WB, I know the dilemma. Ennui, regret, the existential crisis of not following the other path, that inkling of the 'mid-life crisis.' I know because I feel like that sometimes too. Back in the day I used to party a lot, and hung out with a group that always partied a little too hard. I've talked about them a little here, and how many of them have passed on already. But it's the ones that are still around that make us sit back and look at ourselves.
We change over time. If we didn't, we'd be pretty damn boring. But as we change, so do those around us, our friends and family and people we love. They change as well. Sometimes that change means growing apart, which is okay. For example, I haven't seen my best man face to face in over 10 years and it's been at least 5 since we last spoke more than a few sentences on some FaceBook post. I absolutely loved this dude, but he took a different path than I did. I moved to the city, got married, had kids. He stayed out in the sticks, dropped out of school for the third or fourth time, got caught up in some local drama and jumped on the MAGA wagon. Last I heard he was living with a woman and her kids and ran a donut shop of some kind, but it's been so long since we talked and had a real conversation, I don't know if it would be possible to go back. I hate that we've grown apart, but I also know that I couldn't follow his path and he wouldn't and couldn't follow mine.
As far as regrets go, that's healthy. I love my family more than anything else, but I don't know if a day passes where I at least have a fleeting thought of what could've been. According to the Copenhagen Model of alternate realities, each and every possible action happens in another universe in the multiverse. And with how mind-boggingly big infinity really is, there's an infinite number of universes where I didn't ask my wife on our first date and instead asked out the other girl I was talking to at the time. Same with every other choice I've made, from kissing a different girl to saying "why not?" when that guy at the NYE party wanted to take me to his place. There's an alternate reality where right now I'm Batman and I'm balls deep in Allison Brie. Of course, the odds are likely that in that universe I'm high as a kite and she's Aly, the toothless overweight chick down at the 7-11.
Same as there's a whole slew of infinite worlds where you stuck around with the old crew. But knowing what you know, would current you want to hang out with old you and your old friends? I mean, old you prioritized having a kid and raising a family over partying every night. What do you think the you that followed that path is doing right now? That you probably has his regrets, too.