Skip To Content
    Posted on Dec 14, 2015

    29 Songs That Will Remind You Of Your High School Sweetheart

    You will always be my boo.

    by ,

    1. "Always Be My Baby" — Mariah Carey

    Columbia / Via youtube.com

    Probably listened to when: You were driving to the movies for a date.

    2. "My Boo" — Usher feat. Alicia Keys

    LaFace / Via youtube.com

    Probably listened to when: You were at the mall with your friends and exclaimed, loudly, "This is ____ and I's song!!!"

    3. "Like You" — Bow Wow feat. Ciara

    Columbia / Via youtube.com

    Probably listened to when: You were sitting in your parent's living room sneakily making out.

    4. "Stickwitu" — The Pussycat Dolls

    A&M / Via youtube.com

    Probably listened to when: You put it as your Myspace song after a fight.

    5. "Dilemma" — Nelly feat. Kelly Rowland

    Motown Records / Via youtube.com

    Probably listened to when: You were slow-dancing at a school dance.

    6. "The Reason" — Hoobastank

    Island Def Jam / Via youtube.com

    Probably listened to when: You were lying in your room and your boo had called and your parents said it was too late to talk.

    7. "All My Life" — K-Ci & JoJo

    Geffen Records / Via youtube.com

    Probably listened to when: You had just broken up and you were being a masochist.

    8. "We Belong Together" — Mariah Carey

    Def Jam Records / Via youtube.com

    Probably listened to when: You were grounded and your parents wouldn't let you see your boo so you laid in the dark listening to this for hours at a time.

    9. "Into You" — Fabolous feat. Tamia

    Universal / Via youtube.com

    Probably listened to when: You were driving around in a car with your friends and you wanted another excuse to talk about your boo.

    10. "Fall for You" — Secondhand Serenade

    Glassnote Records / Via youtube.com

    Probably listened to when: You stalked your ex on Myspace and found his new girlfriend and this was her profile song.

    11. "If I Ain't Got You" — Alicia Keys

    J Records / Via youtube.com

    Probably listened to when: You were on the bus to school, excited to see your boo, and you had actually remembered your CD player.

    12. "Crazy in Love" — Beyoncé feat. Jay Z

    Columbia / Via youtube.com

    Probably listened to when: You were making a mix CD for your car.

    13. "With You" — Jessica Simpson

    Columbia / Via youtube.com

    Probably listened to when: You downloaded it from LimeWire to play for your boo and gave your family computer a virus but blamed it on your sibling.

    14. "Everytime" — Britney Spears

    Jive Records / Via youtube.com

    Probably listened to when: You were watching MTV and saw the video and cried because, wake up, Britney, and you were in LOVE, duh.

    15. "Only One" — Yellowcard

    EMI Music / Via youtube.com

    Probably listened to when: You were on the bus to your track meet and had a lot of ~feelings~.

    16. "You and Me" — Lifehouse

    Geffen Records / Via youtube.com

    Probably listened to when: You were going on vacation with your family and wouldn't be able to see your boo for two weeks.

    17. "Baby Boy" — Beyoncé feat. Sean Paul

    Columbia / Via youtube.com

    Probably listened to when: You were trying out for the dance team and your crushed walked by.

    18. "All for You" — Janet Jackson

    Virgin / Via youtube.com

    Probably listened to when: You were dancing with your friends at the school dance but kept your eyes on your boo the whole time.

    19. "Wherever You Will Go" — The Calling

    RCA / Via youtube.com

    Probably listened to when: In between classes, writing the lyrics on a note for your boo.

    20. "Iris" — The Goo Goo Dolls

    Warner Bros. / Via youtube.com

    Probably listened to when: It came on the radio when you were in the car with your parents and you asked them to turn it up and they turned it up half a notch and you texted your boo complaining about it while using T-9.

    21. "On the Way Down" — Ryan Cabrera

    Atlantic Records / Via youtube.com

    Probably listened to when: You were on AIM trying to craft the perfect away message.

    22. "Lips of an Angel" — Hinder

    Universal Records / Via youtube.com

    Probably listened to when: You were having a lot of feelings and thought this song explained them even though it didn't at all.

    23. "Cupid's Chokehold" — Gym Class Heroes

    Fueled by Ramen / Via youtube.com

    Probably listened to when: You finally got your driver's license and your friend made you a mix CD and you were on your way to see your boo.

    24. "She Will Be Loved" — Maroon 5

    OctoScope Music / Via youtube.com

    Probably listened to when: It came on the radio in the car with your friends and you all rolled the windows down to sing at the top of your lungs and all you could think about was your love.

    25. "Rock Wit U (Awww Baby)" — Ashanti

    M.I. Records / Via youtube.com

    Probably listened to when: You were walking around the mall holding hands and it was playing overhead.

    26. "I Will Follow You into the Dark" — Death Cab for Cutie

    KROQ / Via youtube.com

    Probably listened to when: You had been together for three months and were thinking about your inevitable future together.

    27. "Burn" — Usher

    Arista Records / Via youtube.com

    Probably listened to when: You were together for one month and kinda already wanted to move on.

    28. "My Love" — Justin Timberlake feat. T.I.

    Jive Records / Via youtube.com

    Probably listened to when: You made a mix CD for your boo.

    29. "Everytime We Touch" — Cascada

    Robbins / Via youtube.com

    Probably listened to when: You were having a dance party alone in your room after a shower getting ready for a date with your boo.

    Now, while you stalk them on Facebook to see what they're up to, you have the perfect playlist:

    Nostalgia Trip

    Take a trip down memory lane that’ll make you feel nostalgia AF

    Newsletter signup form