Lyric discussion by JesseBaker 

I never saw the song to be about a promiscuous girl so much as a girl who her classmates/friends all gossip about as far as guys claiming to have slept with her. The middle section (the one who insists he was first in the line/is the last to remember her name) makes me think of the "Caroline" character being sung about being someone who wasn't easy but all of the guys say they slept with her, are really the guys who shunned her and not bothering to remember her name if told. "Pretty In Pink" could be seen as sort of a code of sorts; an attractive but upopular girl who is a bit of a dreamer, wanting to fit in with her peers and is always seen wearing pink, which becomes how her peers think of her (IE the hot looking girl who is always wearing pink that they can't be bothered to remember her name yet brag about having sex with her in private).

The final part is the narrator of the song being with Caroline; perhaps being a guy who likes her and who knows who she is and is in a relationship with her. They have sex (these cars collide) and the rest of the third part of the song is about how Caroline is madly in love with the narrator and the implications of her being a virgin despite the gossip of her being a slut. "She doesn't have anything You want to steal, Well Nothing you can touch"= refers to her giving her virginity up to her narrator boyfriend; "Caroline talks to you Softly sometimes She says 'I love you' and 'Too much'" refers to her love for the narrator; loving him enough to give up her virginity.

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