Drawing My Dates: Red Wine and Olives

Did I blow it by talking about Shirley Temple?

Drawing by Jay Boucher. Print available.

I figured I’d blown this online date right at the start by talking about Shirley Temple. For some reason I began our conversation by describing the song “On the Good Ship Lollipop” and how the 1934 movie “Bright Eyes” had 5 year old Shirley Temple dancing on a crowded airplane with a bunch of grown men as they handed her lollipops and patted her face with powdered sugar and melted chocolate.

“Totally creepy!” I exclaimed and she looked at me blankly. She was a lawyer and I found myself unable to read her expression, but it didn’t look good. I spent the next five minutes recovering and I must have done a decent job because we hung out the next couple hours, drinking red wine and sharing a plate of olives. A quick hug goodbye outside in the rain and that was the last I saw of her.

Buy the print