Stop with the league nonsense.
No one is out of anyone's league. There are no leagues.
Don't make every conversation fraught with meaning. I suspect that's what is making you nervous.
This is why small talk exists.
"Hi, ____, how's your day going so far?" "Do you have plans for autumn? Doing anything fun?"
Oh, and when she's with her pals, talk to everyone. She's had her friends a lot longer than you've liked her, I bet.
"Hey, ladies, you're all looking terrific today. " "Sorry to interrupt your conversation, but I'm asking this question for science. What's the worst poptart flavor...ever?"
Be nice. Be funny if you can. Be respectful.
You can do this.