Not that I'm complaining mind you. I've been very happily married for over 30 years and raised three good kids. I've had a good life. But the "what ifs" still occasionally bug me decades later.
I feel the same way Mallory, I'm happily married and have four wonderful kids, but I still think about this girl in high school.
We were in the same club in high school and she first caught my attention at the end of my sophomore year. We were doing a scavenger hunt in the mall (got kicked out too, didn't know we weren't allowed to without permission!) and she said, "Hi" every time she saw me, but I didn't think much of it.
She was a year younger than I, so we never had any classes together and not much chance to talk, other than trips I took past her locker before heading to my first period class. One time, she was excited to see me and show me that she got a car.
I never pursued anything, hoping that a huge sign would come and carefully keeping my ear open for news if she had a boyfriend.
I kept in touch with her partway through my freshman year of college, but stopped when she mentioned in one e-mail that she had a boyfriend. So I kind of regret the e-mailing, maybe it would have been better not to know that, I don't know.
But, my wife and I got together during my sophomore year of college and 10 years later, we're happily married.
More practical regrets include not pursing a teaching degree (I teach now and thankfully Florida had a program for those who do not have teaching degrees to get certified). It would have been easier to get my degree right out of college and it probably would have saved me from being in two dead end jobs.
Lastly, when we moved to Florida, we had a good amount of money from selling the house up North. The market back in 2003 was just getting crazy, and we bought a cheaper house to save money. We ended up blowing through the money pretty quickly, spending in on non-essentials. Looking back, we wish we built a custom house, instead of the one we did, and added a swimming pool.
C'est La Vie.