Story Time: Rolex Guy

Because my blog is all about love, relationships, and well……………..ME! (Pretty narcissistic, eh?) Anyways, because my blog is about my experiences, I thought I would share one of the worst dating disasters I have allowed – minus the one that inspired this very blog!

We had met downtown, where I work & where he was visiting for a nationally held conference. He was funny and really nice surprisingly for a guy who was handsome as he was. When he asked me to lunch the following day, I said yes. Originally, the plan was to dine at an upscale steak house that was in between both of our locations.

Because I was wearing heels and didn’t want to make the trek passed blocks of homeless people that occupy the bus stops, he offered to pick me up.

The way his shiny Mercedes pulled up against my building’s curbside, should have been red flag number one into how our lunch would play out. I should have reversed my steps back into my building taking the elevator back to my office and into my chair where I should have text, Cough Cough, I’m sick- I can’t go. (Mean Girls classic btw.)

But he was nice. And funny. And handsome.

Yeah, right!

His shiny Mercedes pulled up and my legs climbed in. He was on the phone talking loud and fast, then texting so much as if he was about to close a business deal. I sat there studying my surroundings. A Rolex decorated his wrist, as he drummed his arm on the wheel I saw he had GOLD cufflinks, red bottom dress shoes and Ray Bans covered his eyes.

After his “business”, he slid his glasses off and smiled a bleach white smile he probably paid thousands for and his green eyes danced in the sunlight as he apologized and proceeded to drive onwards the restaurant. I gave him the best driving directions I possibly could as downtown is a complicated maze of tourists, business people, cyclists, traffic and the horridity of multiple one way streets.

On the way, we passed a bar in which he tried convincing me to go to mid-day. Of course, I just smiled and said no thank you. To which his reply was to further convince me that a couple of drinks would be fun and fine in which he went from insistent to pushy. He decided he didn’t want to go to the steakhouse. It was too pricey.

Annoyed but not upset, I obliged and we settled on chain restaurant. We got off the car and walked across the lot, he hurriedly and I struggling to not get caught in the cobblestone. Entering the eatery, we were directed to a table and again he tried to convince me to dine at the bar. I sat down unmoving so he would understand that I would not change my mind. Heaving a sigh of annoyance, he sat across me and started texting, making calls due to “business.” He ordered an assortment of alcoholic beverages for himself while I sipped a water. During the few minutes of conversation we had in which we talked a bit about national news, politics (I know right?) and even the weather. It is when I should have punched him in the face when he stated:

“I didn’t think you would be smart.”


“I mean for a pretty girl you’re really smart.”

Did you just say what I think you said?!

“Take it as a compliment, a gorgeous girl like you-normally, beautiful girls aren’t smart.”

It only got worse as the lunch progressed.

He kept trying to snap at the waitress while I chided him like a misbehaving child to not do so. He started slamming the table instead only aggravating me worse. He talked about being an only child and living in Europe, life with a nanny and other bullish lies. He took out thick wads of hundreds and started counting them at the table when the bill came, only to display an AMEX and confide in me he only brought me because he was going to expense my lunch as a company charge. All of this within twenty minutes of dining at the restaurant because upon seating, he exclaimed he had thirty minutes to eat before needing to meet his boss.

When leaving, the hostess stood outside and against the door, he waited a few seconds before pushing the door hard against her and leaving me to apologize profusely for his jerkish behavior. I was mortified.

We got in the car where again he tried to use his poor power of persuasion to get a drink with him. He poured me with compliments which only met eye rolls. Finally having enough, I dished it back to him and he was quiet before laughing and saying that I’m quite sassy.

A block before my drop off, he asked me to dinner in which I laughed and said no. I was one and done. He was not used to being turned down, or so he says.

“More like hit it and quit it. My car windows are tinted, we can go to a parking lot.”

I met his response with a slammed door of his Mercedes. Which of course, was probably rented just like his cheesy suit and tie.

He texted me a little later in the day saying he had the best time ever.

I did not.



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