To: My Mom
Scene: The Men’s department at Kmart, in the underwear aisle. A cute store clerk has overheard her ask me which size of briefs would fit better, the medium or the large.
What I said: “Large. No, medium, I guess.”
What I wish I’d said: “Don’t they make a size for people with elephantitis of the penis?”
*
To: Rita, my high school crush
Scene: The laundry room. She’s sitting on the dryer. Her dad will be picking her up any minute.
What I said: “I hope your dad comes soon. I’ve to get ready for the Dungeons & Dragons Battle Royale Tournament this evening.”
What I wish I’d said: “I hope your dad never comes to pick you up. That way we can stay here forever, my dear first love. Oh, by the way: I don’t play Dungeons & Dragons and I laugh at anyone who does. Now hold still while I kiss you passionately, which I am not at all afraid to do.”
*
To: Clyde, fraternity chapter president
Scene: The basement of a fraternity house. I’m being paddled ferociously.
What I said: “Thank you sir may I have another!”
What I wish I’d said: “You know on second thought, I think I’m going to find another group of friends with which to spend my time.”
*
To: Principal Stern
Scene: A school-wide assembly in the auditorium. Spelling bee championship.
What I said: “Phlegm. P-H-L-G-E-M.”
What I wish I’d said: “Phlegm. P-H-L-E-G-M.”
*
To: Anna, my college girlfriend
Scene: My bedroom. We’ve been dating for two and a half weeks.
What I said: “I think I’m falling in love with you.”
What I wish I’d said: “You’re really nice.”
*
To: Sean, the mean-spirited bartender at a restaurant where I worked
Scene: The restaurant where I worked. My last day there.
What I said: “It’s been great working with you, man. Take care.”
What I wish I’d said: “Your death will bring me joy.”
*
To: Lori, the mean-spirited supervisor at an office where I worked
Scene: The office where I worked. My last day there.
What I said: “See you around, Lori. Keep in touch.”
What I wish I’d said: “When I read of your death in the paper, I will weep from happiness.”
*
To: The blackjack dealer
Scene: Las Vegas.
What I said: “Hit.”
What I wish I’d said: “Stay.”
*
To: The bartender
Scene: A bar. I’m turning 21.
What I said: “FIVE SHOTS OF TEQUILA!”
What I wish I’d said: “For me? Oh, just a seltzer, please.”
*
To: The barista at Starbucks
Scene: Starbucks. She’s asked me what size cappuchino I want: tall, grande, or venti. She’s pretty.
What I said: “Grande.”
What I wish I’d said: “Don’t they make a size for people with elephantitis of the penis?”
*
Josh Lefkowitz (a) regularly saves puppies from burning buildings, (b) has volunteered in an orphanage on six different continents, (c) hasn't been to the gym in over a month, (d) all of the above, (e) none of the above, except (c).