Windows of opportunity aren’t open for long. If you wait too long to make your move, that opportunity will no longer be there, and you’ll be kicking yourself for not acting sooner. Whether it’s buying something you really wanted or chasing after a girl, the principle is still the same.
The regret here applies to the missing of the opportunity and the hesitation that preceded it. Let’s say you didn’t miss that opportunity, but the result of it was less than desirable. That could also lead to regret, but for a different reason altogether (unfavorable outcome vs not taking the chance to get to that outcome, favorable or not).
When people say they live their life with no regrets, I’d like to think that they’re full of sh!t. I find it hard to believe that a person can live a perfect life and not have changed anything, that they were SOO sure of themselves, in every decision they made, that they never missed any opportunity to somehow improve their life (or not). I just don’t believe such a person exists. Then again, I’m more pessimist than optimist.
Oh, and this really doesn't apply to anything of any importance in my life right now, it's just that I think about a lot, and when I do it makes me reminisce the experiences in my past where this applied.