A Wink And A Wave

I work from awkwardness. - Diane Arbus

I was in a meeting the other day with my boss. We were just discussing life and scheduling and such. Joy (my manager) comes in with a kid about my age who apparently is our roofer - as in, he's repairing our roof. My boss, who likes to make things awkward - just for the fun of it - pointed to me and told the kid, "See? Here's one you can date." Then he turned to me and explained, "My wife keeps trying to set him up with our daughters..." -turning back to the kid- "But you can date her, too."

Obviously things were pretty awkward at that point, and so I decided to ... well ... enhance that embarrassment. I got this cheesy grin on; I winked, and then I wiggled my fingers flirtatiously at him. Not joke. Smile, wink and wave. I thought he'd laugh and we'd move on, but he completely clammed up. And I about died - of repressed internal laughter. He thought I was serious. Not only would that make me an absolute social retard, but the fact that he believed my sincerity would indicate that he suffers from some sort of quasi-narcissism. He didnt look at me for the remainder of the time in the room, and I think I pretty much traumatised the kid.