Most Helpful Girl
YES, it is EXTREMELY creepy and weird. He is damn near 30 and he's showing a romantic interest in someone who hasn't even finished high school -_- Someone who's still processing puberty. Someone who hasn't even entered the realm of adulthood. It's a red flag.
If a 26 year old ever messed around with my 16 or 17 year old kid sister, cousin, or friend's sister, I'd have my eyes on him like a hawk and make sure he pays if he does anything even mildly inappropriate...3