Best friends to.. maybe more?

So I met this girl 14 years ago when we were in Grade 6 and we hated each other. When we entered grade 7 we became best friends and then grade 8 I asked her out, and we dated for like 2 weeks then I did something horrible- I dumped her because my maw best friend at the time wanted to take her to prom. I didn’t think anything of it, but I think it really hurt her and she still mentions it every now and again (I do feel horrible looking back)

So in grade 10 I asked her out again and we dated again for a few months then I broke up with her because I liked another girl (she didn’t talk to me for a while after this one)

and then grade 10, same thing, asked her out and then broke up with her cause I fell again for the same girl that I broke it off for last time (again, she didn’t talk to me for like a year)

after that year passed we just managed to stay friends and recently (the last 2 years or so) we got really close again and I realize how but I treated her in the past and that I really regret breaking up with her the first time because I honestly think we would have lasted.

We recently (a few weeks ago) went away with some friends for a long weekend and her and I stayed up with 3-4AM every morning while Everyone else was asleep and talked and shared so much and I feel like we clicked.

Now, she’s never been the type to talk An out relationships and stuff, every now and again I’ll mentioned in a joking fashion that her and I will get married and have this perfect life and she adds to it but other times she just ignores it or tries changing the subject so I’m really confused…

Should I try to shoot my shot. Or let this fantasy die and keep the friendship? HELP!?!

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