It’s a rare occurrence when there is a straight forward question and answer between W and his friends. Typically the question is delivered in a multiple choice format, e.g., “Guess what was so-and-so’s excuse for not hanging out tonight…. was it: A) There is a professional family photo shoot in the morning; B) his mother in law needs him to take her to the gynecologist; C) He promised his wife he’d watch the So You Think You Can Dance finale live; or D) he has to go to the Gymboree graduation.” We all then get to weigh the validity of each statement, come up with our guesses, then inevitably laugh at the real answer.
I personally love it, and I actively engage in and love creating my own multiple choices. It’s even fun when it’s something as simple as guessing the name of the waiter (“Is it A) Jebediah; B) Orion; C) Darnell or D) Mikhail”).
Today I got to overhear W on the phone with our friend as he was figuring out the answer to one of the most fun reoccurring questions… “Guess who friended me on Facebook?” However today must’ve been a slow day at all the offices, because instead of multiple choice, he had Will play 20 questions.

Block out from 3-4 on your calendar… it’s time to play “Guess who friended me on Facebook”. Note: this dude is not an actual friend of mine
How I wish I the video recorder out, because W’s side of the conversation went along the lines of:
“Is it a girl?”
“From high school?”
“Our year?”
“What about our elementary school, did she go there?”
“Was she friendly with Mike?”
“Rachel Greenfeld!”*
“No? Ok. Um, Was she cooler than us?”
“Was she hot?”
“Is she still hot?” [lots of laughter while there is some follow through to this question on the other side of the conversation]
“Was she a cheerleader?”
“Um… Did you ever take her to see Les Mis?”
“OK, so she’s our age, was hot, may or may not have been a cheerleader, she is not friendly with Mike, you don’t think she was any cooler than us, and you never took her to a Broadway play… Danielle Adelstein!”*
“No? Hmm… what, am I at question 11? Did… she work in Sunrise Mall?”
“Did she work in the Gap?”
You get the picture… I don’t know if this translates, but I was hysterical. I highly recommend bringing back 20 questions to your day-to-day, it makes things more interesting.
* No names of known people were used in this blog post. If you are a Rachel Greenfeld or Danielle Adelstein who found this when you googled yourself, rest assured that this was a random concoction of likely Long Island Jewish girls names born between 1974- 1979.