, I was decidedly not the local hero I once was. I was struggling to kickflip on flat ground but still had the mentality of a 19 year old kid who could kickflip a 10 stair. It was a hard pill to swallow and I was embarrassed in my own skin. It was so ridiculous in retrospect. Did I think I'd pick up where I left off 20 years ago??
So I skated alone, only going to the park at 7am or so for the first year because I was an arrogant dipshit in a midlife crisis and I couldn't handle not being the best skater at the park. After I got a few tricks under my belt again (and after getting sick of waking up at 6am on Saturday) I started hitting the park in the 9-10am time slot. That's when I started running into other early-AM skaters. They were always very polite, humble and fun to skate with, so after a few sessions of seeing these two dudes every Saturday morning, we exchanged numbers and decided to skate together.
We started meeting more solo AM skaters, and if we ever ran into the same AM skater a few times and they were chill and fun to skate with, we'd invite them into the group. Literally everyone we invited accepted enthusiastically.
We have a 10 person skate crew now, completely made up of random people who were skating alone on Weekend mornings.
We're all a little bit older, and we range in talent from flip-in/flip-out to just learning to 50-50, from pure street to mostly transition, but we're all kind and pleasant to each other and always have a great time.
So..TLDR...if you wanna make some fun, chill, accepting skate friends, hit your local park around 10am.
Skating alone can be fun, but it will never be as fun as skating with a crew, getting hyped up by and for one another.
And don't let your skill level deter you. A couple of us can flip into/out of grinds and slides, but when one of our homies landed his first 50-50 we all freaked the fuck out like he just won the super bowl.