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First Date with Gregory

Summary:

Mycroft is antsy. He's at the office. Tonight is his first date with Gregory and his nerves are getting the better of him. His nerves don't get any better when he goes home either.

Chapter Text

Mycroft fidgets restlessly at his immaculately organized desk, an anomaly in his character that rarely surfaces. Anthea’s sharp eyes catch the slight tremor in his hand as he shuffles papers and adjusts his pen. “Sir, are you all right? You seem rather out of sorts,” she inquires, her tone laced with genuine concern.

 

A heavy sigh escapes him as he admits, “Detective Inspector Lestrade asked me out on a date, and I said yes. Now, all I feel is a chaotic flutter in my chest. The date is tonight, and my anxiety has soared through the roof. What was I thinking?” His tone is grave, laced with uncertainty.

 

Her smile is both encouraging and teasing. “Well done, sir. Bravo, indeed. Detective Inspector Lestrade is a lovely man—there’s nothing to fear. You know him, and he chose you for a reason. Set your doubts aside tonight—ignore the calorie count. Tell me, where is he taking you?”

 

He exhales heavily. “He mentioned an upscale Italian restaurant, though he wouldn’t divulge the name.”

 

“Then that must be an opportunity to savor every course,” she chimes in, her tone playful and vivid. “Start with a tantalizing appetizer, enjoy a lavish entrée, indulge in dessert, and don’t hold back on the wine. Tonight, let yourself delight in the experience. The Inspector is delightful company, and if I’m not mistaken, his humor will make the evening truly remarkable. How long do you have to remain here before you can head home?"

 

“Only another half hour,” he responds, eyes flicking to the clock. “Why do you ask?”

 

“Good,” she declares with a teasing smile. “Because you’re driving me up the wall, and if you tap those fingers on that desk one more time, I might just tape your hands in place!”

 

“My apologies, Anthea,” He murmurs, his voice tinged with exasperation. “I know I’m not doing myself any favors by allowing my nerves to take over. Perhaps you might advise me on what to wear?”

 

“A blue suit would be perfect—ditch the waistcoat and pair it with a light blue shirt. It will accentuate your stunning blue eyes, which, if I may add, are one of your finest features. And do remember, smile often and let out as much laughter as you can; the detective appreciates a good sense of humor. You’re bound to have a splendid evening.”

 

A faint blush colours his cheeks as he murmurs, “I certainly hope so. He is truly a wonderful man.”

 

“Ah, someone clearly has a crush! And he is undeniably handsome,” she prods gently, urging him to reveal more about his thoughts on Greg. “Tell me, don’t you think he’s absolutely dashing? Not to mention in impeccable shape.”

 

Despite his efforts to hide it, his voice softens, his admiration slipping out almost inaudibly, “God, he really is handsome, isn’t he? And in such fine shape too.” He groans, embarrassed by his own candor; he trusts her implicitly, knowing that even if others, Sherlock especially, might use his vulnerability against him, she will not.

 

“Now, you must go home, sir. I promise not to reveal that you managed an early departure for once,” she encourages warmly.

 

But he hesitates, fidgeting with his overcoat and umbrella. “If I go home now, what will I do? Gregory isn’t joining me until 7:00. I’d be left alone with my spiraling thoughts in that empty house until then.”

 

“Perhaps you could watch some television, lose yourself in a good book, plan your outfit carefully, and maybe even enjoy a stiff drink to soothe your nerves. You can absolutely do this. I have every confidence that the Inspector will make your evening as comfortable and engaging as possible. He’s an incredibly warm-hearted man, and tonight will unfold naturally. Just be open with him—if you build too many walls, he might retreat behind his own. Just be your true self. It’s been plain as day for quite some time now that he is fond of you.”

 

“Really? How long have you known that Gregory likes me?” he asks, his tone mixed with curiosity and a timid excitement.

 

Anthea leaned in conspiratorially. “Sherlock mentioned it over two years ago—long before this date was even a thought. He once even tried to persuade me to set you both up, but I insisted on letting things develop naturally. I’ve watched you two exchange flirtatious glances for years now. Just promise me—no snogging in the office or in the car when I’m present!”

 

“Let’s see how this first date unfolds before we get too carried away with future visions,” he replies, a blush deepening on his cheeks as he imagines the prospect of Gregory’s kiss—a thought he has secretly entertained while discreetly admiring his date's lips during their many shared moments as friends up until this point.

 

“Now, please go home, sir. Your mind is adrift in the clouds right now, making you rather unfit for duty,” she says with a gentle pat on his shoulder.

