Trenton's Date

Trenton sat in the arrivals hall watching the arrivals board. He looked over at the seat next to him, checking on his gas-station bouquet and heart-shaped chocolate box. He checked his DMs just to triple-check that he wasn't hallucinating. Sure enough, she texted him; she said she was coming.

Lena, meanwhile, was kissing her husband Adam goodbye with the casual ease of someone heading out for a quick errand. “I’ll be back tomorrow,” she’d said, grabbing her overnight bag. Adam shrugged, offered a lazy smile, and told her to have fun. Everyone but Trenton knew exactly how this night would end.

She emerged through the sliding doors to the arrivals hall wearing a matching grey sweatsuit and dragging an expensive looking carryon bag. Briefly taken aback by her casualwear (considering he was not only wearing his best shirt for this date, but he'd also ironed it), Trenton rushed up to her excitedly, forgetting his bouquet, and she politely offered him her bag.

“Trenton, right?” she said brightly. “Nice to finally meet you.”

His composure collapsed. He took the bag carefully, briefly, dropped it with a clatter to rush back to his flowers and chocolates and rushed back and picked it back up. She smiled on politely.

She looked even better in person — confident, radiant, and way too put-together for the likes of him.

He thrust the sad bouquet toward her. “These are for you.”

“Aw, thank you. That’s really sweet.” She accepted them with genuine politeness and followed him out to his car. She couldn't help but notice the missing hubcap and, as he opened the door for her, the faint smell of McDonalds that no air freshener could fix. She slid in with the same upbeat energy, chatting lightly about the flight, making smalltalk to expertly soothe the nervous twenty-one-year-old currently gripping the wheel with sweaty hands.

Every time he glanced over at her — at the way the sweatsuit hugged her figure, at how effortlessly gorgeous she was in her casual clothes — a fresh wave of starstruck awe rolled through him. There was no doubting the coin now. She, the Lena, was really here. Sitting in his car. He just had to not screw this up.

On the drive to dinner, Trenton decided to shoot his shot early. He reached across the center console with what he imagined was smooth confidence, aiming to take her hand like they did in the movies. Lena let his fingers brush hers for half a second before gently pulling away with a soft, amused laugh.

“That’s sweet, Trenton, but I’m a married woman, remember?” she said kindly, as if reminding a puppy not to jump on the furniture.

His cheeks burned, being turned down this way by someone who films herself sleeping with strangers every day, but he **** a chuckle and kept his eyes on the road. It’s fine, he told himself. The bet only said a date. She’s still here. The awe hadn’t faded — if anything, hearing her say his name in that warm, real voice made his stomach flip again.

He pulled into the Olive Garden parking lot with the triumphant air of a man who had just delivered his date to the fanciest restaurant in the tri-state area. “Best Italian in town,” he announced proudly, as if the glowing neon sign and strip-mall surroundings were part of the romance package.

"Yeah.. I love breadsticks," she smiled up at him.

Inside, Trenton had gone all out: he’d requested a “romantic” corner booth. When they sat down, the single tea-light flickered between them like a sad, lonely firefly. Trenton leaned forward, trying to sound smooth. “You look incredible in that top, by the way. Like… seriously. It really shows off your—”

“Thank you,” Lena cut in smoothly, her smile never wavering. “That’s very kind, Trenton.” She immediately steered him back to smalltalk, what he did for work. The candle felt increasingly ridiculous as the breadsticks arrived and she broke one in half with elegant fingers, completely unbothered.

Trenton tried again during the main course. He “accidentally” let his leg brush against hers under the table while ordering the Tour of Italy combo. When she deflected, he doubled down and suggested they share a big chocolate brownie dessert “so we can feed each other, you know… for fun.”

Lena gave a light laugh. “I’m actually pretty full already. But you go ahead if you want.” She stayed perfectly nice, chatting and laughing at his stories, but no more intimate than a big sister humoring her little brother’s crush. His haert finally came to sink in his chest with the realization of how his dream night would go.

The bet had brought her here, sure — but it hadn’t made her want any of this.

By the time they reached the cinema, his earlier hype had cooled into something quieter and more deflated. She was still here, still smiling, still breathtaking even in her casual clothes — and he was still completely in awe of her. But every gentle rejection was starting to stack up, reminding him exactly how Emily had worded her bet. He wondered if she had done this on purpose.

By the time the credits rolled and they stepped back into the chilly night air, Trenton was noticeably quieter. He noticed her shivering and quickly put his jacket around her shoulders. She did appreciate that, even if it smelled like his cheap aftershave.

They pulled up to his modest one-bedroom apartment a little after midnight. He dragged her bag into the room behind her. “So… this is my place,” he said, rubbing the back of his neck. “I already changed the sheets and ... everything.”

She looked at him curiously. "That's lovely..."

Lena looked around the small living room, taking in the gaming setup, the scattered sneakers by the door, and the single sad houseplant he’d forgotten to water. She smiled kindly.

He tried one final, half-hearted try as she set her bag down, knowing he'd kick himself for not trying one last time. “Would you like to cuddle a little? The bed’s big enough for both of us.”

She gave him the same warm, patient smile she’d been using all evening — the same smile that gave him hope and shot it down at the same time. “You can take the sofa. Seriously, thank you again for being such a gentleman tonight.”

Lena disappeared into the bathroom to change. When she came out in simple silk pajamas that still managed to look more expensive than his car, she climbed straight into his bed without hesitation and reached for her phone to text Adam.

Trenton’s throat tightened. He couldn’t stop staring. There she was — Lena, the Lena — lying in his bed like she belonged there, her hair fanned across his pillow, the faint scent of her perfume already mixing with the laundry detergent he’d used. She looked peaceful. Radiant. Completely at ease.

And he was… here.

His stomach sank further. Part of him wanted to laugh. The awe that had carried him through the entire night was still there, but now it felt poisoned with something sharper — humiliation, heavy and hot, pressing down on his ribs. She had been so fucking nice to him all evening. That was almost the worst part. Every polite smile, every gentle redirection, every “that’s sweet, Trenton” had kept that fragile hope alive just enough to make the final drop hurt more.

He finally turned away, grabbed his pillow and the old blanket from the closet, and shuffled to the couch. The springs creaked loudly as he lay down, the fabric rough against his skin. From the bedroom he could hear the faint tapping of her fingers on the screen, then silence.

Long after the apartment lights were out, Trenton lay awake, eyes wide open in the dark. Every time he closed them, he saw her smile again — that warm, patient, untouchable smile. The same one she probably gave hundreds of fans who dreamed bigger than they should.

It was still by far the best day of his life, but he was just a couple of words (with that damn coin) from his dream. It was hard not to be mad at Emily for taking this away from him...