She agreed to pretend to be his girlfriend—but didn’t expect what happened next

Jenna always thought fake dating was one of those ridiculous movie plots that could never happen in real life. But when Ryan, her older brother’s best friend and the guy she’d shared a mutual love-hate banter with for years, came to her with a proposal, she couldn’t deny how convenient it sounded.

He needed someone to play the role of his girlfriend for the summer. His sister was getting married in August, and his extended family had made his love life their favorite conversation topic. Every family dinner ended with some variation of “When will it be your turn?” or “You’re not getting any younger, Ryan.”

Jenna, on the other hand, had just been ambushed at brunch by her mother and a parade of “eligible men” from church, all of whom were deeply wrong for her. She was tired of being set up, tired of pitiful looks from people who thought single meant incomplete.

Their deal was simple: she’d be his “girlfriend” for three months—attend family events, post a few couple photos, smile for the cameras. In return, she’d get her mother off her back. A mutually beneficial arrangement, with an expiration date: the day after his sister’s honeymoon.

From the very beginning, Ryan set the rules:

1. PDA only when necessary.

2. No actual dating activities outside of family functions.

   
   
   

3. No catching feelings.

Jenna laughed at the last one. “Please. You’re safe from me.”

But pretending with Ryan was dangerously easy. He remembered how she took her coffee without asking. He gave her his jacket when she got cold at an outdoor family BBQ, without making a big deal about it. He’d squeeze her hand under the table whenever his aunt started prying into their “relationship timeline.”

Somewhere along the way, Jenna’s heart started shifting. The “fake” smiles stopped feeling fake. The way he’d look at her when she spoke—like he was actually listening—made her feel seen in a way no one had in a long time.

Still, he gave no sign that anything had changed for him. He was perfectly charming, perfectly detached. Whenever she lingered too long in a moment, he’d break it with a joke or a comment about the next family gathering.

Then came the night of the wedding. The reception was in full swing—twinkling fairy lights, a warm summer breeze, champagne glasses clinking. When a slow song started, Ryan took her hand and led her to the dance floor.

It was supposed to be part of the act. But the way he held her—one hand warm against her back, the other lightly entwined with hers—made her heart race in a way she couldn’t hide. His gaze was steady, unreadable, and for a moment, the rest of the world blurred.

When the song ended, she thought he might kiss her. Instead, he leaned in and whispered, “We should probably end this tonight. Before it gets messy.”

The words hit like a physical blow. She nodded automatically, forcing a smile, and walked off the dance floor before the tears could break free.

All night, she told herself she’d stick to the plan—end it cleanly, avoid making a fool of herself. But the next morning, she couldn’t shake the need to see him. To tell him that for her, it hadn’t been fake anymore.

She showed up at his apartment, heart pounding. She’d barely gotten her words in order when he opened the door—suitcase by his side, jacket in hand.

“I’m moving,” he said quietly. “Out of state. I didn’t tell you because I didn’t want to make this harder.”

Her throat tightened. “When?”

“Today.”

She wanted to ask why. She wanted to tell him everything. But before she could, he gave her a small, tired smile. “You don’t have to say anything, Jenna. We knew this was temporary.”

She turned to leave, because staying there hurt too much. But halfway down the hall, his voice stopped her.

“I was in love with you, you know.”

She froze.

“I didn’t tell you because you never looked at me the way I looked at you,” he said, his voice breaking slightly. “And if we ended it on my terms, I thought maybe… maybe it wouldn’t hurt as much.” He laughed once—short, bitter. “Turns out I was wrong.”

Her eyes burned. “Ryan—”

But he just shook his head, forcing another smile that didn’t reach his eyes. “Take care, Jenna.”

And then he closed the door, leaving her standing in the hallway with the cruelest truth of all—that they hadn’t lost each other because it was fake. They’d lost each other because it had been real for both of them, and neither had been brave enough to say it when it mattered.