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I'm so glad that you posted this. I had a similar experience. My personal goal is to ask some things only twice, and then suck it up and move on.
The girl I dated in high school broke up with me when college started. A few years later, we were talking again, and we were in the friendship fog. I asked her out again, she said no. That also hurt like hell, but I told myself I've asked twice. Time to move on.
I actually recently found a journal entry from that night - "It feels like I am king of the friend zone with her, but holy shit it feels so good to have that cleared up, and now I know I have a solid friend who I don't have to worry about dating potential".
After that she was the first female friend who I didn't constantly have a thought of "...but what if?", and that was incredible.
Over 10 years later, she's like a sister to me - she was my best ma'am at my wedding, and I was a bridesman at hers. (my wife likes to poke fun at the imbalance here, but we had a small wedding haha)