A/N: This idea was floating around Tumblr and, honestly, one of the more talented and experienced authors should be writing this. However, this is my take on it. I regret nothing.

Part One

The Group

"Are you ready for tonight?" he whispered in her ear. He stood to the side of her; she was nearly as tall as he was.

"Absolutely," she responded. Her lips curved to show two rows of perfectly white teeth. Don and Sloan had been planning this date for about a month. It is their…fifth date, Sloan thinks.

"Well, what are you two hiding?" Mackenzie asks as she walks out of her office. They've been going out for a few months now and they are the newsroom's favorite power couple.

"Oh, we're just planning our big date." Don beams with pride as he says it. He may be getting the hang of this good boyfriend thing. Being cheerful feels natural, almost effortless.

"Oh!" Mackenzie's voice picks up, "That's lovely!"

Mackenzie hasn't been on a date in a few months and best friend Sloan knows it. She catches the nostalgia in Mackenzie's voice, the slight loneliness. "Do you want to join us?"

Don's jaw drops, but he quickly recovers, "That might not be the best…"

"Are you sure? I wouldn't want to intrude." Mackenzie's eyes turn hopeful. This could be what she needs to turn things around.

"Absolutely!" Sloan responds.

"Not!" Don chimes in, the worry wearing deep in his face. He feels his breath leave his chest and the blood to his head. He didn't expect company and he surely doesn't want it.

"Invite Will. It can be a double date. That'd be fun." Her straightforward nature is taken aback by her sheer innocent exuberance. A double date with her 'older brother' would be amusing, to say the least.

"Dinner with colleagues," Mackenzie gently suggests. She's fluttering with happiness. It feels like she hasn't been out to dinner in forever.

A flabbergasted Don leaves the room to go do paperwork. He can't say no to Sloan. His mind is fried and he must digest that which just occurred. He sighs, "Women," and shakes his head.

Will

"Ah, fuck." He has not done this in years. Will regrets parading the models and ingénues through the offices. The idea that it would succumb to an evening with coworkers never crossed his mind, but he has to atone for his grievances. He scours through his rack of clothing to find something, anything that he can wear. "Is this just dinner? Fuck," he curses as he thinks to himself. Secretly, he wants it to be. Will desires to be with Mackenzie, but his heart still aches. He pulls out an old Gucci suit and finds a gold watch stored in his dresser. Will quietly scoffs. After a quick shower, he throws on some light cologne and looks at his refection. The old eyes staring back at him speak hurt and nervousness. He wipes the emotions away and grumbles. "Go big or go home," he mutters as he walks out the door.

Mackenzie

She runs her fingers through her hair and sighs. When memories rush at Mackenzie's senses, she sits down on the edge of the bed. Will, wine, food, dates, it's all so distant but here she is. Mackenzie invited Will to a dinner with Don and Sloan. The red-haired executive producer thinks she noticed a hint of a smile on her news anchor's lips. He required coaxing but she got him to agree to go. The closet in her bedroom is distraught with shoes and clutter. "It's a dinner between friends," she tries telling herself as she stands up and looks at the pile of dresses on the chair. She pulls a red dress off a hanger and puts it on over her black lingerie. "Just friends," she murmurs as she takes out a new pair of lacy black heels. Mackenzie checks her make-up in the mirror, clutches her purse, and walks out the door.

Don

He's had his outfit planned out for a week. Don has a clean, black suit hanging in his closet ready to wear. The black shoes are laid out on the floor, freshly shined. He combs his hair and smiles in the mirror. Old Spice may be cheap, but it's highly effective. Will and Mac's eccentric history isn't going to throw him off his game, not tonight. He tosses a few fresh rose petals on the mattress. He chose pink, not red, petals.

Sloan

Thud…thud. Shoes sail out of the closet and hit the carpet with soft thuds. First goes a pair of red wedges followed by purple kitten heels. Sloan isn't known for her skills in organization. On her hands and knees, she scours her closet for the special occasion shoes. Bringing Will and Mackenzie along won't be so terrible. They all need to get out of the office, the big stories they've been reporting have left the crew weary and restless. Blowing a piece of hair out of her face, she smiles, holding up a pair of black stilettos. "Got 'em!" she whispers excitedly. A black dress gets pulled over her head and she slips on the heels before running, stumbling, out the door.

The Restaurant

Will, Mac, Don, and Sloan meet outside a little restaurant up north. Its bright lights and Italian herbs make it a hotspot for evening get togethers. A few patrons walk out, their night slowly coming to a close while this group's night is just beginning.