She's having a baby. Or plans to have a baby, if he wishes to be more accurate. The fact that this is merely something she intends to do does not lessen his ambivalence. He assumed, over the years, that she decided to shelve the idea of becoming a mother. After he failed to assist her in adopting a child (and perhaps, he suspects, this is when her crush on him faded and shifted back to neutral, platonic territory) and he then became entangled in his own mess of love affairs. First to a woman who murdered her husband, then to a former childhood flame married to another man and then to a woman who rivaled him in terms of ruthlessness and aggression. All relationships disintegrated before they even truly began. But Liz Lemon is still very much in his life. And she's having a baby with someone else.

A lesser man, a man prone to indulging in self-pity, would lament the irony and the lost opportunity. But Jack Donaghy doesn't look back, only forward. So he is going to support his friend – and he must acknowledge that is all she can be to him now - as she embarks on this new exciting phase in her life.

But, on his way back to his apartment, he allows himself a moment to indulge in contemplating what a Jack and Liz relationship would resemble. He imagines, aside from his apartment being filled with Star Wars memorabilia- it wouldn't be much different than what they are like now. This realization doesn't lessen his malaise. He wonders why he never thought of this before. Why he allowed himself to become so obtuse and how he could not see the solution to his happiness staring right at him for six years.

He has no intention of acting upon his recent realization. He is through sabotaging relationships for his own gain and will not compromise Liz's happiness for his own. So when he arrives at his apartment, he gets into his bed and convinces himself that a life bereft of companionship is not so bad. He has Liddy. He has his job. He has Liz (for now – his brain annoyingly reminds him). He is about to fall asleep when his phone alerts him that he has received a text message.

Liz Lemon:

Hey buddy! Just wanted to make sure you're okay after today…I know you said you're fine but divorce is a bummer (even for guys like you who are made of Teflon). You'll find somebody awesome soon. Because you're pretty great.

He smiles sadly to himself and knows that Liz is wrong. He won't find somebody "awesome," because, sadly, he already has.

For the rest of the summer, he makes a conscientious effort to spend time away from Liz in an attempt to establish distance from her (also, witnessing her look at Criss adoringly has spurned pangs of jealously within him that are decidedly unpleasant and unbecoming for a man of his stature). During this time, he sleeps with no fewer than 8 different women, over half of them under the age of 35.

Usually, a night spent in the arms of a flexible, blonde dance student at NYU was once a very effective prescription for heartache, but now he finds these incidents leaving him empty and wanting for something more substantive, or at the very least, searching for a connection that goes beyond the woman's ability to reenact his favorite pornography scenes.

The morning TGS is scheduled to begin its 7th season, Jack mentally and emotionally prepares himself for Liz to barge into his office and regale him with whatever hijinks are already ensuing on her floor. As if on cue, Liz does come barreling into his office looking disheveled and stunned. He looks up at her from his desk expectantly, awaiting for her to launch into the most recent TGS horror story.

Instead, she holds up her left hand and Jack sees a rather large glistening stone on he ring finger. "Criss proposed to me." She declares in a shocked, hushed whisper.

"I see that. Just now, I take it?" He says evenly, forcing his tone not to show any sort of emotion.

She nods in response, her eyes still wide with surprise. "Yeah. After breakfast. He made pancakes and then just slid this box across the table like it was no big deal and then he got down on one knee…"

Jack holds up his hand to interrupt her - he's heard enough of this pseudo-romantic proposal. "And you said yes."

"I did. I'm gonna be a wife." The realization of what she just said dawns on her and she collapses onto the couch. "Oh God, I'm going to be a wife. Me! Did you ever think that would happen?" When she notices his smirk, she adds, "Don't answer that."

He gets up from his chair, crosses over to the bar and pours a couple glasses of champagne for them.

"This shouldn't be that shocking to you, Lemon. As I recall, you were married once before. To someone quite extraordinary." He smiles smugly, while handing her the glass.

She rolls her eyes at his conceited reference to himself. "Yeah, but this time, it's not because of some stupid clerical error. The dude actually wants me! Can you believe that?"

Jack can't help but smile sadly at the irony. Their fake, ridiculous marriage was only one example of the slew of chances he had with her. Only one of the many missed opportunities. He realizes doing anything now to undercut her happiness, at such a late stage in the game, would be beyond cruel.

"Absolutely. I've been waiting for the day to make this toast with you."

Liz beams in response, and gently clinks her glass against his. She frowns when she notices Jack's eyes narrow at her ring finger. "Good God, Lemon. Is that…a zirconia?"

Jack grabs her hand in order to inspect the ring and Liz extracts it from his grasp defensively.

"He can't afford a real diamond right now! He said he'd replace when he has the money…"

Jack rolls his eyes, "You mean when he has access to your money. Once you get married? I hope you plan on having a pre-nup drafted."

"A pre-nup? Seriously? This is what you want to talk about the day of my engagement?" She shoves her glass into his hand, causing much of it to spill over the rim and onto his fingers. "I can't believe you. Not everything is about money, Jack."

"Even love isn't exempt from being related to money, Lemon. I know this from painful and expensive first hand experiences. You need to be sensible. This man – if you can call him that – doesn't have a cent to his name. What's to stop him from marrying you for a couple years, knocking you up and then taking you for whatever he can get?"

