Not-So-Smooth Operator

Story Sent in by Evelyn:

A red flag in the case of Leroy was that he signed all his emails, "The Smoothenator." When we met in person, he had two pairs of sunglasses on. And it was nighttime.

He told me, "I might need you to help me walk."

I suggested, "Maybe you should take your sunglasses off."

He replied, "The Smoothenator leaves his sunglasses on. Even in the shower."

"Why?" I asked.

"Because the Smoothenator paid for waterproof glasses."

He wore his glasses at dinner. The waitress asked if he wanted a braille menu. When he told her he could see she gave him a funny look but said nothing more. When he ordered his dinner, he told her, "The Smoothenator will have the chicken parm." He also ordered for me, saying, "The Smoothenator's girlfriend will have the Caesar salad."

When the waitress left, I corrected him: "I'm not your girlfriend."

He pointed at me and said, "You are the Smoothenator's girlfriend."

I asked, "What if I don't want to be your girlfriend?"

He said, "Then why is the Smoothenator wasting time with you?"

"For a nice time and conversation?"

Leroy laughed and said, "The Smoothenator cares not for such things."

We split dinner and went our separate ways. I planned to ask him if he was going to drive home at night with his sunglasses on, but decided that I didn't care.


  1. I'm amazed that you agreed on a date in the first place... I would have thought that red flag would be quite an indicator of what he had in store. Always easy with hindsight though, isn't it?

  2. OP doesn't know how lucky she was... Sometimes, Lord Chunky Horse takes the form of The Smoothenator to walk among us mortals...

  3. I absolutely would have gone on this date and seen it through if only to tally how many times he said "The Smoothinater."

    1. Gasp! I'm appalled, Bananas! People don't exist solely to provide you with amusement and entertainment!

      Now, where were we? Oh yes, comment secks...

  4. If she paid for her own dinner, why the hell would she let him order for her? Amber has a good point, why would she meet him in the first place?

    1. Maybe he asked her what she was going to order and just told the waitress.

  5. Anyone else think his nickname stemmed from a case of misheard lyrics?


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