Disclaimer: Dont own OUAT. wish i did but i dont.

A/N: i was going thru some OUAT photos and i saw that someone said that if Emma were a guy then SQ would totally be endgame. That got me thinking What If she were one... Ladies and Gentlemen i give you my first fanfiction of SQ. Please be nice thank you:)

Regina's POV

It has been 18 years to the day that the curse has been cast. 18 years of ruling and solitude. 18 years of the same monotone. I need to get away, at least for a day. I can't take it anymore, just a little break will do. I packed a bag for at least a week. I won't go that far just, away. I called secretary telling her I will be out this week. She can manage for me, not like there is a lot to do. I get in my car and drive away. As soon as past the Storybrooke sign I let out a breath I did not know I was holding. This is what I need, just some away time. I drove and drove and drove until I got to Boston. I don't know exactly how I got here but that is not important. It is enough for me.

I find a hotel to fit my needs. I go up to my room, freshen up, and unpack. I looked at the time, 2:00 pm. I should go out and get to know this city. I went out and found a restaurant, decent food. I spend my time walking around in a park I found. Thinking thinking thinking… I went back to the hotel, when I got a call. It Katherine, I wonder what she wants.

I answer "Hello?"

"Hey, Regina. Are you ok?" Katherine asks, worry laced in her tone.

"Im perfectly fine, dear. Thank you for asking"

"Okay, just making sure. You weren't in the office today and skipped our lunch today"

Damn, I forgot about that.

"Im sorry, I had business in Boston. I won't be long."

"Oh okay, then when you come back then."

"Yes, dear. That will be fine."

"So Boston eh?"

I sigh "Yes, Katherine. Boston"

She chuckles "well if you are looking for a distraction from all that business then I suggest The Poison Apple"

"The Poison Apple?" I smirk a little at the irony

"Yeah, it is said to be the 'it' bar nowadays."

A bar? She is sending me to a bar?

"It is not a low class bar Regina. I know you enough for that." Katherine answers my thoughts

"Well I might just check it out. Thanks Katherine."

"You are welcome. Have fun. Talk to you when you get back"

"Goodbye Kathrine."

"Bye Regina"

Hmmm… I should see this Poison Apple. Maybe it is exactly what I need.

I go to the closet to find something suitable for my outing. I pick a personal favorite. A one shoulder, mid-thigh, black dress. I take out my red four inch pumps and a red clutch. Yes, this will suffice. I get in the shower, something much needed. I enjoy the way the water sprays on my back, I relax a little. I get out and dry my hair. I put on my dress and go to the mirror to put my make-up. Smoky eye and blood red lips. Perfect. I put on my heels and coat. I get to the lobby and ask the clerk there about The Poison Apple.

"Oh good choice ma'am. I will hail a cab for you if you want."

"Yes, please. That will be great"

I got in the cab and saw the lights pass by. This is what I need. A distraction. I finally arrive at the bar. Its name in flashing green lights with a red apple. I still smirk a little at the irony

I walk in "Good evening ma'am. Welcome to The Poison Apple." Someone takes my coat

"Thank you" I walk to the bar to see the bartender tossing up a bottle of liquor and catching it behind his back.

"Impressive" I tell him

He smiles "Thank you. What can I get for you?"

"An Apple Martini, please."

"Coming right up"

I look around the bar. It is dimmed lighted a lot of red and greens. The taste in decoration is not the bad actually. Katherine was right, she does know me. Smooth jazz was coming from the speakers around me. I closed my eyes and breathe in. Yes, this is what I needed.

"Here you go ma'am." The bartender handed me my drink.

"Thank you" I went to pay my drink

"Oh no ma'am. Someone already paid for you." He pointed his head forward. I followed his gazed and saw who had paid. A young man with sea green eyes and blond hair. He looked shockingly familiar. Ha, how can he be familiar if he is from this world? He smiled at me raised his glass, as in to say cheers. I raised my glass to and drank. I turned around and kept drinking. I ordered another one and paid.

"You should have let me buy you this one too" I jumped a little in my seat. I turn to see the blond stranger next to me.

"It is not necessary. I can afford my own drinks." I reply

He chuckles "Attitude, I like it." He stuck his hand out "by the way, my name is Emmett."