While I'm not one to live my life based on the "could have, should have, would haves", I do find myself wondering what would have happened if things had been a little different during some situations!
For instance, when I met my husband for the first time, 17 years ago, I was in a REALLY bad relationship that he ultimately got me out of. But I wonder what would have happened if that relationship wasn't a bad one. I knew the moment I seen my husband for the first time that he was going to be someone important in my life! And here we are, 17 years and one week after our first date, still together. I am VERY blessed to have him in my life and I love him with all my heart "most" of the time...LOL!
Something more recent that I think about is should we take the risk and apply for mortgage quotes in an attempt to buy the house we're currently renting? Yes, the asking price for the house is quit a bit higher than what it's worth or what the payoff is. But I have a feeling if we were actually in the position to make them an offer with approval in hand, they'd lower that price. Our landlord knows how much we love living here and how much we don't want to move. He let us know when the for sale sign went up that he didn't want us to move! But I also know that we're not in a financial position that would make it possible for us to be approved for a mortgage right now.