Biggest Regret(s) of Your Life

[GabyKeepsMeWarm]

Young guy at work has kinda taken a liking to me lately. He found out about my “former life”, and he’s been filled with questions and always chatting me up.

He’s a good kid; bright, handsome, and hopefully doesn’t fall into the trappings of life before he even has a chance to get started.

At any rate…. While sharing some stories, I fell upon one that turned into my total regret, combined with rummaging around in some old boxes where I found a few “treasures”, an old photo of my dad with me and my siblings. Been looking for that photo for a long time, and it’s more special after my dad’s passing a few years ago. Found my old Blockbuster member card. An old flyer from my band of 20+ years ago. A huge chunk of ticket stubs from movies and shows I went to from the early 2000’s. And a buttload of old call sheets from the first movie I worked on. Then I found an unopened card/letter that was meant for Spencer Grammer. My heart sank.

I briefly dated her in 2001/2002. We worked together at first, and I was her trainer. We had immediate rapport and chemistry in spite of our age difference. She was only 18 and I was 25. We’d worked together for several weeks before I discovered she was a star’s daughter. Was a busy Saturday and I’m working the info stand, customers everywhere, and I’m locked in on the search computer when I hear her familiar voice, “Hey Tom! Just wanted to say hi! And this is my dad!” I no longer than have the words, “hey Spence”, out of my mouth and there’s Frasier ****ing Crane. Oh. Right. Grammer. Well **** me…

Things were pretty much normal for the next several weeks as we worked aside each other. We were closing together one night and it came up that I had a bootleg DVD of Royal Tennenbaums. She hadn’t seen it, and asked if we could hang out together after work and watch it at my place. Folks, I had reservations knowing her age, but **** it, it’s just watching a movie, right? Well, we’re about 30 minutes into the movie and she puts the moves on me, flat out asking if she can kiss me. So yup. You can imagine how that played out. And it played out again several more times over the following weeks. And it was great. We got along perfectly. No games, no arguments, just pure chemistry.

And then she was going to take off to NYC for a couple months for classes…. And during this time I ran across an online article with her and her dad and according to the site, she was only 16 years old. I FREAKED. I ghosted her completely. She’d call, I never answered. Emails. Nope. Finally talked to her after hearing she was in a serious car wreck and I told her that we couldn’t see each other anymore. Well, turns out the online article’s dates were wrong, she was in fact 18 turning 19, and while it was maybe a slightly inappropriate age gap, it wasn’t illegal, and I wasn’t a sicko getting hunted by the FBI.

I ****ed up. Colossal **** up. I’ve found love a few times since. Plenty of relationships. Nothing has ever worked out. And now I’m middle aged and still single. I haven’t obsessed about her or thought too much about it, but yeah, I regret how that played out. I was naive, listening to my friends too much and not trusting myself enough at that time. I’ll never know if we could’ve continued to be a couple, but I’ll be damned if I haven’t had several moments of wondering what could have been.

Second worst regret…. I’m ashamed to admit I got a DUI after graduating college. Was on my way from the bars with a buddy to grab a bite to eat and “sober up”, but I was driving 7 over the limit, got popped, and spent the night in the pokie. Mom picked me up the following day and her favorite cousin had died the same day. I wished the world would just swallow me up. I spent a good chunk of all the money gifts from graduating college on paying fines, and I don’t think I’ve ever been more ashamed in my life.


So what about you CPer’s? What are your most regrettable moments?

[BlackOp]

Ruff guess...but I'd estimate 98.9% of the responses will involve a woman...not buying Apple stock is a distant second.

[notorious]

Gabbykeepsmeselfreflecting.

[duncan_idaho]

Biggest regret (out of my control): Being homeschooled in high school. For a lot of reasons, but the biggest being that I didn't get pushed to persevere through things I didn't get right away (hello undiagnosed-until-41-ADHD). It affected what I studied in college and the career field I went into (I went into something that was easy for me, that I was naturally good at). I should probably be an engineer.

Biggest regret (circumstance):
In 2003, before my junior year of college, Mrs. Idaho and I were at the same house party. I had recently broken up with a long-term girlfriend, and I was on the prowl. Our paths didn't cross at the party, randomly. I met someone else and dated her for most of that year of school. It left me with some scars that almost entirely screwed up things with Mrs. Idaho.

I'd give a lot to have one more year with her.

[DJ's left nut]

That I never Served.

At the very least, I went to Law School to go into the JAG corps. Got waitlisted, took a job. Got accepted but felt I owed it to the firm that took a flyer on me to play it out. If I wasn't going to grab a rifle and stand a post, I should have at LEAST done the Jag thing.

But inertia took over. I've done well enough and things have turned out pretty nicely for me (most days). But I can't imagine even a short term in JAG would've changed things THAT much and maybe I'd have gone career. Hell, I'd be nearing retirement eligibility as a Lt. Col at worst right about now.

{shrug}

Also wish I'd have left the state for school at least once. Undergrad doesn't bother me much -- that was free college, seemed silly to turn that down. But I had some pretty nice little acceptance letters from schools across the country for law school and I just kinda let inertia and a little laziness win that battle again. Didn't feel like going through the headache of moving to NY or NC or Texas or Colorado or Massachusetts (funny enough, with a handful of top 50 schools accepting me, it was the damn party schools in AZ that said thanks but no thanks; I'll always kinda get a kick out of that...)

