Seen you before?
Patrick Dempsey x Reader/ First encounter • SFW
Main Masterlist | Patrick Dempsey Masterlist | Dr. Derek Shepherd Masterlist | Angelo Doyle Masterlist
A/N: The monaco interviews got me going 🙈
Warnings: age gap, soft flirting, fresh-divorce emotions, mild alcohol mention, romantic tension, no explicit smut.
The first mistake you made was downloading Raya.
The second was opening it at one in the morning after two glasses of wine and a long travel day.
And the third—easily the worst—was accidentally swiping right on Patrick Dempsey.
You froze the second his profile appeared on your screen.
It was simple. Almost annoyingly normal. A black-and-white photo, another one at a racetrack in racing gear, one with a coffee mug and his dog. His bio only said: Actor. Racing. Coffee. Trying to figure life out.
You stared at the screen for a solid thirty seconds before muttering, “Absolutely not.”
Because this was Patrick Dempsey. McDreamy. Your teenage obsession. The reason fourteen-year-old you thought emotionally unavailable men with pretty eyes were romantic.
There was no universe where Patrick Dempsey would ever swipe right on you.
Sure, you were successful. You had built a solid reputation as a journalist and interviewer. You attended film festivals, sports events, fashion launches and award ceremonies for work. But Patrick Dempsey still belonged to that category of celebrity that didn’t quite feel real.
You meant to swipe left.
Instead, your thumb slipped.
The screen flashed instantly.
It’s a match.
Your entire body went still.
“Oh my God.”
You stared at your phone in genuine horror before dropping it face-first onto the bed like it had personally betrayed you. For the next ten minutes you seriously considered deleting the app entirely out of embarrassment.
Eventually, you convinced yourself to calm down. It didn’t matter. Men like Patrick Dempsey probably matched with hundreds of people. He likely wouldn’t even notice your profile among the endless stream of actresses, models and influencers flooding the app.
By morning, you had almost managed to forget about it.
Almost.
Monaco during Grand Prix weekend was complete madness. The entire city buzzed with expensive energy—luxury cars crawling through narrow streets, yachts crowding the harbor, celebrities moving in packs while photographers hovered nearby hoping for one good shot.
You were halfway through your second coffee during the media briefing when your editor handed over the updated celebrity interview schedule.
You skimmed through the names lazily until your eyes landed on one entry.
Patrick Dempsey.
Your stomach dropped so fast it was almost embarrassing.
“Oh, you’ve got him around five,” your editor said casually while checking her phone. “Apparently he’s lovely. Should be an easy interview.”
Lovely.
That somehow made things worse.
The entire afternoon became a blur after that. Back in your hotel suite, clothes were scattered everywhere while you tried to decide what counted as “professional but effortless” without looking like you had clearly overthought the outfit.
You eventually settled on an ivory satin blouse tucked into black tailored trousers with minimal jewelry and soft makeup. Clean. Elegant. Safe.
Definitely not chosen because Patrick Dempsey might look at you.
By the time you arrived at the VIP hospitality area near the paddock, the atmosphere was already electric. Music drifted through the open terraces overlooking the marina while waiters moved around carrying champagne trays. The air smelled faintly of sunscreen, expensive perfume and overheated engines.
Your earlier interviews went smoothly enough. Years in journalism had trained you to stay calm around famous people. You could interview Oscar winners and athletes without blinking.
But the second a producer leaned over and quietly said, “Patrick’s ready for you,” every ounce of composure threatened to disappear.
You turned toward the interview setup and immediately understood why the internet lost its mind over that man.
Black suit. White shirt slightly open at the collar. Sunglasses hooked loosely into one hand. The late afternoon Monaco sunlight caught the silver threaded through his hair and suddenly he looked less like an actor and more like someone designed in a laboratory to make women nervous.
As you approached him, your heel caught slightly against the flooring.
Not enough to fully stumble.
But enough.
Before you could properly recover, Patrick instinctively reached out and steadied your arm lightly. “You okay there?” he asked, smiling in a way that felt unfairly warm.
You let out a breathy laugh, immediately embarrassed. “Yeah. Totally fine. Just trying to make a memorable first impression.”
That made him laugh softly. “Well now I feel better because I was nervous too.”
You blinked at him. “You were nervous?”
“A little,” he admitted easily. “You’re the journalist. You ask the scary questions.”
Something about the way he said it instantly relaxed you.
The cameras started rolling a moment later and somehow the interview flowed naturally almost immediately. Patrick was surprisingly easy to talk to. He didn’t give polished media-trained answers or try too hard to sound charming. If anything, he seemed more comfortable discussing racing than acting.
The second the conversation shifted toward endurance driving and Le Mans, his entire face lit up. “There’s something really grounding about racing,” he explained thoughtfully. “When you’re driving, nothing else exists for a while. You can’t think about life or stress or anything outside the car because if you do, you lose focus.”
You nodded. “That actually sounds therapeutic.”
“It is,” he said with a small smile. “Probably cheaper than therapy too.”
At one point you admitted that your only fast-driving experience ended with you nearly crying in the passenger seat during a Ferrari experience in Dubai. Patrick laughed so hard he leaned forward slightly in his chair.
“That bad?”
“I genuinely saw my ancestors,” you deadpanned. “The driver kept yelling ‘isn’t this fun?’ while I was preparing to meet God.”
He laughed properly then—not the polite celebrity laugh people fake during interviews, but a real one that crinkled the corners of his eyes.
And after that, the conversation became easy.
Really easy.
You spoke about travel, Monaco, race weekends, jet lag and how strange it was constantly living out of hotel rooms. Patrick listened carefully when you spoke instead of just waiting for his turn to answer, which felt surprisingly rare.