 

Taking a deep breath, he gathers his overcoat and umbrella with deliberate care. “Thank you for your invaluable advice, Anthea—it was much needed. It has been far too long since I ventured on a date, and my nerves are understandably frayed.”

 

She teases gently, “Since I’ve been working for you, you haven’t been on a date at all. But honestly, it doesn’t matter if you’re a bit out of practice—the Inspector is likely to be just as inexperienced in dating after such a long hiatus after his marriage and then his divorce.”

 

“That’s rather reassuring,” he admits, a touch of humor in his softened tone. “After all, Gregory was married for fifteen years and has been divorced for two, meaning he’s been out of the dating scene just as long as I have. That makes this slightly more equal, and somehow that comforts me. I’ll see you tomorrow, Anthea.” With that, he presses a gentle kiss to her cheek and leaves his office behind, stepping into the night with a mix of trepidation and hopeful anticipation.

 

 

Chapter 2: Going Home Early

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“Good night, Mr. Holmes. It’s a rare occasion to see you depart on time,” Richard, the ever-attentive receptionist for the building, remarks with a hint of amusement as he observes Mycroft making his way towards the exit.

 

"I have a date tonight and I’m keen not to be late. It's considered very bad form, you know," Mycroft replies with a warm smile, his eyes gleaming with anticipation. "Have a good night, Richard."

 

“Good night, Mr. Holmes. Enjoy your evening,” Richard responds, a knowing twinkle in his eye as Mycroft steps out into the cool night air.

 

"I'm sure I will." Mycroft exits the building, his polished shoes clicking softly against the pavement. He glides into the discreet black sedan, a vehicle as understated and enigmatic as its owner. Settling into the plush leather seat, he leans his head back against the headrest, feeling the coolness of the material against his skin. A flicker of nerves dances through him, yet there's a curious comfort in knowing that Gregory, too, will find himself out of practice. The thought eases some of the tension in his shoulders, allowing him a moment's respite as the car purrs softly to life.

 

“Are you all right, Mr. Holmes?” Mycroft’s driver, Simon, inquires with a gentle tone, his eyes briefly meeting Mycroft’s in the rearview mirror.

 

“Yes, I’m fine, thank you, Simon. My nerves are simply getting the better of me. I’m going on a date tonight,” Mycroft replies, a hint of anxiety lacing his words as he gazes out the window at the passing scenery.

 

“Good for you, sir. Is he anyone I know?” Simon asks with a playful, cheeky grin, his curiosity piqued.

 

“Detective Inspector Lestrade asked me out a few days ago, and we decided to go out to dinner tonight,” Mycroft shares, a hint of warmth creeping into his otherwise composed demeanor.

 

“Well done, sir. The detective is a lovely man. Good choice, sir,” Simon responds with genuine approval, nodding slightly as he keeps his focus on the road.

 

“I think so too. I hope I still think it was a good choice at the end of the night,” Mycroft says heavily, a shadow of doubt creeping into his voice as he fiddles with the cuff of his shirt.

 

“I think you’ll be fine, sir. If I can give you one piece of advice: don’t overdrink. It makes the whole evening awkward,” Simon advises sincerely, his voice carrying a touch of wisdom born from experience.

 

“I never overdrink. It never ends well. I’m a terrible person when I’m drunk, and I never want Gregory to see that side of me,” Mycroft admits, running a hand wearily over his face, his expression thoughtful and introspective.

 

Sensing his boss's need for contemplation, Simon decides to let the conversation lapse into silence, allowing Mycroft the space to gather his thoughts. In the back seat, Mycroft finds solace in the quiet, a rare stillness settling over him like a comforting blanket.

 

Simon maneuvers the car with smooth precision, bringing it to a gentle halt in front of Mycroft's stately house. "Have a good night, sir," Simon says, opening the car door with a courteous flourish.

 

“Thank you, Simon. Can you pick me up at 6:30? We have a reservation at 7:00,” Mycroft requests, stepping out of the car with a composed elegance.

 

“Of course, Mr. Holmes. I’ll see you later,” Simon replies with a reassuring smile, watching as Mycroft strides towards the front door, the promise of the evening ahead lighting a spark of anticipation in his step.

