Sorry about the late reply - this came up in one of those list of random follow up questions.
> how often do you regret ...
Sometimes.
If it is a breakup because she broke some important value early in a relationship (eg fidelity, not being racist), then there is little emotional capital invested, whether or not we had sex, so I'll end it quickly, telling her why so there is no lingering doubt about reconciliation on her part, with few regrets.
A couple of times I broke it off after an extendended relationship, in one case including about a year of living together because we just had very different goals in life. In both cases she was a fantastic girlfriend who another guy would happily have spent a life with. This caused them both some pain which is not good, and I did not do lightly. I did try to explain why as gently as I could, over an extended time and tried to be supportive of them through a change I had to make. I still (27 years on - my profile is wrong I'm mid 40s) regret the upset I caused them.
The good ending is that both happily married and have been in lifelong relationships with family etc since (as was I until my wife died a couple of years ago).
When handling the breakups I looked back to what was hardest for me to cope with the two times someone I loved dumped me as a late teen, or early twenties person and tried to do the opposite out of care for people I still respected, but with regret no longer was in love with.
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My experience has been that it depends on how long we have been going out, how close we were and the reason for the break up. I got over all of them pretty fast except one which took me a year.
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Never, each relationship that I actually valued was ended by her not me. I only break up with people I don't care about which means I never regret it.
Not very often. It's good reasons that guys do it.
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