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6 Songs That Take Me Back to My Middle School Years | Moonlight Sweetness

6 Songs That Take Me Back to My Middle School Years | The Nostalgia Diaries Blog

Even though school may be out for summer, that doesn’t mean we still can’t be nostalgic for our own (old) school days! And today’s reader-submitted nostalgic playlist, 6 Songs That Take Me Back to My Middle School Years by Andrea at Moonlight Sweetness, is sure to make you nostalgic for those fun, exciting, and—admittedly—sometimes painful middle school years.

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6 Songs That Take Me Back to My Middle School Years | Moonlight Sweetness

I actually liked my middle school years, you know? Sure, there was drama and crying (lots of tears) and the occasional “I hate everybody” stuff, but all in all, those years were good and fun. I can’t complain. Here are my favorite 6 songs from this episode of my life that always get me all nostalgic. 

I would literally sing this song to the top of my lungs. Especially the parts where it says “and I don’t want the world to see me, cuz I don’t think that they’d understand” and “when everything feels like the movies, yeah you bleed just to know you’re alive”. I was going through so many changes back then but this song, nostalgic as it is, made me smile. And it was just that: I felt so misunderstood back in those days and these song made me feel like someone was actually understanding me. 

To this day, it still remains my heartbreak song. I don’t know why, but EVERY SINGLE time a boy or my crush did something mean to me, this is the song that played on the radio. Or, I would listen to the song and a few hours later, *boom!*, a heartbreak came along. 

Awww… the “romantic-ness” in this song. This is one of the songs I always longed to be dedicated to me, but nope, no guy ever dedicated this song. This song always reminded me of my crush, or if I didn’t have one, it was like “Hey, hun, time to find some boy you’re into, okay?” 🙂

Every time I hear this song, flashes of Ryan Phillipe and Reese Witherspoon go through my head. And as I hear this song, my mind wanders and starts imagining I’m in a classic convertible, wind blowing my hair, cool shades on and listening this really loud while cruising some British road (nope, I’m not British, not even close). Yeah, me and my imagination. 

This is the song I thought would be playing for my first kiss. I would sing it vigorously. What this song describes is what I thought my first kiss would be like, but hey, turns out it was way better! Ha!

This song reminds me of all the mean things my crush did (his friends included). It was—and still is considered—really mean to make me believe he was really into me. He would yell it in front of his friends and all that, but it was just to put up a show. The next day, he peacocked in front of the whole school with his new girlfriend. Yikes!


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I think you can tell the “dramas” that happened during my middle school years by hearing these songs. As I was writing this, I laughed so hard and said to myself “what were you thinking?” If you couldn’t tell, things kinda revolved around “crushes” of mine. 🙂

moonlight-sweetnessAndrea, a 29-year-old coffee enthusiast, is the awesome blogger over at Moonlight Sweetness. Along with being an event planner, a translator, and transcriptionist, she also loves to travel, eat delicious desserts, and drink good wine. She’s also the creator of her own coffee, Gardenia de Plata.

You can follow Andrea online here:
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Thank you, Andrea!
Now it’s your turn: What songs take you back to your middle school years?

Want to submit your own song or playlist to be featured on a Music Monday post? Email us today! We can’t wait to hear your own nostalgia-inducing tunes.


At The Nostalgia Diaries, our goal is to help you simplify, enhance, and engage your lives by focusing on the most important things: remembering, appreciating, believing, and becoming. It’s all about celebrating the past to create better days today.


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24 thoughts on “6 Songs That Take Me Back to My Middle School Years | Moonlight Sweetness

  1. Thanks so much for letting me contribute! I had so much fun writing this list and remembering my filled-with-drama middle school years 🙈😂 You made my day! Cheers! 🙂

  2. I love reading what you will blog about next. This is a great list and took me down memory lane! Iris though…. one of my faves

  3. Middle school was not a great time for me haha. I think in Middle School we were listening to NSYNC, Britney Spears, and Christina Aguliera. I remember slow dancing at a middle school dance to “I Turn to You” by Christina haha.

  4. Love this! For me, it was all about “chicago” (the band). Too many fun memories!

  5. This is college years for me, but Bittersweet Symphony is still one of my all-time favorite songs!

  6. Oh wow. This is a great playlist! I remember all of these songs! I used to sing “This Kiss” all the time when it was on the radio and I distinctly remember watching the Torn music video on TLC with Carson Daly! Such flashbacks!

  7. Some of these are a little before my time, but I definitely remember most of these! Such a good list! 🙂 I would add that my list is a little more of the early 2000’s such as Hilary Duff, little bit of Smashmouth and other randoms lol

  8. #3 – my all-time favorite song ever!! Also #5 – I’m a huge Faith fan! Can’t believe she’s in her 50’s…I grew up with her music.

  9. Oh gosh this is so embarrassing but definitely all things “alternative” at the time like Boys Like Girls (Thunder), We The Kings (Check Yes Juliet), etc., haha! Loved this post as it took me back to my middle school days.

  10. I totally remember these too (I’m 31). I remember the days of boy bands and girl singers like Britney and Christina, as well the pop-punk boy bands. Also, the days of TRL and Carson Daly (I’m so bummed that I never got to be in the audience hahah)

  11. My Middle School years were not my best – but come to think of it, I did make some lifelong friends during that time. Your post makes me feel so old, as I was in Middle School in the mid-80’s! Stray Cats, Quiet Riot and a young Madonna come to mind.

  12. Anything from the Dirty Dancing soundtrack, Debbie Gibson, Tiffany, Madonna, Rick Astley…. All take me back to 8th grade 🙂 Typing this out I suddenly feel old LOL!

  13. I am not sure what middle school is as we don’t have it in Australia.. But I am guessing it’s around grade 8-10? All those songs above take me back to my high school days. Bittersweet Symphony still gets good rotation even now. Just hearing the opening string instruments gives me chills.

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