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My Five Biggest Regrets

Nostalgia can be a curse and to prove it I’ve created a list of five times in my life that I made a decision I’ve always slightly regretted. I’m calling it ‘My Five Biggest Regrets’ but the title is a bit misleading. Creating a list like this is a really important thing to do and if you’re going to get it right then you have to be constructive and try to determine whether in all probability you’re either right or wrong in each case. What do YOU regret? It’s a killer question. If the Road to Hell is paved with good intentions, then I strongly suspect that the Path to Dissatisfaction is paved with overly nostalgic memories, especially ones involving missed opportunities. If you’re autistic, an overthinker or even just an unusually reflective person, then the retrospective analysis is probably a huge part of your mental landscape. In simple terms, retrospective analysis is where you overplay conversations in your head after the event, often applying your own biased narrative to anything that was said. What you end up coming out with can potentially do catastrophic damage to friendships and relationships or even destroy them completely. It’s a curse of a burden to bear, which is why I find movies like ’13 Going on 30′ so incredibly difficult to watch.

For those of you who aren’t familiar with the movie, ‘13 Going on 30‘ is a film about a young girl in the 80s (my own childhood era) who fervently desires adulthood and regularly wishes away her life until one day – thanks to some literally magical stardust – she wakes up to find herself an adult whose life is built almost entirely from every bad decision she has made since the fateful 13th Birthday Party when the magic happened. To be clear, she spends a lot of time – aged 13 – ignoring the best friend who quite clearly adores her in favour of winning the approval of a truly odious bunch of stereotypical mean girls who end up becoming her adult friends on the unfortunate life path she ends up pursuing. Typical Hollywood mayhem ensues, though this is actually an incredibly emotional film with a very deep and powerful message disguised as a fairly standard romcom.

Watching this movie with my daughter got me thinking about the things I most regret and whether or not on second thought I genuinely think that – with hindsight – they were actually bad decisions. Here’s the list I came up with: take a deep breath because some of them might seem genuinely insane until they’re explained.


Going back to School after a dental appointment when I was eight. This one sounds incredible…but it was my first regret and it’s tied to something much bigger. My mum dropped me back at school after taking me to a pretty traumatic dental appointment but at the last minute she asked me if I wanted to go home instead: I said ‘no’ and went back to school. That afternoon, I had my first vasovagal attack and suffered arguably the most embarrassing incident in the entirety of my childhood: cutting myself, passing out on the floor of the playground, going deaf and blind and wetting myself in front of half the school. I know enough now about myocardial syncope to understand that it could have happened at any time…but it nevertheless felt like I was being punished for making the wrong choice. IN RETROSPECT: This could have happened at any moment during my childhood; only the timing was unfortunate.


Asking out the girl I fancied in the last year of primary school. This seems like quite a small and common regret in comparison to many on the list but for me – a kid who suffered (as I still do) from ‘All or Nothing Thinking’ – the rejection wasn’t simply a rejection from her, it was a rejection from ALL girls. I wouldn’t ask out anyone else for more than a decade and the situation completely destroyed my confidence. The script in my head changed from ‘There’s Always a Chance’ to ‘All Girls Hate You’ and that was that. IN RETROSPECT: I actually still think that this was a bad idea and I STILL regret it: if I’d waited until secondary school then I’d have seen enough rejection around me to simply feel like part of the pack.


The Dungeons and Dragons Hut: I use this description as a sort of umbrella term for a series of situations in secondary school where I chose things like fantasy roleplaying games and other daydreaming hobbies instead of focusing on proper friendships and relationships. I do remember one particularly poignant moment where I had a choice of following the ‘normal’ (hate that word) kids into the canteen or going with my ‘own kind’ and heading with the geek group to play a few fantasy adventure games. I’ve always wondered if I would have been happier pretending to be somebody I wasn’t as I’ve never really felt at home among any social group so I might as well have played both sides of school instead of the nerdy group I formed a sort of self-imposed exile with. IN RETROSPECT: this is such a tough one – although I hate to be a traitor to my tribe, I spent so much time with my head in the clouds that I never really experienced life. The whole fantasy world in my head ended up exploding outwards, making me a fortune and enabling me to live mortgage-free at 24…but it also robbed me of so much LIFE in the process. The balance isn’t always easy to reconcile but on average I feel like the price of success was simply too high.


So many of my regrets involve friendships and relationships but if I could go back to my days at Blockbuster Video (arguably my most formative job) then I would hang out with the guys more away from the store, party with them a lot more than I did and ask out the girl I fancied without being hugely constrained by always doing the right/smart thing and not the thing that would lead to the least trouble. I’d drink more and probably experiment more with a less straight edge lifestyle. IN RETROSPECT: This one is, I guess, a lot easier to argue. If I’d dated the girls I fancied back then there’s a good chance I wouldn’t have married the woman who is undoubtedly my soul-mate and had two beautiful children. If I’d partied and hit the bottle more, there’s a strong chance my career wouldn’t have exploded in the way that it did.


In 2016, following a family death and something I now recognise as a breakdown, I settled into a period of hugely destructive behaviour which ruined one of my wife’s closest business relationships and destroyed at least three of her friendships. In this situation, I was out of control and entirely to blame: I wasn’t myself but really couldn’t see that at the time. The results were hugely chaotic. IN RETROSPECT: This one is a no-brainer. If I could go back, I wouldn’t have the two or three conversations that brought a lot of emotion to the surface. I know it’s not great to bottle up emotions…but in the case above I simply should have swallowed all the feelings and ideas that were swimming around in my head and used them to identify that I was in quite alarming amounts of pain and suffering with grief. Sometimes, we don’t really understand that we’re drowning until we make it out of the water and onto the shore.

‘What Do YOU Regret?’ was written by Davey Stone on Wednesday 7th April, 2021. If you enjoyed ‘What Do YOU Regret?’ please consider following the blog.

The post My Five Biggest Regrets appeared first on Bloke Called Dave.

This post first appeared on David Grimstone: Books, Biogs, Audio, please read the originial post: here

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My Five Biggest Regrets


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