A/N: I'm baaaack :) Y'all are so wonderful and supportive and encouraging, so I cranked out another little something (it also helps that I'm obsessed with this couple). I'm hoping to post a couple of different scenarios where there could've been a "moment" between our favorite couple and expanding upon it. Please excuse any canon mistakes from the show; I searched for a couple of things and couldn't find solid confirmation. If you spot something factually incorrect, let me know :)

I borrowed some dialogue from some other eps to fit the moment, so if it seems familiar, you know why.

This vignette takes place between 1.05-1.07.

Thanks so much y'all! Enjoy.

Despite his best efforts, Charles Brooks could not stop thinking about Diana Trout's new assistant. There was something special about her, something in addition to the fact that she seemed to have herself much more together than Diana's previous pack of assistants; give her another week and she would have outlasted them all.

No, there was something else. It seemed her literary knowledge was far above someone of her age, like she was wise beyond her years; an old soul. But perhaps he was feeding too deeply into the negative millennial stereotypes. It was entirely possible for a young person to be well-read, he supposed.

In just a few minutes of knowing her, she had checked off many of his favorite and "must read" authors: Chinua Achebe, Chimamanda Ngozi Adiche, and Thomas Wolfe, though she did not know he had see her devouring Look Homeward, Angel, along with her lunch. None of those books were secret, cultish sleeper hits only to be discussed by devoted bibliophiles, but to have insightful knowledge of all three was not a common occurrence; not in Charles' experience anyway.

He was curious about what else she had read, big and small. He had grown up around books as the grandson of Empirical's founder, but had thoroughly enjoyed comics just as much, if not more, than classics or best-sellers when he was a kid. He found himself wondering what this young woman would think about his love of comics.

He shook his head to clear his mind of these thoughts, realizing he couldn't even remember her name to ask. Diana had barked it during their meeting, but he had been so focused on dodging the marketing director's advances then masking his shock and delight when the assistant had shared her book knowledge. What had Diana called her? Lila?

As if on cue, when he stepped out of his office to refill his coffee, he heard Diana call out, "Liza!"

Liza, he thought triumphantly. Liza.

Liza intrigued him more than any woman had in a long time, despite only knowing her for a few hours and speaking less than five sentences to her. He wanted to know more…but how? How could that happen without him seeming like the creepy older boss coming on to a young assistant?

Just talk to her, a voice in the back of his mind told him. You can have a conversation without being illicit.

So he did talk to her, as much as he could without appearing overly interested. Professional-level interactions only. But though he learned small bits and pieces, it was still not enough; he needed more.

As with most things, the opportunity presented itself when he was least expecting it. In rare form, Charles ventured out to a young, hip party on the advice of a friend, although he was considering rescinding the "friend" label the longer he wandered around the modern and very lavish soirée. It was not a value judgment, but nothing about this party was his taste. The food, the music, the attendees…it was all much too far outside of his comfort zone for him to relax and enjoy himself. He was on the verge of calling it a night when he spotted her.

"Hey, I know you. You work for Diana Trout."

He tried his best to focus his gaze directly on her face, even though every manly instinct within him was desperate to examine every inch of the stunning beauty before him.

She smiled at him awkwardly, clearly uncomfortable."Well obviously I work in publishing for love, not money. Buzzy navel?"

He was confused momentarily but quickly realized she was offering him one of the drinks on her tray.

He took an obligatory sip of the sickly-sweet concoction. Liza could tell he was not a fan.

They made polite conversation, wherein Charles found himself telling Liza, who was practically a stranger, about getting out more after his divorce.

The understanding in her eyes and the tenderness of her voice caught him off guard. It appeared to stir something in her as well, as she stumbled to explain her insightful comment regarding divorce. Then, when she turned to go, she ran smack into another patron, spilling her tray of drinks everywhere.

Clearly mortified at having embarrassed herself in front of not one but two of her bosses, she bolted for the back room to get her things and leave.

