Life Biggest Regret(s) of Your Life - Page 7

GabyKeepsMeWarm · 04-18-2025, 02:51 AM

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?

BWillie · 04-20-2025, 12:33 PM

I almost thought about settling down with a smoke show before I moved to KC from Iowa City. It was either get serious and move in with her in Bettendorf Iowa or move to KC and party for a while.

Sure glad I chose the latter. I could be working at a fkn bank, going to kids ball games in Eastern Iowa with the highlight of my week eating a funnel cake on Sundays. Thank god I chose wisely. That would have been awful.

Now I have a girl that lets me be me for the most part.

PunkinDrublic · 04-20-2025, 04:03 PM

Antifreeze, not all advice given on CP is a good idea.

stumppy · 04-20-2025, 04:28 PM

Quote:

Originally Posted by BWillie

I almost thought about settling down with a smoke show before I moved to KC from Iowa City. It was either get serious and move in with her in Bettendorf Iowa or move to KC and party for a while.

Sure glad I chose the latter. I could be working at a fkn bank, going to kids ball games in Eastern Iowa with the highlight of my week eating a funnel cake on Sundays. Thank god I chose wisely. That would have been awful.

Now I have a girl that lets me be me for the most part.

I'd give anything to be able to do all that stuff all over again. Raising my children was the highlight of my life. Second best is the grandchildren I have now.

George Liquor · 04-20-2025, 04:40 PM

Quote:

Originally Posted by stumppy

I'd give anything to be able to do all that stuff all over again. Raising my children was the highlight of my life. Second best is the grandchildren I have now.

Having kids is the best thing I've ever done. Sure, I miss being a degenerate sometimes. But I wouldn't trade anything for them.

(Even though they can be exhausting)

Pepe Silvia · 04-20-2025, 04:41 PM

Quote:

Originally Posted by BWillie

I almost thought about settling down with a smoke show before I moved to KC from Iowa City. It was either get serious and move in with her in Bettendorf Iowa or move to KC and party for a while.

Sure glad I chose the latter. I could be working at a fkn bank, going to kids ball games in Eastern Iowa with the highlight of my week eating a funnel cake on Sundays. Thank god I chose wisely. That would have been awful.

Now I have a girl that lets me be me for the most part.

At least funnel cakes are awesome.

**007** · 04-20-2025, 05:27 PM

Having disk replacement surgery. I'm worse now than before. Should have never done it.

BWillie · 04-20-2025, 05:47 PM

Quote:

Originally Posted by Pepe Silvia

At least funnel cakes are awesome.

I left my kid at the mall when he was 3. He was looking at a cat. Best decision Baby Billy ever made.

**ShortRoundChief** · 04-20-2025, 06:10 PM

Quote:

Originally Posted by 007

Having disk replacement surgery. I'm worse now than before. Should have never done it.

They’ve been trying to get me to do that for years and I always say no. A couple of times I even had it scheduled but canceled. Thanks for sharing your experience as that’s my biggest concern facing it.

**007** · 04-20-2025, 06:17 PM

Quote:

Originally Posted by ShortRoundChief

They’ve been trying to get me to do that for years and I always say no. A couple of times I even had it scheduled but canceled. Thanks for sharing your experience as that’s my biggest concern facing it.

I'd give anything to go back and undo that decision. Meanwhile I'm paying the bill for the next three years on a surgery that made things worse.

**Iowanian** · 04-20-2025, 07:14 PM

Your regrets change with perspective of life.

Things I regretted 5 years ago might not be on my radar today.

GabyKeepsMeWarm · 04-20-2025, 07:35 PM

Quote:

Originally Posted by Iowanian

Your regrets change with perspective of life.

Things I regretted 5 years ago might not be on my radar today.

Absolutely.

And I’m not looking to go back in time. Things for me are really pretty good, and I’ve got limited complaints.

But we’ve all got regrets. Even if taking a step in one road meant walking away from the other road, we’re all curious about those moments. But this thread isn’t about taking a different road. It’s about making decisions, being accountable and looking back with regret.

Good for some of you who have no regrets.

Pepe Silvia · 04-20-2025, 07:37 PM

Quote:

Originally Posted by BWillie

I left my kid at the mall when he was 3. He was looking at a cat. Best decision Baby Billy ever made.

And gave him a genuine pair of Oakley's.

Katipan · 04-20-2025, 08:20 PM

Quote:

Originally Posted by GabyKeepsMeWarm

Absolutely.

And I’m not looking to go back in time. Things for me are really pretty good, and I’ve got limited complaints.

But we’ve all got regrets. Even if taking a step in one road meant walking away from the other road, we’re all curious about those moments. But this thread isn’t about taking a different road. It’s about making decisions, being accountable and looking back with regret.

Good for some of you who have no regrets.

Maybe you should have stated the rules at the beginning before trying to have a conversation.

**Rain Man** · 04-20-2025, 08:30 PM

Quote:

Originally Posted by Katipan

Maybe you should have stated the rules at the beginning before trying to have a conversation.

Do you think he regrets that?

teedubya · 04-20-2025, 08:32 PM

Spending too much money on weed and not enough on Amazon & Apple in the mid 90s.

04-18-2025, 02:51 AM
GabyKeepsMeWarm I'll **** anything that moves! Join Date: Jan 2022 Casino cash: $-2060000	Biggest Regret(s) of Your Life 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?
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04-20-2025, 12:33 PM	#91
BWillie Are you ready to Rumble? Join Date: Apr 2006 Casino cash: $-1188759	I almost thought about settling down with a smoke show before I moved to KC from Iowa City. It was either get serious and move in with her in Bettendorf Iowa or move to KC and party for a while. Sure glad I chose the latter. I could be working at a fkn bank, going to kids ball games in Eastern Iowa with the highlight of my week eating a funnel cake on Sundays. Thank god I chose wisely. That would have been awful. Now I have a girl that lets me be me for the most part.
Posts: 52,246

04-20-2025, 04:03 PM	#92
PunkinDrublic Stay down bitch! Join Date: Jun 2001 Location: Plano, TX Casino cash: $4500670	Antifreeze, not all advice given on CP is a good idea. __________________ Disappointing my parents since 1976
Posts: 9,539	1 0

04-20-2025, 05:27 PM	#96
007 Shaken. Not stirred. Join Date: Sep 2002 Location: London Casino cash: $12250126 VARSITY	Having disk replacement surgery. I'm worse now than before. Should have never done it. __________________ My dear girl, there are some things that just aren’t done. Such as, drinking Dom Perignon ’53 above the temperature of 38 degrees Fahrenheit. That’s just as bad as listening to the Beatles without earmuffs.
Posts: 65,732

04-20-2025, 07:14 PM	#100
Iowanian Supporter Join Date: Aug 2000 Location: Utopia Casino cash: $1868454	Your regrets change with perspective of life. Things I regretted 5 years ago might not be on my radar today.
Posts: 62,921

04-20-2025, 08:32 PM	#105
teedubya Most Valuable Poster Join Date: Oct 2003 Casino cash: $9023042	Spending too much money on weed and not enough on Amazon & Apple in the mid 90s.
Posts: 36,825	3 0