Last summer, I was with my friends Whitney and Megan when Whitney asked us to accompany her to a bar near her Upper West Side apartment. Whitney was new to online dating and wanted us to join her in loosening up over libations, then leave shortly after her date arrived. We obliged.

We found a nook at Gin Mill when Megan asked “So, what does he look like?”

“I don’t know” confessed Whitney.

We both snapped at her “what!?”

“He didn’t have a picture… but I figured, he’s 6’5″ so…”

I nearly choked on my drink. “Whitney! Always make sure they have pictures, or ask them for their Facebook profile so you can at least make sure they aren’t trying to hide something.”

Megan shook her head with disapproval “Well do YOU have your pictures up?” Whitney not only had put pictures of herself on the website, but gorgeous ones from a recent, professional photo shoot she had just taken with Canadian photographer, Phil Crozier. “Well,” she continued “let’s just hope he doesn’t look like Shrek.”

“Stop it!” yelled Whitney “…and guys? Please pretend to be laughing at some hysterical joke I just told when he comes in. I want him to think I’m funny.”

“But you ARE funny” said Megan. “I’m sure we can fake a good laugh for you.”

“So… what does he do?” I asked.

Whitney’s eyes slowly scanned to the floor. “He’s currently unemployed, but he volunteers at a hostel for housing…”

Megan nearly choked on her cocktail. “WHITNEY!”

“What!? He wrote me and asked me out. What was I supposed to say… no?”

We both stared at her for a second before yelling “YES!”

“Ugh… okay,” said Megan while staring out the window at the line of arriving patrons. “Let’s guess which one he is.” We had fun for a few minutes guessing the most awkward of dates for Whitney. Megan then spotted an unsightly fellow walking on the sidewalk with unkempt hair , severely weathered clothes, and a quality I used to bestow upon children’s book characters I like to call cheese mouth. Again, I was a strange child, and found that nearly all illustrated characters in my books who weren’t the antagonist looked like they ate pounds and pounds of cheese without ever brushing their teeth. “Oh My! Whitney… can you imagine if thats him!?” We all laughed and teased her at the thought.

Whitney rolled her eyes. “Stop that! Thats mean…” We realized the man was now making his way for the bar, and, he was significantly taller than everyone else in the line to get in. “Oh. My. Goodness… thats my date.”

The reaction Megan and I shared, while wholly inappropriate, was luckily just what Whitney had asked of us before her “gentleman caller” arrived.

“Hi, I’m Earl.”

Megan and I both had tears streaming down our faces while we made our introductions between laughing spasms over our friend’s unfortunate online date choice. Whitney was not laughing.

My attempt at salvaging the moment would probably have failed with anyone else. “She’s just… so funny! This girl!”

“Well,” Megan gulped the remaining three quarters of her cocktail “Jacob was JUST going to walk me home. Nice meeting you! BYE!” Megan and I ran out of the bar faster than a herd of antelope trying to avoid being eaten for dinner. I looked at Megan”What!?” We slowed our pace “we would have stayed laughing like that all night and you know it!”

“True.” I turned back to see Whitney looking out the window like a family pet being left in the kennel while we went for a vacation some place exotic. Megan and I stopped for deli sandwiches

“Note to self…” Megan unwrapped her Philly Cheesesteak. “Whitney is not allowed to set me up on blind dates.”