Okay so I haven't fully loved all (or most) of these guys but it made for a great and dramatic list title (CLICKBAIT!!!!!) These men are of varying importance, but if there's a song I still can't listen to without thinking of them, they made the list. In chronological order.
  1. "Stickwitu" - The Pussycat Dolls
    UGH I was in love with my best friend's twin brother for literally years and he asked me to Winterball and we slow danced to this song!!! It never worked out but we stayed really close and then he hit on me when we were 23 and I felt fucking vindicated
  2. "Okay I Believe You But My Tommy Gun Don't" - Brand New
    Okay so this was the first boy I ever truly pined for. He drove me to school one morning (yes I still remember the date but I'm not going to tell you that) and this was the song on the radio. We went on a single date (and to prom!!!!!!!!!) but it never worked out despite my best efforts.
  3. "Nightswimming" - REM
    Ugh this one goes out to that guy I met at church camp. We all have a guy we met at church camp, amirite? (Please say yes)
  4. "I'm Yours" - Jason Mraz
    UGH MY FIRST "LOVE"!!!! I heard this song for the first time in March '08, a solid three or four months before it entered the national consciousness, and presented it to my high school boyfriend as "our song". That always made me feel like we had a leg up on the other couples who thought it was their song (IT WASN'T, IT WAS OURS DAMMIT). Actually just listened to this song for the first time in probably 7 years the other day and got supes nostalgic.
  5. "Without You" - A pan flute instrumental, in the style of Mariah Carey
    This was playing during a particularly terrible first date at a Chinese restaurant. We ended up going out on a LOT of dates but it all ended when he asked some other girl to prom like a fucking dweeb.
  6. "Ashamed" - Deer Tick
    A boy I had a crush on sent me this song to listen to and I thought he was just being nice to indulging me in convo because omg who would ever like me???? Then 6 months later, he drunkenly admitted that he was flirting with me and by then it was TOO LATE. The One Who Got Away
  7. "Runaround" - Blues Traveler
    The boy I was dating was super into Blues Traveler so I tried to be into Blues Traveler, a band I will never understand. This is from a period of my life before I realized that boys would still like me even if I wasn't the #1 fan of the things they like
  8. "I'll Be There for You" - Bon Jovi
    My first Serious Boyfriend™ and I used to scream sing this in the car together. He was the first guy I was ever super goofy with and it made me realize I didn't have to be a chill gurl.
  9. "Blue Eyes" - Cary Brothers
    A boy I only kind of liked played this song for me and told me it reminded him of me because of my "beautiful blue eyes". Then I reminded him that my eyes are actually green and it got weird.