From Jessica, by way of McSweeney's.... Thank you.
Too fucking hilarious.
A N O P E N L E T T E R T O M Y F I R S T F I V E G I R L F R I E N D S .
June 16, 2004
Dear Holly, Kathy, Kelly, Nicole, and the other Kelly,
Look, I'll come straight to the point. I'm sorry I didn't know where the clitoris was, or, more to the point, where your clitorises were. I was a horrible wreck of dry humping, fingering teen lust who pinned you to couches and carpets and danced all around your deserving buttons of love without so much as grazing them, without even inquiring as to the location of your hidden high-school treasure, without even thinking that you might not be liking the way I was swizzling my hand around in your nether regions.
You were patient with me. You let me slip you the tongue in the field behind the shopping center. You allowed me to reach second base in the bathroom at Phil's party—you remember, the one where we drank all that peach schnapps and watched The Wall on Phil's mom's big-screen TV. Heck, you sat still in the back of Scott Parsons' sweet-ass Honda Prelude while I rooted around in your shorts like a frat boy working a couch for spare change.
While I'm at it, I'm also sorry for letting Brandon smell my fingers. That was immature and uncool, and even though you never found out, I feel badly about it. Really, I do.
To be honest, you should be pissed at my dad. We never "had the talk." I had no diagrams to work from, no explanation of the intricate workings of the little man who steers the canoe. Everything I knew about sex was gleaned from Cinemax's presentation of Emmanuelle in Bangkok and this old Betamax porno Bobby stole from his dad. I watched the latter one three times. Other than making me uncomfortable to be around my dentist, it didn't help.
I asked my father why he never clarified the finer points of clitoral massage with me way back then, but he just said that wasn't really part of polite conversation and he'd prefer not to discuss it. So I asked him if he knew where Mom's clitoris was and he hung up on me. I took that as a no.
Anyway, sorry about that. I'd have done you right if I'd had any idea what we were both missing.