Do you ever regret letting someone go? or turning them down?

Anonymous
this guy I work with we were talking at lunch today and he says he can't forget this girl he loved in college, he was mean to her and was a jerk and immature, but now he regrets all that and wishes he can go back to her, but she's moved on with another man. I was thinking...like is this a normal thing do people often feel this way? or do things happen for a reason? like they weren't meant to be?
Do you ever regret letting someone go? or turning them down?
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