He's a follower--something she doesn't have very many of. He gives her the positive attention she desperately craves. He's a troon, so she gets extra Woke Points for having him around and pretending he's just one of the girls.
Jude doesn't have many IRL friends, and given how touchy and controlling she is, she probably never has. So, online, she will take as a friend anybody who is willing to kiss her ass and not say anything that might upset her. Is it naïevete that keeps her from seeing what a creep and a loser this guy is? That may be part of it. But mostly, I think it's because he gives her good narcissistic supply, and thus she'll ignore his creepiness until he does something that offends her.
Jude's 23 going on two. Emotionally and socially, she's so stunted she has a lot more in common with those teenagers than with people her own age.
But teenagers are also naïve enough to actually fall for Jude's bullshit. They are much less likely to question her. They may feel like she understands them in a way their family and peers don't, so they will try to stay in her good graces. When you're 15-16, and someone in their 20s actually wants to hang out with you and be friends? That's like catnip to a lot of kids. And the narcissistic supply they give Jude is just as good as the troons, so she's not going to discourage them.
It's not even remotely about community; it's all about Jude getting the kind of attention she wants and being able to set all the rules for interacting with her. That's why she lets the troon participate alongside the kids, with no regard for whether it's good for the kids--it's good for Jude, and that's all that matters.