Introductory note: We don't see pretty much anything from what happens between when Will dumps Nina and is given the Goldilocks planet lecture from Sloan up to the final red team meeting in September. Sloan lectures him and then we don't really see him until the next episode which is 6 months later! Gah! How did he react? And did anyone else notice Will is being maybe oddly flirty with Mac? "Someone would be have to be torturing you" in order for him to admit who his source is or "you are the most beautiful person I've ever seen in real life" and in the meeting about Sweeney's TBI the two of them are sitting closer than normal...not too mention the first episode of the season with him sitting in the hall during her deposition prep!

Of course they aren't together (after the Sweeney interview they are shown at their separate apartments) but maybe...just maybe...that proposal wasn't so completely out of left field as it seemed...

This starts the night after Will dumped Nina.

Mac walked in to Hang Chews, her stride stuttering when she recognized a familiar figure sitting at the corner of the bar nursing a whiskey.

She glanced to the side, looking for the rest of the staff. It was still only 10:20 so it would be an hour before Don or Sloan arrived and although Neil, Tamara, Gary, Tess and Martin were in their customary booth Jim was no where to be seen.

Mac weighed her options before taking a breath and situating herself on the stool next to Will and ordering her drink.

He tipped his glass in silent greeting.

"It's been a while since you've come out after the show." She observed, her insatiable curiosity winning over her brain's instincts to not mention that he was alone at a bar on a Friday night when he had steady girlfriend.

He responded with a shrug, not moving his focus from the television set where Elliot was recapping the day's events.

Mackenzie took a sip of her drink, eyes roving around the bar, trying to not be discomforted by the quiet. Despite her inner voice demanding she just enjoy her drink in quiet it was not long before she surrendered to her own need to break the silence . "Is Nina going to be okay with you sharing a late night drink with your ex-girlfriend or should I go sit with the rest of the staff?"

She mentally kicked herself as soon as the words fell out of her mouth. She tried to keep her regret from showing, even as she watched Will tense.

He glanced over at her, eyes sweeping across her face, "I prefer to think I'm sharing a post-work drink with my EP as opposed to a late night drink with my ex-girlfriend." His tone was soft but pointed.

Mac nodded. "Of course."

They were quiet for a minute until Mackenzie couldn't help but stick her foot in her mouth again, "So is Nina out of town?"

Will rolled his eyes, keeping his attention in front of him.

Mac shook her head, "I'm sorry, I shouldn't..."

"I broke up with her." He interrupted.

Mackenzie blinked, "What?"

Will looked at her and smirked, "Nina. I broke up with her."

"Okay..." Mackenzie immediately felt torn between her compassion for Will as a friend going through a break up, her excitement at the break up, and her morbid curiosity as to the why of the break up.

Despite the fact that Mac was pretty sure Nina was the first girlfriend of any length or significance that Will had had in the past 5 years he did not seem to be upset about it at all.

In fact she could swear there was actually a ghost of a smile on his lips as he explained. "It needed to happen. Honestly never should have been with her to begin with."

"Still, break ups suck." Mackenzie offered in friendly commiseration.

"Some more than others." Will responded automatically, glancing at Mackenzie briefly before swiftly returning his eyes to his drink. "This was not one of those." He tossed back what was left in his glass.

Mackenzie let the silence sit for a moment, forcing herself not to react to the subtext of his comment. Instead she cleared her throat and asked, "When?"

He shrugged, "Yesterday morning. After the morning show fiasco."

Mac nodded, "Was it bad? Should I be on the look out of any tell-all articles coming out in the gossip rags?"

Will groaned and looked at Mac in askance, "God I hope not. I don't think she would but then again I guess I should think a little more carefully before abruptly dumping a gossip columnist who has written plenty of bad press about us."

"Or dating one to begin with..." Mackenzie murmured into her drink.

Will grimaced. "I deserved that. You're right. Like I said it was wrong."

She sighed, and decided to try and force herself to offer comfort as if she were speaking with anyone other than Will, "It couldn't have been all wrong; you were together for a while." She offered gently.

Will fidgeted with the coaster in front of him, "I think I was just trying to convince myself that I'm capable."

"Of being in a long term relationship?" She clarified, unable to contain a small, cheeky grin.

"Of being in a relationship with anyone but you." He mumbled, not looking up until the words were out of his mouth and he could sense Mackenzie freeze beside him.

Shock and hurt flashed across her face before she gave a sad shake of her head and shifted off the stool, "Oookay. Well. I don't know why I though we could talk about this. I'm going to head over to where the staff is sitting..."

"Wait." Will stood, blocking her ability to leave her stool. "That came out wrong. I'm sorry. Forget I said it. Sit? Please? Have another drink with me?"

Mackenzie took a deep breath and again cursed herself as she felt her resolve weaken against the power of Will's eyes earnestly locked on to hers. She nodded once without smiling and resituated herself on her bar stool.

She fiddled with the edge of her glass before glancing to Will who was watching her with barely masked trepidation.

"What did you mean by that?" She finally asked.

Will looked to her and opened his mouth to speak when the television screen caught his eye and he closed his mouth. He turned his attention up to where Sloan was doing her segment on Elliot's show. Will narrowed his eyes at the image of young anchor before taking a big sigh and mumbling a barely audible, "Alright..." to himself.

"Will?" Mackenzie pulled his attention back to her. He met her eyes, glanced back up to Sloan's face one more time before focusing entirely on Mac.

His tongue came out and wet his lips and she watched him war with himself internally before he explained, "I think that was trying to convince myself that I could be in a relationship with anyone else...but I failed. It's time for me to just admit that I'm not capable of being in a relationship with anyone other than you."

Mackenzie's eyes went wide but Will didn't give her an opportunity to speak or otherwise react, "Maybe I've always known but I'm just now accepting that fact so I'm done playing that game."

Mac's brow furrowed together and she asked the only question her brain could articulate, "What game?"

Will shrugged and glanced around the other people in the bar, "You know. The 'Let's date and pretend we're compatible' game."

Mac shook her head, "So you're saying because it didn't work out with Nina that you're swearing off dating?"

Will rolled his eyes, "No. I'm saying that because of, well, may be a little bit because of Nina, and something Sloan said, and Habib, and just because I've been thinking...whatever, it doesn't matter why. What I'm saying is that I'm not going to lie to myself that there is even a chance that I could be happy with someone who isn't you. That happens to mean no more dating because it doesn't feel fair leading people on. Not to mention, it seems kind of pointless to date when you already know that you'd be happier somewhere else."

Mackenzie pulled her mouth into a tight thin line as she relaxed back into her chair, placing her drink back on the bar and regarding Will with a long, critical look.

"What am I supposed to do with that information?"

He shrugged and turned his attention back to the bar, avoiding eye contact.

"What ever you want. I don't know what to do with that information or how I feel about it." He glanced to her briefly, "All I can tell you is that I think that subconsciously I might have come here tonight because I was hoping you might show up." He kept his eyes focused down on where he was rolling his glass between his hands.

Mackenzie nodded slowly and mimicked him, turning to fully face the bar, digesting his words. After a moment of silence she raised her hand to grab the bar tender's attention.

"He'll be wanting another drink and I'll have another in a few minutes when I'm done with this one."

"Do you want to start a tab?"

Mackenzie glanced over to Will to see him watching her. She turned her attention back to the bartender and nodded.

"Yes, I think we're going to be here a while."