Firstly, because flip flops are comfier than heels.
He may be flip flopping because he wants to like you, especially since you guys are such great friends. It seems to make sense that good friends should equal good partners, but it often doesn't work like that. There's probably attraction which gets you together over and over, but when you try it, it doesn't work how you want it to.
So if you think you're never going to get over him, and that he'll never commit and settle down, then either suck it up and just be friends, or end the whole thing.
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