Much to her surprise, she found Charles waiting outside for her.

"What are you doing here?" she asked, feeling perplexed.

Charles smiled. "I thought now that you're off the clock you could use a drink."

Please let her say yes, he prayed inwardly. He did not want her to feel uncomfortable going out with her boss, but after the spectacle he just witnessed, he felt it was the least he could do to brighten her evening.

To his great pleasure, she laughed and nodded. "You could not be more correct. Thank you."

He stepped aside, moving closer to the curb and gestured, "After you."

They walked in companionable silence to a cafe not far down the street, and as they did so, Charles couldn't help but notice how different she looked in her everyday wear. Not bad different; good different. Very good, in fact. It was odd to him, how striking this woman could be in a simple outfit, especially compared to the tiny uniform she had donned just minutes before.

He held the door open for her as they entered the cafe and insisted on treating her.

"Please, let me," he said, pulling out his wallet. "You deserve it after the night you have had."

She groaned and put her face in her hands. "I can't believe you saw that. I can't believe anyone saw that. I thought I might die of embarrassment right then and there."

Charles gave her a sympathetic smile. "It was pretty bad."

Liza laugher at this. "Gee thanks, boss. Good to know you don't gloss over the hard stuff."

Charles felt himself redden slightly at her referring to him as, "boss." He hoped again that their after-hours interaction was not making her feel uneasy.

"Thank you for checking on me," she told him warmly. "And thank you for bringing me here. If you hadn't, I would have spent my night reliving that humiliating spectacle and worrying about what you must think of me now. This is a nice distraction."

So she's a mind reader in addition to all her other positive qualities, Charles thought amusedly.

"You don't need to worry about my opinion of you," he reassured her.

"Oh really? So what do you think about me?"

Oh my god. Did I really just flirt with my boss? she kicked herself internally.

Charles was grateful their drinks arrived at that moment, saving him from making a fool of himself trying to appropriately answer her question. Fortunately, each of them was eager to move on to another subject.

Their conversation at the party had been courteous and somewhat stiff, but now the words seemed to flow more easily between them.

Once you've thoroughly embarrassed yourself by spilling drinks all over the place in a ridiculous outfit, there's not much left to lose, Liza thought. She also found him surprisingly easily to talk to.

They covered a myriad of topics: all things literature (of course); their favorite New York eats; the best places to visit outside the city; and they even ventured further into their personal lives.

Charles tried his best to be on alert throughout the evening. The moment she seemed uneasy, he was prepared to bring their night to a close. But that moment never came. In fact, it seemed like she had shifted closer to him as the evening had progressed. She hadn't checked her watch or her phone. She hadn't moved around uncomfortably in her seat. Logically he knew she might still be staying out of obligation, so as much as he didn't want the night to end, he offered to call her a cab.

"Oh do you need to get home?" she asked, seeming surprised.

He was equally surprised. Did she want to stay? "No," he shook his head. "I just don't want to keep you from…anything. You seem like you've recovered from the incident nicely, if there's somewhere else you want to be."

Liza gave him a small smile. "There isn't."

The feeling of elation coursing through him threatened to overtake his face in the form of a huge grin. He used all the power within him to suppress it into something more casual.

"So you have two daughters, right?"

Charles nodded. "Nicole and Bianca."

"Who is watching them tonight? Not that I'm questioning your parenting!" Liza clarified quickly. "I was just talking, not thinking."

Charles tried to put her mind at ease. "No offense taken. They have a nanny." He grimaced. "She's wonderful, but having someone else spend so much time with my kids instead of me isn't how I want things to be. But since their mother left…it's the only option I have until I know if she's coming back."

Liza noticed he said "if" rather than "when." She constantly worried about how Caitlin was handling the divorce, and she was significantly older then Charles' daughters; she couldn't even imagine how difficult it must be at their age.

