So I've known this girl for quite a while and we've seen each other grow up, but we haven't really talked to each other its always been with other people.

We've known each other since we were 14 and I think it would seem weird if I started hitting on her out of the blue especially since we've never really talked but known each other for so long.

I'm her DMs at the moment but the conversation is a little bland because I dont know what to say and I dont know how much I should flirt. How do I test the waters? She doesn't ever leave me on read, but she doesn't exactly eagerly wait for my message (I wouldn't expect her to).

How much should I flirt? I have no clue, is it strange? - it feels like we've known each other forever. How do I test the waters? What should I talk about?