Struggling to Find Courage

So every year in the fall I get super interested in dating and flirting. Last year I had my sights set on dating this girl I met, we went on some 'dates' but we didn't call them that and I didn't push anything. As winter subsided my interest waned and I told her she would look good with another girl she had seemed to be talking to(Literally the worst decision ever). So now here we are and it's fall again and we've hung out multiple times and I want her to be my first kiss, at the very least, but I can't find a way to make it happen, I'm incredibly shy and she's not extremely intiative in terms of relationships which is making this all so hard. Tips?