People Break Down Their Biggest Regret From High School

People Break Down Their Biggest Regret From High School
Photo by kyo azuma on Unsplash

I don't miss high school or the people in it. People who seem to have peaked in high school also weird me out. How? Why? I can definitely tell you that life got much more interesting the older I got (my 20s were way more fun than any of my time in high school). If you were to ask me if I have any regrets, I suppose I would say that I wish I had been more assertive and stood up for myself more. Depression has a way of complicating goals like that, though. Let me tell you: It feels nice to be so much healthier than I was then.

After Redditor Sub2735 asked the online community, "What's your biggest regret from high school?" people shared their stories.

"I'm sure the mentality..."

Being too shy, I'm sure the mentality that everyone hated me wasn't very good for making friends.


"I'm not sure how it could have gone differently..."

Dropping out. I am not sure how it could have gone differently, but I do wish it had. It was expensive to upgrade all that education to get into post-secondary, and I also missed out on a lot of social things.


"I was already pretty cynical..."

I was told I had received a full-ride scholarship, so I stopped putting in any effort on other scholarships. When the time came, it wound up being awarded to someone who applied late, got it due to their family's income level, and then dropped out of college after one month. My first two years of college were a financial nightmare as I had to pay my own way on everything (except rent, as I lived at home and commuted across state lines for work and college). If I had $50 at the end of the month, that was a damn good month. I couldn't get student loans and my parents refused to help, so I had worked out a deal with the financial office at college to pay something like $550 a month, which was about 90% of my income.

I regret not confronting whoever made that decision about the scholarship. I somewhat regret not putting in the effort to get other scholarships at the same time, but I can't blame myself for it either.

I was already pretty cynical at that point, but that was when I realized just how quickly your back becomes a knife block for someone else's optics.


"I used to daydream..."

I used to daydream about going back one day and burning it to the ground, but it's just been demolished by land developers. So I guess that dream's dead.


I suppose the phrase, "Always follow your dreams"...

...doesn't apply in this case.

"I've never met anyone..."

My best friend asked me out on a date once. I said no because I didn't didn't want to risk our friendship. We remained very, very close for years after we graduated and went our separate ways but time and distance eventually did what they do. I've never met anyone who understood me so well before or since, and the thought of what might have been keeps me up at night.


"Not accepting I was bi sooner..."

Not accepting I was bi sooner and not telling a gay guy who obviously had a crush on me I felt the same way.


"Acting like a clown..."

Acting like a clown, annoying everyone to the point where no one really stayed in contact with me after, and taking my precious little charter school for granted.


Hindsight is 20/20.

Don't be so hard on yourself, whoever you are. High school years are difficult times for almost everyone.

"By the time I graduated..."

Wasted the majority of my high school years chasing girls and unrealistic desires. By the time I graduated, I realized I was so caught up in my thoughts that I didn't see what was going on around me and I missed out on a lot of important opportunities. Don't let important times slip past you for temporary happiness.


I have a friend who has expressed similar concerns about his time in high school.

He ended up spending his college years going to therapy and maturing. His clownish antics were a coping mechanism for a lot of crap going on in his life at the time. He's happier and healthier now and that's what matters.

"To be fair..."

Dating my best friend. To be fair that's how I found out a lot of people weren't really my friends but getting ghosted afterward really hurt.



Ghosting is so immature.

"She got tired..."

I took my crush to Daft Punk Alive 2007 instead of my best friend. She wasn't responding all day, and I was with my friend. We were about to leave when she called. She'd been with her boyfriend all day and had forgotten about the concert. I took her. My buddy was disappointed but cool about it.

She got tired of being on the floor halfway through so we sat in the bleachers. We started walking out before the encore because she wanted to get home sooner.

Always wanted to take my buddy to a Daft Punk show after that, and was going to, no matter where or how much it cost. But I'll never get the chance.


"Oh well."

Realizing my nerdy @ss could have been with someone way out of my league. Oh well. Things worked out in the end.


"Looking back now..."

I regret not telling my crushes how I felt about them. Looking back now, I know that those puppy love relationships probably wouldn't have developed into anything long term and I no doubt would've had my heart broken when they inevitably ended but, I can't help but wonder: What if?

Having cultivated a host of insecurities by the time I got to high school, I was really good at hiding my inner thoughts and feelings - I also probably didn't see myself very clearly. So, I just assumed that there was zero chance of my crushes reciprocating my feelings and never said anything to them about it. I also probably sub-consciously ignored any signs that they were interested in me (again, didn't see myself clearly, was very insecure).


"The world is wider..."

Not engaging with opportunities available to me and just looking at it like a holding pen just before adulthood.

It may seem hokey, but join clubs, try out lots of sports, pursue interests, pay attention in class and engage with your peers.

The world is wider for adolescents than I allowed myself to believe it was at the time.


"I already knew I was quitting..."

Senior year I had the option of a guaranteed internship and doing half days at school. Turned it down because my parents wanted me to be in band (and I enjoyed it so didn't put up a fight).

I already knew I was quitting when I went to college. The internship would have been great experience to propel my studies/career.


High school isn't easy.

Nor is it particularly fun for a lot of people. Remember how awful being a teenager was? Remember what it was like to feel like you were at the whim of your hormones all the time? It's an emotional rollercoaster. It's no wonder so many people would rather close the book on high school once it's over (or have some regrets related to their time there).

Have your own stories? Feel free to share them in the comments below.

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