OP, I get this and feel it hard. I've considered the trauma I've felt over past relationships more difficult to get over than the traumatic things I've experienced that have conspired to take my life. I also know that the regret we experience over the chances we never took far outweigh the regret we experience from taking that shot and failing. Living with the "what if?" still plaguing your thoughts is a tough one.

Folks will tell you to move on, but I know it's not that simple. You're currently processing the very real possibility of not only never being able to answer that "what if?" question, but also losing a friendship you've had and valued for years. I don't think there's an easy or best answer here. If you meet and she says she can't talk to you anymore, you will have to choose between keeping your feelings and thoughts to yourself - you will likely hear this is the mature choice - or telling her how you feel - which is still a totally human choice, though folks will tell you it's selfish. (Try not to think of it as that way as we should consider our own wants and desires in order to be happy in life.) I've been there before and took the latter route. I don't regret that decision. We had a great romance, got married, and tried to start a family. Unfortunately, a medical condition I discovered later in life prevented us from having children and she moved on. As others have pointed out, people often eventually develop the drive to settle down, and ultimately the same doubts that drove her hesitation early on resulted in the irreparable fracture that ended our marriage. I kept this irrational belief that it would work out again like it did before, but I got cancer while we were separated and that sorta solidified things for her. No point in holding out hope to start a family with a guy who can't have kids and will probably be dead soon. She found another guy pretty soon after we separated and got pregnant before the divorce papers were even drafted. We said we'd stay friends, but I haven't spoken with her in over a year at this point. She will never know the things I wanted to tell her, the life I wanted to live with her, or how much she meant to me. I've seen her posts on social media. She has two kids, a loving partner, and both of their families adore them. She is content in life, having finally found the family and stability that she always longed for and that I objectively would never be able to provide. Though I feel robbed of the life we had promised each other, I am happy for her and do not blame her. This time, I took the former choice. I didn't want to blow up her life when I couldn't even guarantee I'd be alive in a year, and who was I to potentially rob her of what she had wanted for her entire life and that I could never give her? This is a regret, a "what if?" that I will carry with me to my grave. I still think I made the right choice for me in both cases, though I know she wishes I would have chosen differently the first time around due to the outcome and pain involved.

Ultimately, there is no right choice here. It is impossible to know and plan for all potential outcomes. You just need to decide what type of regret you are most willing to live with.

I feel for you, OP.