"So that's the only reason Criss could want to marry me? Because of money?"

Her voice hitches and Jack runs after her as she hastily rushes out of his office. "Liz, that's not what I meant…I just think you deserve someone who can provide you with a ring that doesn't pass off as costume jewelry."

She lets out an exasperated sigh, "I'm finally happy, Jack. After so many years of being miserable. This ring may be a piece of crap. But nothing has ever made me happier. And if you can't handle that…then I guess you won't be coming to the wedding." Jack opens his mouth to come up with a rebuttal, but Liz immediately turns on her heel and briskly walks to the elevator. Leaving Jack alone and confused in his hallway.

This certainly wasn't how her first day back to work was supposed to go.

Before lunchtime arrives, Jack goes down to Liz's office and tentatively knocks on her partially open door.

"Yeah?" He hears her mutter distractedly and he slowly pushes the door open. When Liz sees that it's him, she immediately sits up straight and her body stiffens in her chair. "Oh…hi."

"I came to make amends." Jack announces somewhat apprehensively. "You have my full blessing, you know that. I just get…protective of you."

She looks off to the side and her lips twitch into a slight smile. "I know. But the whole point in me being married is that you won't have to go all out of your way to do that anymore."

"I think I'll always want to be protective of you. Regardless of your marital status." His eyes are fixated on hers when he says this and he does relish in a certain pride that her face lights up at his comment.

"That's really sweet, Jack. And creepy. But mostly sweet."

"I think the best declarations of the heart are usually a mixture of both." They share a smile and he places his hands on her desk and bends down to say in a hushed, conspiratorial whisper, "Let's play hooky and celebrate."

"Hooky? What are we 15?"

"We can have a ridiculously expensive lunch. See a movie. Then I'll drop you off at home where you can burn off the hundreds of calories of saturated fat you've consumed with your fiancée."

"That does sound kind of awesome." She concedes, biting her lip.

He grabs her jacket hanging by the door, holding it open expectantly. "Come on, Lemon. What's the point of being the boss unless you can be a little reckless from time to time?"

"I'm sure the execs at Ernon said the exact same thing." She says with a sardonic smile as she hops off her chair and lets Jack drape her jacket over her shoulders.

Naturally, he takes her to one of the most expensive restaurants in Midtown. Since she is wearing a fitted black dress instead of her usual plaid attire, he's relieved he doesn't have to concoct a far-fetched and elaborate story in order for her to be allowed in. This is another reason; he reminds himself, that he cannot consider Liz Lemon as a potential mate. A girlfriend of Jack Donaghy, at a minimum, should always be ready to accompany him to a formal dinning establishment without advance notice.

But during lunch, this rule of his seems to wash away as she describes her summer, wedding planning with Jenna and their attempts to convert her second floor to the nursery. Her anecdotes are a mixture of side-splittingly funny and adorable and Jack realizes that he's never had this much fun with a member of the opposite sex. The conversation between them is easy, effortless, almost as if they are already a couple and have been so for years.

During a lull in the conversation, Jack takes a moment to fish a small black velvet box out of his pocket. "Ah, Lemon," he clears his throat and chuckles nervously, "I want to give something to you."

When he presents her with the box, her eyes fly open in shock, "What the what?"

"Don't worry, it's not a proposal. I merely find the idea of a woman as unique as you walking around with a fake ring exceptionally upsetting. You deserve a genuine ring. So I've taken the liberty of purchasing one for you." When Liz opens the box, she sees that it looks exactly like the one Criss gave her. "It's an exact replica of what you're already wearing. So Criss won't notice the difference."

"But you'd notice the difference?" She asks with a quirked eyebrow.

"When a man gets engaged four times, he tends to pick up a thing or two about diamonds. I think you'll find that the one I'm giving you is a rather impressive."

"But, I can't accept this. This ring probably cost more than my first car." She gasps.

"You never owned a car. And the cost is irrelevant. Think of it as an engagement present." He gently grabs Liz's hand and slowly takes off the ring Criss originally purchased for her. When she doesn't protest at his action, he takes her silence as a sign of permission to replace Criss's ring with his own. His fingers slowly glide the sparkly piece of jewelry down her finger and Liz can't help but acknowledge that this ring looks much better than a cheap piece of plastic ever would.

"Wow." She murmurs, staring at the ring in front her.

"So…you like it?" He asks unnecessarily.

"It's beautiful, Jack. Thanks. I have to admit…I feel like I'm really engaged now." Her awed fascination with the ring prevents her from noticing Jack's melancholy smile. Jack never thought he'd ever pine for a woman who is already taken, but he realizes that by buying an engagement ring for another man's fiancée, he's doing just that. Unfortunately, he also comes to the conclusion that he does not have enough conviction to stop himself from being so utterly pathetic.

"So, care to take a walk and show off your new piece of hardware to all the gold diggers in New York City?" He says, offering his arm to her after he pays the bill.

She snickers and eagerly slides her hands around his arm, "There's nothing I'd like to do more, Donaghy."

With that, they exit the restaurant and walk arm and arm in the crisp autumn weather and to any other observer in the restaurant, it would appear that the city has just gained another happily newly engaged couple.