I wanna date you, go steady and wear your letter pin
Or your letterman sweater like Ola Ray but I'm hesitant

from Jean Grae – Away With Me Lyrics on Rap Genius

Ola Ray is an American model who starred in the Michael Jackson video, Thriller. This man makes Jean want to be old fashioned and ask him to go steady by pinning him.

To “pin,” “get pinned” or “be pinned” is a U.S. tradition that occurs when a college man gives his girlfriend a pin as a symbol of their “going steady” or commitment to one another.

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