"Why are we here?" Gabriel grumbled, pulling his jacket closer around himself against the chilly San Francisco breeze.
"Because, Gabriel. It's your first night in San Fran. As your host and amazing friend, I'm taking you to get some drinks and listen to some great music. Now stop your moaning, c'mon." Pamela snaked her arm through Gabriel's and led them into a classy lounge named "The Bubble Lounge".
Gabriel noticed the stage to the left of them and quirked an eyebrow at the group gathered around it expectantly.
Pamela made a beeline for the bar, which thankfully, wasn't crowded and returned with drinks.
"Do you know who's playin' tonight?" Gabriel queried, wondering if he's heard of the small-time artist. "You know how picky I am when it comes to music."
Pam nodded before sipping her drink "His name's Sam, I know his manager, great guy. Believe me, Gabe, you'll love him."
"Ready, kid?" Rufus asked gruffly. Rufus had been Sam's manager since his first days in the business.
"Always. Got the setlist?" Sam asked over his shoulder, looking at his suit in the mirror.
Rufus threw a laminated sheet of paper at him. All the songs they had agreed on the night before were highlighted in blue, except for Rufus' scrawl at the bottom.
"Summertime, Rufus? I thought we were doing this next week?" Sam raised an eyebrow.
"Yeah, well, Pam's got a friend in town and cashed in a favor I owed her." He responded awkwardly.
Sam chuckled "Alright, where's my mic?"
"Ladies and gentlemen, please put your hands together for the velvet-smooth crooner himself, Sam Winchester!"
The pack of women sitting front-row began to yelled excitedly as Sam stepped onto the stage.
The first thing that Gabriel noticed was his height. Sam Winchester looked like the fucking Chrysler Building compared to Gabriel's 5'7" frame.
"Good evening, everybody! Thanks for coming out tonight. We're gonna start it out a little slow. This is a special song for me because my mama used to sing it to my brother and I when we were kids." Sam smiled at the aw's he received "Hit it, Mikey."
Soft acoustic guitars began to strum out a gentle melody, followed by violins, piano, and upright basses.
"Stars shining bright above you, night breezes seems to whisper "I love you"" Sam crooned out and Gabriel was instantly glued to the singer. "Birds singing in the sycamore tree. Dream a little dream of me. Stars fading, but I linger on dear, still craving your kiss. I'm longing to linger till dawn, dear, just saying this. Sweet dreams till sunbeams find you. Sweet dreams that leave all worries behind you, but in your your dreams, whatever they be. Dream a little dream of me."
An hour and a half had passed and Gabriel's eyes hadn't moved from the chanter on stage.
"Well, folks. This is gonna be the last song for tonight." Sam's words were met with groans of protest, he flashed his winning smile that made Gabriel's heart melt "I know, I know. If I had it my way, we'd be here till dawn. This last song goes out to the lovely Pamela Barnes. Welcome back, honey."
Pam raised her shot glass in appreciation.
"Summertime and the living is easy." Sam serenaded.
Gabriel just about had a coronary as he turned to see Pamela grinning mischievously at him "You little shit." He said between gritted teeth.
"I couldn't resist! He's single and I knew you had a thing for the artistic type, plus Summertime being one of your favorites, I cashed in a favor to Rufus!" Pamela tried not to laugh at Gabriel's enraged face.
"You planned to set me up with Adonis himself? Jesus Christ, Pam. Give a guy a warning or something. Does he know?"
"Of course he doesn't know, you idiot."
Gabriel heaved a groaned and downed the rest of his drink.
Meanwhile on stage Sam bowed as the band faded out "Goodnight, San Francisco! Thanks for coming, y'all were amazing!" The crowd cheered wildly.
"Great show, kid." Rufus handed Sam a small towel and a bottle of water "Pam's by the bar."
"Would it be a bad time to tell you he's coming over here right now for drinks?" Pam bit her lip sheepishly.
"He's what?!"
Suddenly Sam's tall frame came into Gabriel's line of vision, he quickly looked away.
"Pamela Barnes!" Sam kissed her cheek playfully.
"Samuel Winchester. Long time, no see, boy. Amazing show, as usual."
"Thanks. And who might you be?" Sam's hazel eyes met Gabriel's amber ones
"I-I'm Gabriel. Gabriel Milton."
"Milton? Of the New York Miltons?" Sam questioned.
Gabriel chuckled "You caught me. Contrary to popular belief, we're not all pretentious blood-sucking lawyers."
A petite waitress places beers in front of everyone at the table and handed Sam a chair "So what do you do then?"
Gabriel relaxed and sipped his beer "I teach Dramatic Literature. Talk about the black sheep of the family."
Sam laughed "No kidding. Is that why you're in the Bay Area?"
"Gabe transferred from Brooklyn Tech to Lowell High." Pamela interjected.
"Needed a change of scenery, you know? I've heard fresh air does wonders."
Sam smiled "You kn-" He was cut off by a short Italian looking man "Ah, Alessandro wants me to meet some people. It was really nice meeting you, Gabriel." He quickly shook Gabriel's hand as he stared at the taller man dumbly "Pamela, a pleasure as always." He kissed her cheek goodbye and sped off.
Gabriel rested his head on his head and stared longingly after the man "I think I'm in love." He sighed dreamily.
Pamela laughed "C'mon, Romeo. Let's get you home."