For once in his life, he doesn't know how to interpret a woman's intentions. Usually, when a woman invites herself into his bed – no matter how coy the invitation – there is an implicit agreement that some form of sex will take place. But he knows Elizabeth Lemon. And, as such, he knows that she doesn't have a coquettish bone in her body and her aversion to sex would usually preclude her ever initiating it. If he understands the way her mind works (and he believes he does, there is perhaps no other woman whose thoughts and he behaviors he knows so intimately), Liz is truly looking to share a bed for strictly platonic purposes. The idea that she wants to be with him in such an intimate context and doesn't even entertain the possibility of anything sexual occurring bothers him a great deal. To most women, his presence in a bed is noticeable and palpable; he is, after all, virility personified. But apparently none of that works for Liz because she is able to view him as a stand-in for the boyfriend that left her.

His internal musings are interrupted when he hears a quiet knock on his bedroom door. He turns around in bed to see Liz in the doorway, awkwardly pulling his t-shirt down at the hem as much as she can.

"Your shorts were too big…so I didn't leave them on." She explains shyly. His eyes drift down to how his t-shirt barely covers the top of her thighs and skims just below her hips. He doesn't think he's ever seen her wear so little and the sudden visual imagery catches him off guard. "Ah, that's quite alright, Lemon. I should have figured those wouldn't fit you." He attempts to say as nonchalantly as possible.

"Are you grossed out by me being almost naked?" She cringes, "I can go into the guest room. Or sleep in my jeans…"

"Don't be ridiculous. You will not be sleeping in the guestroom and I loathe seeing women wearing jeans on the street, much less in my bed."

"Okay, cool. The upshot to all this is that I got my legs waxed the other day, so you're getting a very unusual hair-free Lemon experience." Jack watches her crawl into bed and true to her word, she stays as far away from him as possible. So much so, that half of her body is practically dangling in mid-air.

"Liz, you can move in a bit. I promise I won't bite." She gives him an appreciative grin and scoots a couple inches closer to him. At this point, they are both on their sides facing each other. He's not sure what to say exactly. He's never been in bed with a woman without the promise of something else occurring.

"Your sheets are really nice." He smiles, leave it to Liz to mention the most mundane detail in a situation in order to offset the tension.

"They are Egyptian cotton. I'll bring you a set for your apartment. Everyone should sleep on sheets like these."

"Oh, sweet. Thanks." She grins and after an awkward silence adds, "They smell good too. Like lavender."

"I'll be sure to let my housekeeper know you find her selection of laundry detergent satisfactory. Is there anything else you'd like to say about my sheets?" He teases liltingly, poking fun at her attempt to fill the silence with her unnecessary observations.

"No." She scoffs.

"Go to bed, Lemon."

"Sounds like a plan. Good night, Jack."

The long business trip, mixed with the alcohol allows Jack to fall asleep quite quickly, but Liz's constant tossing and turning beside him interrupts his slumber.

"Lemon, what's wrong?" He grunts, forcing himself to open his eyes.

"Sorry. I'm really bothering you, aren't I? I should go to the guest room." He quickly wraps his fingers around her wrist to prevent her from leaving.

"If you tell me what's wrong, I can try to fix it."

"I guess it just hit me that Criss and I our done. And…I'm really going to miss him, Jack." The somber tone of her voice in the darkness, makes Jack feel for her pain while envying this other man who doesn't deserve her.

He inches closer to her and props his head up with his hand so he can look down at her when he says, "I doubt you two are really over. Usually abrupt break ups like these rarely hold water. He'll most likely come crawling back and apologize for speaking rashly."

"Really? You think so?"

"I don't know Criss that well, but that is usually how these things go."

"I hope you're right." She sighs. "I still can't sleep."

"There is something I could do that would make you fall asleep immediately, but you have to just go with it and trust me." He says cautiously and can't help but notice Liz smirking back at him.

"You're not going to drug me, are you?"

"No, nothing like that." He then swiftly pulls her body toward him so they are practically spooning. Liz's gasp of surprise quickly turns into a moan when his hands massage and glide over her shoulders. "I find that women typically find this relaxing."

"Um…yeah, this is good." She murmurs.

