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I've had maybe 6 people that got away who I could have had a better relationship with than most of the ones I already have had.
Thankfully one of them is still a good friend of mine, we just mesh well in behavior and understanding eachother. Unfortunately, it was a case of her being too reluctant to have taken a chance with me when I broke up with one of my exes some 14 or so years ago. Since then, she's been with someone new and while it's been going well. But we've talked at times about how we could've been if we were theoretically together.
And nothing feels worse than not only knowing you could've had them if they just spoke up, but knowing all this time later and not having a crack of a shot to try. It just sucks.