When the interview wrapped, he thanked every crew member individually before standing up.
“That was fun,” he said sincerely while unclipping his mic.
“It was,” you admitted.
“You made it easy.”
And annoyingly enough, that small sentence stayed with you long after he walked away.
By evening, Monaco transformed completely. The sporty daytime energy melted into glamour as terraces filled with celebrities, executives and drivers dressed in black tie while music echoed through the harbor.
After finishing your final segment for the night, you escaped outside onto one of the quieter balconies attached to the hotel ballroom. You needed a moment away from people, cameras and conversations.
The sea breeze cooled your skin instantly as you leaned against the railing with a champagne flute in hand, staring out at the yachts below.
For the first time all day, you finally relaxed.
“You disappeared.”
The familiar voice behind you made your stomach flip immediately.
You turned and found Patrick standing there with his suit jacket gone and his sleeves rolled slightly to his forearms. His tie had disappeared somewhere too, leaving the top few buttons of his shirt undone in a way that should not have been attractive but unfortunately was.
“Oh,” you said intelligently.
He smiled. “Mind if I join you?”
“Not at all.”
Patrick stepped beside you at the railing, glancing briefly toward the water before looking back at you. Up close without cameras around, he seemed calmer somehow. Less polished. More real.
For a few seconds, neither of you spoke.
Then he smiled slightly and said, “You seem less nervous now.”
You let out a soft laugh. “Was it that obvious?”
“A little.”
“That’s deeply embarrassing.”
“No, it was actually kind of flattering.”
You looked at him suspiciously. “Why?"
“Because I don’t think people usually get nervous around me anymore.”
You stared at him for a second before laughing softly. “Patrick, you were literally everyone’s crush.”
“That sounds dangerous.”
“It was. Grey’s Anatomy permanently damaged an entire generation of women.”
That made him grin. “And you?”
You took a sip of champagne before answering honestly. “Unfortunately, yes.”
His smile widened slowly, clearly amused by your embarrassment now. “So that’s why you almost tripped earlier.”
“Oh my God.”
“I’m putting the pieces together.”
“You’re enjoying this way too much.”
“A little,” he admitted.
The conversation drifted naturally after that. You talked about travel schedules, the strange loneliness of constantly being surrounded by people and how events like Monaco could feel glamorous and exhausting at the same time.
At one point Patrick leaned against the railing beside you and said quietly, “People think these events are exciting every second of the day, but honestly sometimes they feel strangely lonely.”
Something about the honesty in his voice caught your attention.
“You seem good at hiding it,” you admitted softly.
“That’s part of the job.”
The answer sat quietly between you for a moment.
Without cameras and interviews around him, Patrick felt unexpectedly grounded. Warm. Funny in a very natural way. There was no performance to him.
And somehow that made him even more attractive.
A breeze lifted a few strands of your hair across your face and before you could move them yourself, Patrick reached over instinctively and tucked them gently behind your ear.
The movement was small.
Careless almost.
But the second his fingers brushed your skin, the atmosphere shifted.
Neither of you moved immediately afterward.
Patrick looked at you for a second longer than necessary before suddenly exhaling a small laugh under his breath.
“What?” you asked quietly.
He rubbed the back of his neck slightly, almost sheepish now. “Okay, this is either going to sound smooth or incredibly embarrassing.”
“That’s already a bad start.”
He laughed softly. “I know you from somewhere else.”
Your stomach dropped instantly.
Patrick noticed your expression immediately and smiled. “Not in a creepy way, I swear.”
“Oh this keeps getting worse.”
“I saw you on Raya.”
Heat rushed straight to your face so fast it physically hurt.
“Oh my God.”
“There it is,” he said, laughing now. “That reaction confirms it.”
You covered your face briefly with one hand. “Can we pretend this conversation never happened?”
“No,” he said immediately. “Absolutely not.”
You groaned. “I didn’t even mean to swipe right on you.”
His eyebrows lifted. “Wow.”
“No wait—that sounds horrible.”
“It really does.”
“You were my childhood crush! I panicked.”
That made him laugh again, softer this time. “Okay, fair.”
“I almost deleted the app afterward.”
“Good,” he replied easily. “I’m glad it wasn’t just me.”
You looked at him properly then. “Wait… you noticed?”
Patrick leaned slightly against the railing beside you, smiling almost shyly now. “Pretty hard not to notice the journalist I interviewed with six hours later.”
Your stomach flipped violently.
Then after a small pause, he asked quietly, “So it wasn’t an accident?”
The teasing was still there, but softer now. More genuine.
You met his eyes for a second before admitting, “No. Not really.”
Something warm shifted across his expression.
“I’m glad,” he said simply.
The silence afterward didn’t feel awkward.
If anything, it felt comfortable.
Easy.
Hours passed without either of you noticing. The party continued loudly behind you while the two of you stayed tucked away near the balcony railing talking about everything and absolutely nothing.
And somewhere between the champagne, the Monaco lights and Patrick Dempsey smiling at you like you were the only person in the room, he stopped feeling like a celebrity entirely.
He just felt like a man you genuinely liked being around.
Eventually someone from inside called his name and Patrick glanced back reluctantly before looking at you again.
“You busy tomorrow after qualifying?”
Your heart skipped instantly. “I have interviews until four.”
“I can work with four.”
You smiled despite yourself. “Are you asking me on a date?”
“In Monaco?” he said with a grin. “Feels appropriately dramatic.”
You laughed softly before nodding.
“Okay.”
And the smile Patrick gave you afterward stayed with you long after the night ended.