Submitted to: Contest #306

Penelope's Diary

Written in response to: "Tell a story using a series of diary or journal entries."

High School Sad Teens & Young Adult

This story contains sensitive content

Penelope’s Diary

*This story contains sensitive themes including: hints of suicidal intentions, substance abuse, and deteriorating mental health*

September 3rd, 2023.

Dear diary,

Today’s my first day of senior year and I promised to document my journey, no matter how cringey it seems as I write. While high school has been a little rough- okay a lot rough, I am excited to finally enter my last chapter here and I really hope this year is different.

I admit that I have never actually tried to ‘fit in’ or whatever, but it’s our last time being in the same place that must count for something…right?

Okay I am getting ahead of myself, firstly I need to think of everything I wish to accomplish by the end of this year:

Maintain my perfect GPA (obviously).

Have fun with my friends.

Try to be okay.

I have a good feeling about this year so who knows, maybe I will finally get that ‘high school experience’ everyone gushes about :)

Till tomorrow, Penelope <3

September 17th, 2023.

Dear diary,

I know I promised to update you every single day, but honestly, I don’t have that kind of time, so let me just summarize what has been happening.

So far, school’s been going academically well, my electives are fun, and I am learning new things, however, it seems that I have caught the ‘attention’ of one of the popular troublemakers in my class and I can’t scare him off, his name is Dean.

I am well aware that this is a form of bullying/mocking, I am not stupid, but it is kind of nice to get attention even if it’s not what I should hope for.

Anyhow, I still haven’t really had any major fun, but Halloween is right around the corner so maybe I will go to a party or something?

Manifesting good thoughts, Penelope.

October 14th, 2023.

My dearest diary,

I HAVE MAJOR UPDATES!!! Dean and I have been getting closer, and I think underneath all that sarcasm he’s actually kind of sweet and funny, but anyway, he just asked me today if I wanted to go to a Halloween party with him, in matching costumes!

I have been bursting with excitement and nerves since he asked, and I don’t even know what to wear or if I should just go out and not do my work early; being an actual teenager is such a mess.

My friends are pretty happy for me, except Kenzie who’s being so annoying and keeps telling me to be careful around guys like Dean, ugh she’s probably jealous or something.

I will tell you all the details after Halloween, Penny :) (it’s a new nickname Dean’s been calling me and it’s so cute).

October 31st, 2023.

DEAR DIARYYYYY,

I AM SO OMG I CAN’T EVEN WRITE I AM BUZZING WITH ENERGY.

DEAN.KISSED.ME

I KNOW IT’S UNBEALIVABLE, BUT I HAD MY FIRST KISS TONIGHT AND WE ARE NOW OFFICIALLY DATING AAAAAAAA.

WE WERE SO CUTE DRESSED AS MEG AND HERCULES AND HE EVEN HELPED ME TRY WEED FOR THE FIRST TIME.

UGH BUT STUPID KENZIE GOT ME HOME AND TOLD ME I SHOULD BE ‘CAREFUL,’ LIKE WHAT IS HER DEAL, I AM HAVING FUNN FOR THE FIRST TIME EVER.

I GOTTO GO NAP BYEE, PENNYBOO.

November 22nd, 2023.

Dear diary,

I don’t think I knew happiness and fun till I met Dean; like seriously, I used to be a joyless nerd and now I am a teenage girl who lets loose and has fun, occasionally high and kissing her gorgeous boyfriend.

Are my grades slipping a bit? Maybee, but I am still in the top students so what’s the harm in being free and going out every weekend.

I may not be friends with Kenzie and my other friends anymore, but they were being so bitchy about how I am ‘ruining my life for some temporary fun,’ like can’t a girl just be left to her devices God!

Anyway, I am going out with my boo, see you soon queen, love Penny <3.

December 31st, 2023.

Diary,

I am rushing through this because I need to tell someone, or I will combust.

Dean and I went all the way today and I think I regret it.

Obviously, I love Dean, but he’s been hounding me for two months now, so I just gave in…why do I feel empty?

It’s probably nothing and we will be okay, Penny.

January 8th, 2024.

Dear diary,

It has been over a week now and Dean hasn’t even talked to me and especially about what we did.

Did I make a mistake? Was it too soon? God, I don’t even know.

The weed has been helping, but I think it’s not strong enough…teens experiment with other drugs, right?

Don’t even worry, I am not a junkie, I know my limits, Penny.

February 5th, 2024.

Dear diary,

Dean broke up with me.

He said it’s not me, but why do I feel like he’s lying?

It hurts to breathe or talk or even function, so I am trying molly.

Kenzie says I am not too far gone, that she could help, but I snapped at her, I don’t even know why I did that.

I just want to be okay again, he made me feel okay.

Maybe the pain will never stop, Penelope.

March 19th, 2024.

DIARY,

OH MY GOSH I AM FLOATING IT’S AWESOME.

I SAW DEAN KISSING ANOTHER GIRL, BUT I DIDN’T CRY WOOOO.

MARCUS FOUND ME AND GAVE ME…SOMETHING, BUT IT’S SO COOL

I AM NOT CRYING ANYMORE, PEN (THAT’S WHAT MARCUS CALLS ME)

April 1st, 2024.

Dear diary,

I am not an addict.

Everyone is being so fucking dramatic, and I am over it.

My mom keeps crying because that bitch Kenzie snitched that I am doing a little ecstasy like wow, can she get a freaking life.

I can fucking quit if I want to, but until Dean leaves that ‘thing’ he probably left me for I am not going to.

I don’t have a problem, Marcus said so and he’s the only one still here, Penn.

May 31st, 2024.

Dear diary,

It’s graduation day and I don’t have a GPA anymore, I think.

I don’t have a boyfriend.

I don’t have any friends.

I just have my pills, who love me.

I can’t even walk on stage because I am an ‘addict.’

Old Penelope would weep if she saw me and she was right.

Maybe there truly is nothing left for me, even Marcus said the minute I touched heroin I am a goner.

So, I guess this is goodbye? Maybe? Penelope.

June 1st, 2024.

………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………..

THE END

Posted Jun 14, 2025
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