Jezebel asked their readers to submit the absolute worst pickup lines that anyone has ever tried to use on them, and the results are predictably hilarious and mind-boggling. (Mind-boggling in the sense that there are people who exist out there who think the key to woman’s heart involves the phrase "smell your ass." Readers, it does not.)
All the top ten are pretty choice, but I think this one is my favorite in terms of the sheer imagery:
i was new to san francisco, so pretty excited when a few acquaintances offered to take me out to a (now defunct) bar/restaurant in the castro known for garlic fries and events for single queer women. i realize now that the two aren’t really the greatest combination (garlic breath and awkward introductions, mm), but i digress. anyway, as i’m sitting at the bar, trying desperately to make eye contact with a girl standing a few yards away, an older, clearly drunk woman slides up to my right. she looked fifty-ish, had clearly drawn on upside-down "v" eyebrows, and smelled STRONGLY of booze. when she started trying to make conversation, i smiled politely and continued eating my fries. i suppose she was a firm believer in "if at first you don’t succeed…", because she decided to place her hand on my upper thigh, squeeze and declare, "I AM THE LAST LIVING RELATIVE OF JOHN F. KENNEDY". which was confusing because a) i knew it to be untrue and b) even if it were true, i’m not sure why she would think that it would make me go home with her.
By the way, in my mind this women is an exact copy of Marsha from the British sitcom Spaced:
Reading the whole list is probably worth it, just in case you are unknowingly using a similar line and can now save yourself from future embarrassment. Luckily, my old stand-bye didn’t appear: "Hi, um… I… nice… [unintelligible]… um… drinks… your shirt." Kills every time.