My Worst Enemy Is My Plus One

Episode 1

The engagement party was held in the backyard of her parents’ house, the same wide lawn where Chloe had once skinned both knees learning to ride a bike and where, years later, she had watched her sister fall in love in real time. Tonight the grass was hidden under rented white flooring, string lights hung in careful constellations between the oak trees, and a bar had been set up where the old tire swing used to be. Everything looked expensive and temporary, the way happiness sometimes did when too many people were watching.

Chloe stood near the edge of the light with a glass of something sparkling and too sweet in her hand, smiling the polite, distant smile she had perfected for family events. She had been at the party for forty-seven minutes. In that time she had already been asked about her relationship status by two aunts, one cousin, and a neighbor who used to babysit her. The night was still young.

“Chloe, sweetheart.” Her mother’s voice carried the particular brightness that meant concern was about to be delivered as affection. Patricia Bennett appeared at her elbow in a navy dress that somehow still looked freshly pressed after three hours of hosting. “You’ve been standing over here by yourself. Come sit with us. Aunt Debra was just asking about you.”

Chloe took a slow sip of her drink. “I’m fine here, Mom. Just people-watching.”

“You’re always people-watching. It’s a party. Mingle.” Patricia’s hand settled on her arm, gentle but insistent. “And smile. You look like you’re calculating the fastest exit route.”

She was. The side gate by the garage was only twenty steps away. She had timed it earlier.

Before she could answer, Aunt Debra materialized on her other side, wineglass already half empty, eyes bright with the particular hunger of a relative who had decided someone else’s life was open for public discussion.

“There she is,” Debra said, as if Chloe had been hiding. “We were just saying how lovely Liv looks tonight. Absolute glow. And you—” her gaze flicked over Chloe’s simple black dress, the one she had bought because it required no thought—“you look tired, honey. Work still running you ragged?”

“Something like that.”

“Or maybe it’s the lack of a plus-one.” Debra’s smile was pure sympathy and zero subtlety. “You’re not getting any younger, Chloe. Liv’s settling down, and you’re still… well. Single. It’s not a crime, of course, but it does make a mother worry.”

Patricia made a soft, pained sound of agreement. “We’ve been telling her. A nice young man. Someone steady. Someone who—”

“Mom.” Chloe kept her voice level. “Can we not do this tonight? It’s Liv’s party.”

“I’m only saying it because I love you.” The classic preface. Patricia’s eyes were already shiny with the threat of emotion. “You’re so capable. So smart. I just don’t understand why it hasn’t happened for you yet. Liv found Daniel when she was your age. Earlier, even.”

Chloe’s fingers tightened around the stem of her glass. She could feel the familiar pressure building behind her ribs—the slow, exhausting weight of being the unfinished project in a family that measured success in paired-off units. She had heard versions of this conversation at every holiday, every birthday, every casual Sunday dinner for the last five years. Tonight, under the string lights and the scent of expensive candles, it felt sharper.

She opened her mouth to deliver the usual deflection—work was busy, she was focusing on herself, the right person would come when it was time—when a new voice cut in from behind her.

“Maybe she’s just waiting for someone who can keep up.”

Chloe went still.

She knew that voice. She would have known it in a crowded airport or a silent room or the middle of a natural disaster. Ryan Cole had the kind of voice that carried amusement even when he was saying nothing particularly funny, like the world itself was an inside joke he had already figured out. She turned.

He stood a few feet away in a charcoal button-down with the sleeves rolled to his elbows, one hand in his pocket, the other holding a bottle of beer like it had been placed there by divine right. The string lights caught the sharp line of his jaw and the perpetual almost-smirk that lived at the corner of his mouth. He looked exactly the same as he had the last time she saw him—too tall, too composed, and entirely too pleased with himself.

Madison’s older brother. The permanent thorn in Chloe’s side. The man who had once called her tragic in front of an entire party and somehow still managed to look like the hero of his own story afterward.

His eyes met hers, and the smirk deepened by a fraction.

“Ryan,” Patricia said, brightening immediately. “I didn’t know you were coming.”

“Madison dragged me. Something about moral support and free food.” He took a slow sip of his beer, gaze still locked on Chloe. “Didn’t realize I’d be walking into a diagnostic session.”

Aunt Debra laughed, delighted. “We’re just looking out for our girl. A pretty thing like Chloe shouldn’t be alone.”

“She’s not alone,” Ryan said mildly. “She’s standing right here being interrogated. There’s a difference.”

Chloe felt heat crawl up the back of her neck. She could not tell if he was defending her or simply enjoying the show. With Ryan the two had always been dangerously close.

Patricia waved a dismissive hand. “You know what I mean. A partner. Someone to come home to. Someone to bring to things like this so we don’t have to keep explaining—”

“That she’s single?” Ryan finished. His tone stayed light, but something harder moved underneath it. “I think everyone in a three-block radius has gotten the update by now.”

