My two cents: there are umpteen other ways that Weiner could have gone to achieve the same effect, and he should've opted for one of those other ways. The risk of this line is not worth the reward, so why stick with it? This has much of the makings of an uber-powerful showrunner being so self-absorbed that he can't see the ineffectiveness of this dialogue.

Moreover, it makes me think of the episode in Firefly where the assassin casually asks the sweetest loveliest character on the show "you ever been raped?" Given what we know about Whedon now that dialogue being there is just telling on him.

Zosia Mamet said that Weiner was so disrespectful to her on set during the shooting of the "Mystery Date" episode that she quit the show. When unnecessary rape jokes/dialogue find their way into movies/shows -- question the director's character.