 

 

 

Chapter 3: Getting Ready

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Mycroft ascends the stairs to his elegantly appointed townhouse, unlocking the door with a sense of relief. The prospect of a soothing shower, a meticulous shave, and a perfectly brewed cup of tea beckons him. He places his sleek leather briefcase in his tastefully arranged home office and bounds up the staircase with renewed energy. Now that he has left behind the sterile confines of his office, his nerves begin to unwind, feeling less like iron chains and more like manageable threads. Shedding the constraints of his tailored work suit, he tosses the crisp dress shirt and vest into the laundry basket with a sense of liberation. Sliding into the comfort of his plush dressing gown, he makes his way to the bathroom, one of his sanctuary-like favorite rooms in the house. The bathroom is a masterpiece of design, boasting polished marble surfaces and gleaming fixtures. He turns the shower's tap, releasing a cascade of hot water, and places a luxuriously fluffy, white towel on the heated towel rack, anticipating its warmth. With deliberate care, Mycroft slips the gleaming gold ring from his right hand’s ring finger, setting it gently on the cool countertop. Hanging his dressing gown on the back of the door, he steps into the inviting embrace of the shower stall. The water is a comforting heat, working its magic to untangle the knots and ease the tension from his muscles. He reaches for his favorite body wash, its fragrance a delicate whisper that won't overpower the cologne he plans to wear later.

As the water ceases its flow, he reaches for the towel, its warmth enveloping him in a cozy embrace as he dries off, securing it snugly at his waist. The mirror is a hazy blur of steam, which he clears with a swipe of his hand, revealing his reflection. Carefully, he shaves away the day’s accumulation of stubble with precision; razor burn is not an accessory he wishes to sport for his evening engagement.

He slips the gold ring back onto his finger, regarding his reflection thoughtfully. The ring, a silent testament to something personal, is best left unexplained, though he trusts Gregory won’t pry into its meaning. Content with his appearance, he leaves the ring in place, a quiet emblem of his own untold story.

The next task on his agenda is to select the perfect outfit for his date. His wardrobe boasts an array of blue suits, each finely tailored and exuding a unique charm. After some deliberation, he opts for the one with delicate pale blue pinstripes that harmonize beautifully with the crisp shirt he has already chosen. Accessories are next on the list, and he recalls Anthea's advice to forgo the waistcoat, steering his focus to selecting the right cufflinks and watch. His extensive collection of cufflinks glints under the light, each pair a testament to his meticulous taste. After a contemplative selection process, he picks a pair of elegant silver cufflinks adorned with a striking blue stone, complemented by a sleek silver watch with a matching blue face. He lays everything out meticulously on the bed, admiring the ensemble before retreating to the window seat with a book in hand.

This rare pocket of free time feels like a luxury, and he relishes the opportunity to unwind a bit before his evening begins. The book, which has been languishing on his nightstand, beckons him to resume a journey he can barely recall. As he reads, he remains vigilant of the ticking clock, determined not to let time slip away and make him late. By 6:05, he reluctantly sets the book aside and begins to dress with care. The suit and shirt fit him like a glove, the cufflinks are fastened with precision, and the watch slides smoothly beneath the cuff of his dress shirt. He dons the suit jacket with deliberate gentleness, ensuring no creases mar the fabric's pristine surface. A quick visit to the bathroom has him applying a dash of cologne, its scent adding a final touch of sophistication. He steps into his polished shoes, feeling the anticipation build.

Anthea had playfully suggested a stiff drink before Gregory’s arrival, but he decides against it, preferring to remain clear-headed for the evening’s dinner. As he reaches the bottom of the stairs, the doorbell’s chime resonates through the house. Taking a deep breath, he opens the front door to find Gregory standing there, a smile lighting his face. “Hello Gregory.”

“Hi Mycroft. You look very nice,” He remarks warmly as he steps into the grand foyer, wrapping him in a friendly embrace. The space is filled with soft lighting, casting a gentle glow on the polished marble floors.

“You look very elegant, Gregory,” he replies, returning the embrace and then leaning in to plant a tender kiss on his cheek as he pulls away, a subtle scent of cologne lingering in the air.

“Are you ready to go to dinner?” He asks with a broad, inviting smile that lights up his face.

“Absolutely. Do I need my coat?” He inquires, turning towards the ornate closet door, its mahogany wood gleaming in the light.

“It’s up to you. We’re only going from here to the car and then the car to the restaurant. I’ll keep you warm if you get cold,” He assures him, his voice carrying a playful undertone.

He blushes, a hint of pink coloring his cheeks, understanding the sweet implication behind his words. He finds the idea delightful and closes the closet door with a soft click. “Let’s go then,” he says with a small, pleased smile.