"So I may continue?" Her face is buried in the pillow and, upon hearing her muffled consent, he begins slowly massaging every inch of her back. Touching her like this, without being able to take things further, without being able to undress her, without being able to feel her skin, is a certain kind of torture. But he can see how much she's enjoying this, and giving her pleasure is something that has become a matter of instinct these days.

It doesn't take long; barely 10 minutes have passed before she is asleep in his arms. Her body securely tucked against his, her face resting on his arm; the naturalness of how their bodies are situated makes him convinced more than ever that this is exactly how the two of them are meant to be, that this is how they're supposed to end every night and not just this one. This is Jack's last coherent thought before he too, surrenders himself to sleep.

He stirs groggily in bed when he hears Liz settle a glass of water by the nightstand. "I didn't mean to wake you." She grins, sitting back down on the bed beside him. "Your housekeeper gave me some aspirin and I brought some for you – figured you needed it." She hands him the water glass, which he gratefully accepts and she gently places the two pills in his palm. His eyes rove over her and frowns in disappointment when he sees that she's fully dressed in last night's attire.

"You don't have to leave so soon. Stay for breakfast."

"Aw, I'm sure what you have here blows anything I have in my apartment out of the water, but Criss is waiting for me." Jack tries to maintain a sense of calm when he notices the sheer happiness radiating from her – a happiness that has nothing to do with him.

"Is that so?"

"Yes! You were right. Well, you're always right. I don't know why I'm surprised." She smiles bashfully and rests her hand affectionately on his arm. "It looks like I'm not doomed to be alone forever after all. Yay!" She playfully rubs her hand up and down his arm, and Jack forces himself crack a smile. "You okay there, buddy?" She asks, her eyes narrowing at him in concern.

He's not used to being used as a prop in a woman's love life, but he supposes that's exactly what he's become – a mechanism for Liz to turn to for comfort when her personal life is in disarray. He never thought he'd ever lose to a man like Criss -a man with no prospects and little substance. For once in his life, Jack is flabbergasted that his good looks, charm, intelligence and inordinate wealth does him no favors with winning over a woman. And in the battlefield of love, he has lost to a more handsome, younger, kinder version of Dennis Duffy.

"Ah, yes, I'm fine, just had a tad too much to drink." His chest expands when he sees that she is looking at him so affectionately, so lovingly, if there was a time to make any sort of declaration, he knows that this moment would be it. But knowing that another man is responsible for a rather significant portion of the elation she is experiencing would render any revelation or confession completely unwanted and maybe even a tad pathetic.

"I'll walk you out." As he gets up from the bed, Liz protests at his gallant act of showing her out the door, but he ignores her. Mostly, he insists on escorting her to the door because it's what you do when a woman spends the night at a man's place. But mostly, he wants to savor being in her company -her being in his home -a little while longer. When they reach his threshold, she explains that she will go home to shower and get dressed and then meet Criss at a coffee shop in order to talk.

"Is it okay if I show up a few minutes late for work, then?" She asks.

"Of course. But, Lemon," he begins, "perhaps you should make him sweat it out a bit. Don't you think agreeing to meet with him so soon after he decided to break up with you is a little too forgiving?" After he says it, he knows he overstepped his boundaries, but Liz doesn't seem angry with him or put off.

"Ah, the whole games and manipulation thing is your bag. I'm a lot simpler. I just want a dude who loves me and that I love back." He wants to tell her that she already has that, that he wants to provide that for her and everything else she could ever want, but before he can say anything she enthusiastically wraps her arms around his neck and plants a firm kiss on his cheek.

Whispering against his ear, she murmurs, "Thanks for last night, Jack. I don't know what I would do without you."

She turns to leave, but before she rounds the corner to the elevator, Jack hastily shuts the door behind him and follows her.

"You might have to." He says loudly, his voice echoing down the hallway.

She turns, confused, "What?"

"You may have to know how to cope without me. Because…Criss is going to forgive you, but he's also going to insist that you maintain a strictly professional relationship with me."

She takes a few steps toward him, her head cocked to the side, "Why? He knows we're just friends."

He pauses, and then begins to speak cautiously; knowing a slight misstep in his words can cause irreparable damage to their friendship. "I'm going to say something now. And I want you to know, if you don't agree with any of it, we can pretend like this conversation never happened."

