Found this one through Cracked.com’s “Letterman’s 9 Most Hilariously Awkward Interviews.”
In residency, I had a fan. I took care of her after a car accident and after that she became my senior year project. She was cute and zaftig and she always dressed to the nines, and she was one of those rare women who (A) seemed to have a crush on me and (B) still had all of her teeth. If ever I could have had an affair, she was it. I remember being so flattered by the whole thing that it never occurred to me that I might be hurting her feelings by NOT coming on to her. But hey, that’s not me. One of my classmates — no, wait, TWO of my classmates — would have jumped her in an instant. But not me.
Anyway. One day, she brought in Madonna’s book so that she could show me the black and white photo of the guy with the airbrushed asshole. Maybe this was her way to share a laugh with me (because it was pretty damn funny, that picture) or maybe it was her awkward way of making one last attempt. So we looked at that photo and the other photos and laughed about it, and that was all. I don’t think she ever came back to my clinic.
That’s my Madonna story.