Advice needed for this girl (Shy)

Thanks for the tips!

I would never do anything through family.....ever.

Her mom noticing your single doesn't mean shit for her. Socialize with the girl, show her you're a normal human being, and take off the pressure of "oh but everyone thinks you two would be a great couple" that seems to be going on. A lot of her behavior seems to be her passive aggressiveness to fight the matchmaking thats going on without her consent. So, be social with her, show her you're a normal human being & don't bite, but help her have a fun time, if she's interested, you'll pick up on it, if she isn't, at least you're clearing up the weird vibe.

Also, stop obsessing over women see twice a year.