Before she could stop herself, she placed her hand on top of his and gave it a sympathetic squeeze. "You're doing the best you can for them. That's all you can do."

Charles felt like his skin was on fire. He struggled to find the words to reply. "Are you sure you're 26? You seem to have better understanding and wisdom than people my age."

Maybe it was the small amount of alcohol she had consumed. Maybe it was exhaustion kicking in. Or maybe it was how comfortable and safe she felt in his presence. Whatever it was, after the evening they had shared, Liza felt compelled to tell him the truth.

"Can I be honest about something?" she asked nervously.

Charles let out a small chuckle. "After everything else that's happened tonight? I'm surprised you feel like you even have to ask."

Liza took a deep breath.

"Back at the party…" she hesitated. Was she really going to do this?

Yes. Her conscience pushed her onward. "Back at the party, when you told me about your divorce?"

"Yes?" Charles quirked an eyebrow at her, very curious as to where she was going with this.

She steeled her nerves and continued, "I said I knew the first few months of divorce are the hardest because I've read a lot of novels about divorced characters. That's not exactly untrue, but it's not…" she paused again and took another deep breath. "It's not really the truth either."

"I'm…not sure what you mean," Charles replied honestly. He hadn't thought anything of her explanation before; he knew she was well-read, so her book-knowledge on the subject seemed like it was logical. How else could a woman her age know anything about divorce? Maybe her parents…?

"I know about divorce because…because I'm going through one. Right now."

Charles gave her a quizzical look. "At 26?" He supposed it wasn't outside the realm of possibility. She might have gotten married young (maybe too young, it seemed). After all, over half of marriages end in divorce, as he knew too well.

She shook her head. "No. I was married for nearly 20 years."

He didn't understand. "This doesn't make any sense."

Liza sighed and closed her eyes. For the first time since they had met, Charles saw something different in her face. The tiredness in her features made her look…not old, but definitely older than 26.

"How old are you?" he asked simply.

When she opened her eyes and looked at him, he could see the fear in her eyes. "I'm…40."

40?

He would've laughed if the situation were happening to anyone else but him.

"40?" he repeated aloud, reeling with disbelief.

She pulled out her purse and handed her driver's license over to him. Her birth year was just a few years after his own.

"40," she confirmed as he handed her ID back to her. "I'm a middle-aged mom from New Jersey in the midst of a messy divorce."

"Mom?" Charles echoed. "You have children?"

At this, Liza seemed to relax somewhat, a small smile crossing her face. "Yeah. One daughter. Caitlin." She scrolled quickly through her phone and sheepishly passed it over to him, a picture of her daughter filling the screen.

"Wow," Charles said. "She's lovely."

Liza blushed, taking back her phone from his outstretched hand. "She looks more like her dad, but she acts a lot more like me." Liza paused, trying to think of what to say next. "She's why I'm doing this. My husband gambled away all our savings and her college fund. We paid off most of his debts when we sold our house, but her study abroad payments came due and I was out of options."

Feeling emboldened by the fact that Charles had not fired her on the spot and raced for the door, Liza launched into the tale of how she came to be a 26-year-old assistant.

When she had finished, Charles did not respond immediately.

Shit. He hates me. I'm fired. Liza tried to keep her cool and not let the panic rising within her bubble to the surface. She stared down at the empty glass in front of her and attempted to slow her heart rate.

But when she looked up at him, she saw not anger, hate, or betrayal in his eyes. There was some confusion, which was understandable, but what shocked her the most was how…relieved he looked.

Her bewilderment must have been plainly laid out on her face because Charles laughed.

"I apologize," he said. "I'm not laughing at you or your story. It's just…if you could see the look on your face. I've heard the phrase 'deer in the headlights' many times, but I'm just getting the full effect of it now."

"You're not…mad?" Liza asked hesitantly.

Charles shook his head. "No, I'm not mad. Still a little confused, but not angry. How could I be?" He hesitated, then put his hand on top of hers. "It's amazing, the things we are willing to do for our kids."

