[advice] [relationship] How to get with a semi-long distance friend when your parents are totally not on board with it???

Hi so I'm a 16 year old girl and I have a friend (17M) who lives like an hour away from me - we see each other a few times a month in the fall/winter/spring and then multiple times a week during the summer. We're pretty good friends (social media is v helpful with staying in touch) and we used to be super close because we both got bullied by the same people; although I don't get bullied by them anymore, unfortunately he still does. He can be a bit socially awkward sometimes but I think it's cute honestly. He's so sweet and he tries to be friends with everyone (even though people keep making fun of him). People ship us, which I think is funny, but I can't tell what he thinks about it. Our parents are really good friends, but my parents don't like me talking to him without both sets of parents knowing (long story). But I think it's worth a try even if my parents aren't happy with it. I used to like him about three years ago, I thought I got over that two years ago, but clearly that didn't happen lmao.

I want to subtly flirt with him, just to test the waters a bit, and figure out if he's interested in me in that way. I know he's not the type to take hints but I don't want to be super obvious about it. How do I do that if we don't see each other face-to-face very often? And when we inevitably do see each other this summer, how should I flirt/try to see if he's interested, without other people noticing and making fun of him or us?