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The Bold Bitch Diaries | Part One: Gorgeous Greg

Hey loves.

This is a story about a girl named, Lucky.

JK JK no not really.

This story derives from my own life, my own experiences, my own spinsterhood.

It all began at a housewarming party for a good friend of mine. I don’t like to use the real names of people in my life, so let’s just call her Lana. Lana is a beautiful mess, so naturally we are obsessed with each other. My (best) friend Penny was there as well, she and Lana go way back.

Upon entering Lana’s home to engage in the festivities, I instantly see Penny chatting it up with some hippy boy at the beer pong table. I wouldn’t expect anything less (love her). I could see glimpses of Lana’s gorgeous big hair bouncing in the darkness of the backyard as I peered through the sliding glass door. A bearded fellow by the name of Charles came up from behind me and introduced himself. He asked me my name and I told him, “Robert” but he insisted he’d call me “Robby.” As he stumbled away, I saw Lana’s friend/roommate, Jessica casually sitting down on a bar stool with a FUCKING SNAKE AROUND HER NECK. HELL NO. ROBBY DON’T PLAY THAT SHIT.

“Come pet my snake!” said Jessica. “Her name is Delilah.”

MY ASS WAS ABOUT TO RUN FOR THE HILLS BUT THEN…I saw something else I wanted to pet.

Sitting across from Jessica was a scruffy and enchanting 6-foot specimen of a man with wavy black hair accompanied by a gray beanie. His skinny jeans proved to be fitting for a guy like him, who’s tall slender stature exuded a sense of know-how, confidence, honesty, and safety. At the same time, his spiked boots and gauged ear lobes offered an edge that I thought was instantly attractive and carried the possibility of aggressiveness.

Who is he, I thought.

“Isn’t she sweet?” the gentleman asked. He carefully petted Delilah so naturally I decided to do the same. I didn’t want his first impression of me to be “What a pussy.” I smiled, and laughed off my nervousness, something I thought could be turned into a charming quality.

As I slowly walked away, I turned to Penny.

“Who is that?” I asked. Penny chuckled and whispered in my ear.

“That’s Gorgeous Greg,” she said.

* * *

I lay restless on Lana’s bed. Lana, Penny and Lana’s cousin Jen sat around me as I carefully constructed a plan — except there was no plan. I knew what I wanted and I wanted it tonight. I hadn’t even been kissed in four years though so how the hell was I supposed to make a move on a guy who is known by friends as “Gorgeous.” I mean, it’s in his fucking name.

As I moved around the house, mingling with other guests, I would brush up on him here and there. I would try to strike up a conversation but I didn’t know how to hold one about indie rock music. That’s just not my thing. But let’s be real, it’s not like I was trying to date the guy.

Lana, Penny and Jen really wanted something to happen, almost more than I did. They showed support by encouraging me to slowly move my way in and see if Gorgeous Greg was even into me.  Lana’s roommate Jessica is best friends with him so Lana had some inquiring to do.

“He said he thinks you’re cute!” Lana whispered in excitement.

As happy as I was to hear the news, I still had no idea what to do about it. And it appeared that Gorgeous Greg didn’t either.

It was getting late and I knew I had to go home soon. I decided careful planning was unnecessary at this point. As I was saying my goodbyes, I saw Gorgeous Greg. I went in for a hug and as I leaned in, I said, “Would you mind watching me out?”

Cigarette in hand, he said, “OK,” and then looked to his friend. “Hold this,” he ordered, and handed her the cigarette. I waved toodle-loo to Penny, Lana, and Jen and they waved back in approval. I walked out the front door to the silent neighborhood and Gorgeous Greg followed behind me. I turned around to face him as he shut the door, and that’s when I did it.

I went in for the kill.

It’s really difficult to make out with someone who seems to be a whole foot taller than you. But gratifying, it was. We locked lips for a good five minutes and then I pulled away slowly. I grinned.

“Thank you. Goodnight.” I said, and then walked away into the night. I said fucking “thank you.” I didn’t ask for his number, I didn’t even try to get his last name to add him on Facebook. I got what I wanted. And for the first time in my life I was bold enough to do it myself.

After four long years of involuntary spinsterhood, there comes a time in your life when being bold is the only option you have left. And in that instant transformation from being scared and afraid of every little thing that has held you back all this time, you will be set free. Every time that you avoided the mirror, bailed on a party invite, skipped out on a job opportunity, or turned down someone you liked because you didn’t think you even had a chance will all be seen as a waste, and no longer will you let anything stop you from getting what you want and being who you are.

Thus, the beginning of the Bold Bitch Diaries.

xoxo Robby Rob

Bold? What ever do you mean?

Bold? What ever do you mean?

Robby Rob talks “Gorgeous Greg” in Episode One of DOAGS: A LOOK INSIDE.

Read More Bold Bitch Diaries:

Part Two: The Homemaker and the Homewrecker
Part Three: Regina George



  1. Pingback: Announcements, March 2013 | Diary of a Gay Spinster

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  4. Pingback: The Bold Bitch Diaries | Part Five: The Final Chapter | Diary of a Gay Spinster

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