My Middle School Diary Excerpts That Help Explain Why I’m Still Single

Rachel Marsh
5 min readAug 8, 2022

Like all angsty pre-teens, I kept a diary. This diary mostly just contained my feelings about the boys I liked, all of whom I was way too afraid to ask out, talk to, or even make eye contact with.

But even though I was too awkward to interact with anyone that I did have a crush on (take, for example, the incident where I went on a date with the boy I liked and didn’t speak to him the entire time), I held my standards extremely high.

And now, in reading through my middle school diary as an adult, it makes more sense why I’m 34 years old and the level of single where you read Craigslist Missed Connections every night “just in case.”

This first incident took place in my sixth grade social studies class. Halfway through the year, a new kid named Doug joined the class and was seated right in front of me.

Doug used to turn around and flirt with me during class, which was fine but I wasn’t remotely attracted to him. He had weird teeth and the kind of boy bangs that are supposed to be spiked up with gel at that time in the year 2000, but he apparently wasn’t aware or didn’t know how to so they just laid flat and fuzzy on his forehead.


Oh my GRACIOUS! I’ve almost been asked out! Seriously! Okay, see, this guy Doug, he sits in front of me in social studies class and right before the bell rang, he said, “I need to talk to you after class.” And I totally swear, my insides just went majorly cold. Because I totally suspected he liked me.

You see, it’s not like I really like him or anything. In fact, I don’t even think he’s at all cute. I mean, I guess he’s okay for a friend, but not, I repeat NOT for a boyfriend.

But anyway. I just said, “Well, I can’t, cuz I gotta go fast.” And he’s like, “What?” And I just said, “Nevermind,” and went to my locker hoping he would not follow, which he didn’t.

I could have dated someone very nice back in sixth grade, the kind of boy who wasn’t popular but who had very soft hands and a stable family; but instead, I came up with an infallible excuse to avoid getting asked out for the first time in my life.