The suavely dressed ex-lawyer nursed a glass of Scotch slowly. He made sure his lips never made contact with the ice cubes flowing around the liquor. He had specifically asked for the bartender not to put ice in the glass as it diluted his drink and was probably riddled with bacteria. With his god like body, he never wanted to take any chances.
Setting his glass down on the glossy wooden table, he nodded nonchalantly at his company.
The bubbly brunette was on some rant about a recent article in Teen vogue. He didn't pay her no mind as she complained about how Maybelline's lipgloss didn't suit her glowing skin.
Conversations like this always made Jeff Winger feel older than he should. Or at least like some sort of sexual predator.
His date was in no way a child, in fact, she had just turned 22, but her mentality rubbed him the wrong way.
Why he chose her wasn't for her supple, young flesh, but based purely on her looks and socially desirably.
Jeff knew this. There was no doubt about it.
Jeff loved the idea of him being able to bed a beautiful, young woman. If a woman society holds up among others deemed him worthy to sleep with, then Jeff Winger was a God.
The only thing better than publicly broadcasting that he was in fact, the man, was if he was able to reject or dump the woman. But past experiences deterred him was doing that again.
He continues to nod mindlessly at her banter, looking at the other bar-goers past her. A few middle aged office workers nodded approvingly at him and a Frat Boy raises a glass in respects to the honorable Winger. To these men, he was a hero.
But God were her stories boring.
It was always like this. Sometimes the women were worse, but it was always like this. Sometimes he hated it, but he knew he needed to be seen as the best. If he didn't, his narcissism would nag at him to prove otherwise, which usually ended in trips to the gym or one-uping his friend Duncan.
Jeff wanted to roll her eyes as she complained about her ex-boyfriend and quickly downed the Scotch. He internally noted that when he got home, he'll have to drink more if he wanted to go through with this.
He never fully enjoyed the sex, but the validation. He loved hearing his company swoon over his abs or compliment him on his performance. Even if he got nothing out of it sexually, hearing that he was the best his company ever had was satisfying enough.
"So then my friend Mandy told me that Uggs were back in and I told her that Uggs were always in," The Brunette explained before taking a sip from her pink beverage,"But whatever. Enough about me, and my day. How about you? Anything interesting going on in your life?"
Jeff lived for moments like this. He loved boasting about himself. The study group, having known him for so long, have gotten used to his antics. They were no longer bemused by Jeff's shopping and fine dining because they knew that Jeff would just insult them for not being as cultured as him. But his dates always found his life captivating.
"Well," Jeff started with a smug smile,"I was feeling chilly this morning so I bought a goose jacket from Bloomingdales. Online of course, because I'm a very busy person."
"What were you busy with?" The Brunette asked with wide, curious eyes.
Jeff was stooped for a second. Usually his dates take his words at face value. Now he'd have to think about an answer that didn't sound like a complete lie. It's not like he could tell her he spent the day working out, watching television, and staring at himself in the mirror. And he definitely couldn't tell her he was a student at Greendale Community College.
"I..I was working," He spat out,"I had a lot to do at the office and then I had to help a few friends out at the community college. Old colleagues who fell on hard times."
Not exactly a lie, but also not exactly the truth.
"Really?" The Brunette's eyes softened and she rubbed Jeff's hand,"You're friends are lucky to have you."
"Well, I am a gr-," Jeff began when he was interrupted by a pop ringtone.
"I'm sorry," The Brunette pouted,"It's probably Mandy. I'll be back in a bit."
She took off in the direction of the bathroom, before fully disappearing from view.
He knows he shouldn't, but Jeff feels more at peace without her talking about nonsense or old lovers.
Jeff basted in his mental nirvana for five minutes, when he heard glass shatter. It came from the direction of the bar, but Jeff didn't want to concern himself with trivial drunks.
That was until a familiar voice peaked his interested.
"I lived in New York. I can handle a few more drinks!"
Even with the words drunkenly slurred, Jeff knew it belonged to his blonde activist counterpart, Britta Perry.
Sighing, the annoyed Winger turned to see that Britta was leaning onto the bar for dear life as the nervous Bartender swept up her broken glass.
Jeff always found drunk Britta amusing, but he also knew how much of a pain in the ass she was to innocent bystanders.
Normally, a drunk Britta would needlessly argue about politics with people who never engaged in conversation with her. Other times she cried about how she thought her cats might not love her anymore, but this was different.
Instead of Britta being the typical train-wreck she was, she seemed different. She seemed genuinely hopeless.
Jeff was going to walk over and give Britta a hand when he noticed the Frat boy from earlier had beaten him to it. Mildly angered someone else got to play the hero role, Jeff went back to waiting for his date to reappear.