So again, I took the scholarship and the simpler route. At some point I should've grabbed my nuts and gotten out of the midwest for awhile. Or at the very least gone to Wash U, paid a hell of a lot more but I'd have had to push myself harder.

I think my issue was a realization that I can do well at about 70% effort most of the time so that's just kinda what I did. And eventually you're gonna find yourself wishing you'd have maxed out a bit more at least a time or two.

[InvinciBill]

I found Cave/PatMahomesIsGod's biggest regret:

https://onemileatatime.com/news/amer...-fatally-shot/

[SHOWTIME]

not investing in BTC early on...

[ChiefsCountry]

For me personally not going into law. Should have went that route for a career. Always thought it was just the Johhny Cochran or ambulance chaser types instead of all the different avenues you can specialize in.

My great uncle had an even greater one. He was friends with Bud Walton. Bud and Sam would come out and bird hunt all the time at his farm. They wanted him to invest in their new venture a discount store in Arkansas. That discount store became Wal Mart.

[George Liquor]

Not buying BTC when I first found out about it. I could be chilling on the Adriatic coast instead of sitting in a factory shitposting.

Had the money to get it all solved in my twenties.

[DJ's left nut]

Originally Posted by ChiefsCountry

For me personally not going into law. Should have went that route for a career. Always thought it was just the Johhny Cochran or ambulance chaser types instead of all the different avenues you can specialize in.

My great uncle had an even greater one. He was friends with Bud Walton. Bud and Sam would come out and bird hunt all the time at his farm. They wanted him to invest in their new venture a discount store in Arkansas. That discount store became Wal Mart.

So when did your great uncle eat a bullet? Yikes -- that's a tough blow...

Weirdly, I was an acquaintance of one of the guys who was involved in starting The Players Tribune. It sounded like a neat idea that I never thought would get very far. He wanted me to be an editor for them but at the time it would've been one of those unpaid things that looked like a whole shitload of work in my off-hours as I was starting a family. It would be (essentially) unpaid and I was pretty sure I'd be doing it for a year doing nothing but reading trash articles from minor leaguers because this guy didn't really seem to have any 'ins'. I passed and a couple years later you have HoF players announcing their retirements with them. I guess he ended up locking in with a big agency and got Jeter on board and things progressed pretty quickly from there.

So...yeah. Oops. Probably should've taken him up on that one.

[notorious]

Not signing up for Chiefsplanet sooner.

[Dartgod]

Not many really. Probably the biggest is not saving money when I was younger. Sure, I had a lot of fun, but it sure would be nice to be able to retire now.

The other one is that I don't have a single picture of my '72 El Camino I had 40 years ago. Damn that was a sweet ride.

[Indian Chief]

I think the closest to a regret I have is not knowing what career I wanted to pursue in undergrad. I ended up completely changing careers around 30. Truth is though, I currently have a job that utilizes both backgrounds, so it's hard to say where I'd be without that experience.

[IowaHawkeyeChief]

Originally Posted by BlackOp

Ruff guess...but I'd estimate 98.9% of the responses will involve a woman...not buying Apple stock is a distant second.

now that you mention it. I did own 37 bitcoin in 2014...investor in a mining operation my uncle had... did OK and made some good money, but man oh man, if I could have imagined...

[ChiefsCountry]

Originally Posted by DJ's left nut

So when did your great uncle eat a bullet? Yikes -- that's a tough blow...

Weirdly, I was an acquaintance of one of the guys who was involved in starting The Players Tribune. It sounded like a neat idea that I never thought would get very far. He wanted me to be an editor for them but at the time it would've been one of those unpaid things that looked like a whole shitload of work in my off-hours as I was starting a family. It would be (essentially) unpaid and I was pretty sure I'd be doing it for a year doing nothing but reading trash articles from minor leaguers because this guy didn't really seem to have any 'ins'. I passed and a couple years later you have HoF players announcing their retirements with them. I guess he ended up locking in with a big agency and got Jeter on board and things progressed pretty quickly from there.

So...yeah. Oops. Probably should've taken him up on that one.

Tough regret but he lived a great life up until he passed away at 95.

Mine for investment was when I just graduated high school. Summer of 03, had an old guy come into the family business. Was talking to him, he told looks like you just graduated probably got some money right now. I told him I did. Told me to look into investing in oil companies that were in the Bakken up in North Dakota. Which at the time not much going on. Thought whatever I'm 18 I need a new truck instead. Well 2006 they hit up there, I would have been a multimillionaire before I graduated college. Could have been retired essentially before age 30.

[BigRedChief]

I was in tech early. At the time I could have bought almost every website you have ever heard of or had value. Each domain, at the time, cost $75 to register the domain. Furniture.com, LA.com, Groceries, Taxes, broadband.com etc etc

I knew Google was going to win the search wars because their results were real and marked sponsorship placement. The others put sponsored results first.

I was is a mining Bitcoin with a group while I was still on a dial up modem. Only got about $8 total over 4 months so I gave my 11 Bitcoin to another dude.

I tried to convince the wife to grab these above but she said no, we cant gamble when we have no money. I couldnt even tell her that the .com was going to be the domain for business. It was about 60/40 at the time with .biz. We were piss poor at the time. So we'd have to spend $150 to cover one site to park.

Cant complain about my life I did get to lead. Where I ended up as a retiree. Yes, I still give her shit about saying no.