The understanding, the reassurance, the sturdiness of his voice…Liza could have cried in her own relief, but she maintained her composure and let out a relaxed sigh.

"I am curious about one thing, though," he admitted. "How did this work with HR? Your background check, your fingerprinting…there were no red flags."

Liza shrugged. "I didn't lie to them. I didn't think there would be any reason for anyone outside of HR to look at the details of those reports unless something unusual came up. As long as everything cleared, that would be all anyone upstairs needed to know."

The simplicity of that juxtaposed with the complexity of her lie was too much for Charles. He tried to cover up his snickering, but it escalated into a full-blown belly laugh before he could stop himself. Liza couldn't help but join in.

Though their laughs died down, their smiles remained. They sat in contented silence for a moment before Liza spoke again.

"So…" she began, suddenly feeling a little fearful. "What do we do now?"

Charles rubbed his chin thoughtfully. "Well if HR is already aware, that's one big issue we don't have to worry about. I can handle any problems that arise administratively. As for everyone else…I say use your best judgment. I trust that you'll tell them when the time is right."

She smiled warmly at him. "Thank you. For trusting me."

He squeezed her hand reassuringly again. "I know there's no way for me to completely understand what you're going through, but I appreciate and respect the sacrifices you've made—are making—on behalf of your daughter. Being a parent isn't easy, especially when you're doing it alone."

She clasped his hand in hers. "Thank you. And I'm sure you're doing a great job with your girls."

Charles looked intently at the woman seated by him. He couldn't believe the connection the two of them shared after the minimal amount of time they had spent together. Being with her felt exciting and comfortable at the same time, and Charles wanted to stay wrapped in those feelings every day for the rest of his life.

Liza cleared her throat, bringing him out of his reverie. "Um…what do we do about…" she gestured between the two of them, "this?"

Charles felt his heart beating in his throat.

This.

So she was really…interested? She wanted this to go beyond tonight?

"Well…" Charles began, not really sure what he was going to say. "I am your boss. Your boss's boss technically speaking."

Liza nodded. "That's problematic."

"Yes. We have a reporting relationship. Unequal power dynamics can be a big issue in the workplace. I would never want you to feel pressured or uncomfortable."

Liza shook her head. "Me either. And I wouldn't want people to think any success I have in my job is because I'm sleeping with the boss."

Charles's eyes widened a fraction. Sleeping with the boss…

No, he wasn't going to let his mind go there.

Liza caught the change in his facial expression and immediately clapped a hand over her mouth. "I mean not 'sleeping with the boss' like sleeping with the boss. Because we're not. Sleeping together. It's just an expression, you know? I was just sayi—"

Charles put up a hand to silence her. "Don't worry. I know what you meant."

Liza's cheeks were blushing furiously; she almost looked feverish. "So…what do we do?"

"Truthfully I'm not sure what the ins and outs are, but I think the first thing is speaking with HR to disclose our relationship. Besides that…we'll just have to set some professional/personal boundaries and adjust as we go." Charles smiled at her. "I take consolation in the fact that we aren't the first people to have this come up."

Liza returned his smile and nodded. "People meet at work all the time."

Charles looked at her seriously. "If we are really going to do this, please don't hesitate to be honest with me. If you ever feel uneasy or like you're given special treatment…tell me. I will make every effort to maintain whatever boundaries we have in place."

"I will. The same goes for you," Liza agreed. Then she giggled and gave him a coy smirk. "But what about special treatment outside the office?"

Did I really just say that? She was amazed at her boldness this evening.

His cheeks flushed crimson, which made her smile wider.

It captivated him; everything about her did.

I am in trouble, he thought, grinning back at her. "Are you sure you want to do this? We can't go back to how we were after this."

She clasped his hand once more. "I hope not."

Liza saw the joy in face, the affection in his gaze…and she knew she was a little bit in love with him already.