It felt like hours as Jeff pretended to text on his phone. He was starting to think that his date had crawled through the bathroom window to escape him, but that was absurd. Who would want to escape from the perfect man?
Stealing glances from the corner of his eye, he noted that the Frat Boy had grown close to Britta. A ping of jealousy slithered through Jeff's thoughts, but he quickly brushed it away. Even if that pathetic Frat Boy made a move, Jeff knew Britta would lecture him about sexual harassment and how misogynistic he was.
Britta could Britta anything.
"I have to go ask a man about a horse," Britta loudly announced to the entire bar before making her way to the Ladies room. It took a while since she couldn't walk in a straight line, but she made it there with relatively no bruises.
Jeff laughed to himself at the sight, then pondered on sending Britta a text message asking if a Brunette was with her in the bathroom. Though the idea was creepy, Jeff couldn't fathom the concept of his date bailing on him.
The negative thought chewed away at him. It wasn't until he made his way to the bar that the intrusive thoughts dulled.
Jeff didn't drink to cope with stress. He never considered himself an alcoholic and refused to become one. Liquor just made him less tense. The fact that Scotch made him look sophisticated was an added bonus.
Grabbing his freshly topped off glass, Jeff scouted the room for a potential new date. Like hell a catch like him was going to say single in a crowded room.
He eyed down a deliciously beautiful Red Head in a green maxi dress. She looked mature, but in a Angelia Jolie kind of way. But what made him want her was the admirers drooling over her from afar.
As Jeff planned his strategy to woo on the Red Head, he noticed a familiar figure put something in a drink.
Redirecting his attention, Jeff's eyes widened in fear. The Frat Boy had slipped something in a glass of vodka with two olives.
As if on cue, Britta returned and quickly grabbed the Vodka.
It felt like time had slowed. Jeff was stunned at the sight of Britta putting the glass to her lips. Before he could get his voice to call her name, he already slapped the spiked drink out of her hand.
"Wha..Jeff?! Oh nice to see you here," Britta gave him a dopey smile and leaned into his chest to catch her balance.
"Nice to see you too. Hey, I have an awesome idea," Jeff's voice was friendlier than usual. He didn't want to set her off. A livid drunken Britta was violent in very possible way.
"I'm always up for ideas or whatever," She muttered into his chest.
"How about I take you home and we'll order take out. Your choice," Jeff replied as he wrapped his arms around her protectively.
"Listen Bro, she's with me," The Frat Boy shouted at Jeff.
The Frat Boy tried to intimate Jeff with a menacing look and knuckle cracking, but he didn't care. No matter how much of a sleaze Jeff was, he couldn't let a woman fall prey to a predator.
But this didn't deter Jeff from taking precautions. Jeff didn't want to get into a fist fight, since he had little experience under his belt. He didn't know if this guy was packing a weapon, but Jeff didn't want to find out.
"You seem like a reasonable man," Jeff lied effortlessly,"How about I give you $200 and you leave my friend alone."
Jeff took two hundred dollar bills out of his pocket and handed it to the man. And like how Jeff planned, he took it without much thought and left them alone.
"I think I want. Um. Pizza. Yes. Let's get pizza," Britta continued to mumble into Jeff's shirt.
"Fine. Let's get Pizza," He ran his hand through her blonde hair lovingly,"We can even order those weird Vegan desserts you like."
With Britta's hand, they maneuvered through the overflowing bar. Every now and then, Britta would stumble but Jeff was quick to catch her. Even when she was close to hitting her head on a table corner, she laughed it off.
Outside Jeff escorted her to his Lexus and childproof locked the doors after she got inside. He knew she'd yell at him for it, but right now he needed to do something.
Jeff made his way to the Security Guard outside of the bar, handed him $500 and informed him of the man spiking women's drinks. The Security Guard promptly called the police, then went to handle the predator personally.
Jeff watched as the Security Guard roughed up the Frat Boy without remorse. When the police came and arrested the man, Jeff smiled.
By the time Jeff had gotten back to his Lexus, Britta had fallen asleep. Her head was leaning against the window and her hair was covering her face. Sliding into the driver's seat, Jeff buckled Britta in and checked her pulse.
Still alive. Good.
Smiling to himself, he pulled out of the congested parking lot and made his way to his apartment. A night in with pizza and movies weren't Jeff's cup of tea, but he could manage if that meant Britta was safe.
AN: Sorry for the typos. I'm typing this at night. I wanted to write a fic that conveyed Season 2 Jeff's mindset since you don't see much of that. Thank you for reading.