Don't know what to do about this guy?

Ok so I'm a freshmen in a highschool and 14. Anyways so in our town for fun all the schools go to the skating rink and hang out on the weekends. So I me and my friends met this guy Dylan and he's all our best friend. So he's super weird and funny and I really like that about him but I always get to scared to tell him I actually like him even though we flirt when we hang. It's really weird I just really like him and he's so funny, but I always get to scared so he always gets a girlfriend before I can tell him and then I get so sad. I just do not know what to do I just don't really want him to see me as just a friend. So should I dress more provocative should I flirt more. Ugh what should I do. I'm dying 😞