"Oh boy. Do I need to sit down?" She looks around and, frowns when she sees there is no place to sit in his empty hallway. "I really wish your hallway had a chair." She mutters staring down at the floor.

"What I'm going to say is not meant to upset you in any way. " He takes a deep breath; gently lifts her chin with his index finger so his eyes fixate on her and says, "Criss will want you to sever all personal ties with me because he thinks I'm a threat. And I am."

Her jaw drops and she glares at him angrily. "What are you talking about? Nothing happened last night."

"Doesn't mean I didn't want it to. Doesn't mean that I didn't want to kiss you. Hold you." He steps even closer, his eyes smoldering as he says, "Make love to you."

"Jack – shut up." She whispers, her voice strained. She looks up and her eyes are shining and he can tell she's trying her best not to cry in front him. "You tell me this now? Why didn't you say anything before?" He is about to respond but she shakes her head vehemently. "No. I don't want to hear it. You're too late, Jack. You're six years too late."

He doesn't stop her from turning on her heel and rushing further down the hallway to his elevator. He doesn't know why he even attempted to say anything at all. She is engaged to someone else. Even as a middle-aged man he can't seem to shake his romantic inclinations with regards to love. Normally, he has no regrets when he chooses to wear his heart on his sleeve – after all, when he does so it rarely ends in an unmitigated disaster. He simply should have let Liz marry the man she loves. Maybe then, he would at least still have his best friend.

He numbly walks back into his apartment, and braces himself for what is bound to be an awkward day at the office. He is at his table, sipping his morning coffee and reading the paper. None of the words on the page register, the coffee is bland and the food on his plate is untouched. When he hears a knock on his door, he assumes its Avery with Liddy. He makes his way to the foyer and stops in shock when he sees Liz holding Liddy.

"I bumped into Avery in the lobby. She said she was in a hurry so she asked if I could bring Liddy up." She mutters shyly as she gently sets Liddy down on the floor. Jack can't help but smile as Liddy scrambles over to Jack eagerly, her hands eagerly encircling his leg. He hoists her up, but his eyes remain focused on Liz who is restlessly shifting from foot to foot.

"Thank you, Liz." He nods. There is a thick, awkward silence in the room and Jack isn't sure what to say. "Liz –"

"I just want to make sure we're on the same page here - you're in love with me?"

"Very much so." She nods quickly, her brain obviously trying to come to terms with this news.

"But more than that, I want you to be happy. It's a goal I've been working tirelessly toward ever since I met you."

"You think you can make me happy?" She asks sharply.

"I would certainly like the chance to try."

"I want a family, Jack."

This response doesn't faze him. "That is hardly a secret. Even the man who makes your subs is aware of your desire to procreate."

"You up for that, Jack? The whole thing? I don't just want to be some failed experiment in your dating repertoire."

"I'm offering the whole package here, Liz. No half-measures."

"Yikes. You must really love me."

He smiles, and even Liddy seems to understand the weight of the moment because aside from the soft sucking of her thumb, she doesn't make a sound. He steps closer to her, bends down, and upon seeing that there's no resistance from her, he places a light chaste kiss on her lips. Liddy, in a phase where she is copying everything she sees, leans forward and kisses Liz's face as well, causing Liz to giggle.

"See? Even Liddy is on board." He chuckles and Liz's hands brush over her lips, unable to conceal her smile.

"I need time, Jack. This is a lot to process."

"Take all the time you need. We'll be right here." With that, she decisively turns around and exists the living room. Jack stares at Liddy and unable to contain his joy that there is hope with Liz, he lifts her up in the air gleefully before setting her down in her play area. The minute he rights himself, he feels someone sharply poke his shoulder. He turns around, only to find a smirking Liz standing in front of him.

"Screw it." Before he even begins to comprehend what she plans to do, she wraps her arms around his neck and pulls him down for a deep kiss. "Promise me I won't regret this, Donaghy." She warns him sternly, after breaking away from the kiss, but the grin on her face completely undercuts the tone of her voice.

Smiling, he's convinced he's never made a promise so eagerly and quickly in his life, "You have my word, Lemon."