“Can I ask you something?” He pauses, his hand resting on the intricately carved door handle.

“Of course you can. What is it?” He asks gently, his voice full of curiosity.

“Do you mind if I hold your hand?” He asks earnestly, his gaze sincere and hopeful.

“No, of course not. I would like it very much, actually,” he admits, a soft smile gracing his lips, as he reaches out, intertwining his fingers with Greg’s.

Chapter 4: Heading to the Restaurant

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As they step out of Mycroft’s stately Kensington townhouse, they glide into the luxurious, black government car waiting at the curb. The vehicle, with its polished exterior gleaming under the streetlights, pulls away with effortless grace, merging seamlessly into the flow of evening traffic as it heads towards the restaurant. "I have to admit that I'm nervous," Greg confides, a hint of apprehension lacing their words.

"So am I," Mycroft replies with determination, a firm resolve etched into his expression, "but I am not going to let it overwhelm me." His voice carries a calm certainty, as if he's drawing a line in the sand against the chaos. He shifts the conversation with a deliberate ease, asking, "So, where are we going for dinner?" His words hang in the air, offering a welcome diversion, as if the anticipation of a warm meal could momentarily dissolve the weight of their worries.

"I know this charming little Italian restaurant, a hidden gem that exudes an authentic, upscale vibe. It's the place where I gather with my parents every year to celebrate my birthday. With its intimate, cozy atmosphere and unassuming exterior, it feels like a secret tucked away from the bustling city. I think you'll appreciate its warmth and charm."

"That sounds absolutely perfect. I have a deep appreciation for good Italian food and wine, with their rich flavors and comforting aromas. Unfortunately, I seldom get the opportunity to truly savor a meal as one should, allowing each bite to linger on the palate and every sip of wine to unfold its complex notes."

"Well, you have a chance tonight. They've secured a perfect corner table for me, tucked away with just the right amount of privacy. It’s been quite some time since I last visited, and I’m eagerly anticipating the experience. Their soup is truly exceptional, a rich blend of flavors that warms the soul with every spoonful."

"You seem quite excited," he teases gently, his voice carrying a warm undertone. He watches Gregory with a fondness in his eyes, appreciating the rare sight of his usually composed friend so free and relaxed. Gregory's eyes are alight with enthusiasm, a genuine smile playing on his lips, and his whole demeanor radiates an infectious energy. It's a moment Mycroft treasures, seeing the Gregory unwind and let his guard down.

"I am thrilled! I’m taking you on a special date to my favourite restaurant, a cozy little spot with warm, ambient lighting and the rich aroma of spices wafting through the air. Perhaps this charming eatery, with its inviting atmosphere and mouthwatering dishes, will become our special place."

"I've never had a place with another person before," he admits, his voice barely above a whisper, as if speaking the words too loudly might shatter the delicate moment. He becomes acutely aware that their hands are still intertwined, their fingers gently clasped together. The warmth of the other person's skin against his own is unexpectedly comforting, a simple connection that feels both unfamiliar and profoundly right. He finds himself savouring this newfound intimacy, a soft smile playing on his lips as he realizes just how much he likes it.

"Really? That's kind of sad," he muses, his voice tinged with a hint of melancholy. "But, you know, whether or not this becomes our special corner of the world, we will have a place. We will find our own nook, a sanctuary where we belong."

"That's very sweet, Gregory," he says softly, leaning over to plant a gentle kiss on his cheek. The warmth of the gesture lingers in the air, mingling with the soft hum of the car engine.

"Can I ask you something?" Greg inquires, his tone suddenly serious. Mycroft nods, turning slightly on the plush car seat to face him, the soft leather creaking beneath him. "When did you know that you liked men?" Greg's voice holds a quiet curiosity.

"I've always known," he replies thoughtfully, his gaze distant for a moment as he reflects. "I struggled with telling others that I was gay, but I think that's a common challenge. Internally, I've never had an issue with being gay. It didn't really change much at school either, except it made me stand out more, like more of a freak." He pauses, then redirects gently, "What about you? When did you discover or admit that you were bisexual?"

He takes a deep breath, the memory seeming to weigh on him. "I didn’t admit it to myself until I went off to uni," he confesses, his eyes momentarily distant. "But I knew that I was bisexual by the time I was fifteen." He pauses, the car's engine humming quietly around them.

"Well..." He starts, searching for the right words, but before he can continue, the car comes to a smooth stop in front of the elegantly lit restaurant, saving him from the need to respond immediately.