Chloe shot him a look that should have drawn blood. He only raised an eyebrow, the picture of lazy innocence.

Aunt Debra, undeterred, leaned in. “Do you know anyone, Ryan? A friend from work, maybe? Someone age-appropriate and employed?”

“I’ll take it under advisement,” he said. Then, to Chloe, quieter, “You going to survive the night, Bennett, or should I start planning the extraction?”

“I can handle my own family.”

“Sure you can.” The smirk returned, softer this time, almost private. “You’ve been handling them for years. Look how well that’s going.”

She wanted to throw her drink at him. She also wanted, with a sudden and inconvenient intensity, for him to keep standing exactly where he was so the relatives would have to aim their concern somewhere else.

Patricia was already launching into a story about a coworker’s nephew who was “very successful in finance and just went through a perfectly amicable divorce.” Chloe stopped listening. She stared at the condensation sliding down the side of her glass and counted the seconds until she could reasonably excuse herself.

Ryan shifted closer, close enough that his shoulder nearly brushed hers. The scent of his cologne—something clean and expensive and familiar in a way that irritated her—cut through the candle smoke and the late-summer air.

“They’re not going to stop,” he said under his breath. “You know that, right?”

“I’m aware.”

“So what’s the plan? Keep smiling until you develop an ulcer?”

“My plan is none of your business.”

“Everything about this little circus is my business the second Madison made me put on a collared shirt and show up.” He tipped his bottle toward the cluster of relatives still debating her future. “They’re treating you like a problem to be solved. It’s exhausting just watching it.”

Chloe’s throat tightened. She hated that he could see it so clearly. Hated even more that part of her was grateful someone had finally said it out loud.

“I don’t need your commentary, Cole.”

“You never do. And yet here I am, offering it for free.”

She turned her head and found him already watching her. The party noise—laughter, the clink of glasses, her sister’s bright voice somewhere near the dessert table—faded into a dull roar. For a moment it was just the two of them and the old, familiar static that always lived in the space between.

“Why are you even talking to me?” she asked.

“Because watching you get gently dissected by your own family is less fun than I thought it would be.” He paused. “And because you looked like you were about three seconds from vaulting the fence.”

“I was considering it.”

“I know.” The smirk softened into something that almost looked like concern. “You always were terrible at pretending you were fine.”

Before she could answer, Madison appeared in a swirl of perfume and blonde hair, linking her arm through Chloe’s and shooting her brother a warning look.

“Stop tormenting her,” Madison said. “It’s Liv’s night. Behave.”

“I am behaving,” Ryan replied. “I’m the picture of restraint.”

“You’re the picture of something,” Chloe muttered.

Madison tugged her away before the exchange could escalate, steering her toward the far side of the yard where the quieter guests had gathered. Chloe went willingly. She needed distance—from her mother’s worried eyes, from Aunt Debra’s helpful suggestions, and from the man who had somehow made the entire evening feel sharper just by existing in it.

For the next hour she performed the role expected of her. She congratulated Liv and her fiancé with genuine warmth. She accepted a plate of food she didn’t eat. She laughed at the right moments and nodded when people talked about venues and dress fittings and the impossibility of finding good catering. All the while she felt the weight of being the unmarried sister settle deeper into her bones.

Every so often her gaze drifted across the yard and found Ryan without meaning to. He was easy to track—taller than most of the men, always slightly removed from whatever group he was standing with, as if he were only half participating. Once their eyes met and he lifted his beer in a small, mocking toast. She looked away first.

By the time the toasts began, Chloe had reached her limit. She slipped away during a particularly long speech about love and timing and the beauty of finding your person, cutting through the side gate and into the darker quiet of the driveway. The night air felt cooler here, less crowded with expectation. She leaned against the hood of her car, tipped her head back, and closed her eyes.

Footsteps approached a minute later. She didn’t need to look to know who they belonged to.

“Running away?” Ryan’s voice was low, almost gentle.

“Strategic retreat.”

He came to a stop beside her, close enough that she could feel the heat of him. For a while neither of them spoke. The muffled sounds of the party drifted over the fence—clapping, laughter, someone starting an off-key song.

“They’re not trying to be cruel,” he said eventually.

“I know.”

“Doesn’t make it easier.”

“No.” Chloe opened her eyes and stared up at the dark shape of the oak branches against the sky. “I’m so tired of being the cautionary tale. The one who’s falling behind. Like my entire life is on pause until I produce a boyfriend for inspection.”

Ryan was quiet for a beat. Then: “So produce one.”

She turned her head. He was watching her with that same unreadable expression he had worn in the backyard, the one that always made her feel like he was seeing more than she wanted him to.

“What?”

“A boyfriend,” he said. “Or a reasonable facsimile. Something to get them off your back for a while.”

Chloe let out a short, humorless laugh. “Right. I’ll just order one online. ‘Must be willing to endure Bennett family interrogation and look convincing next to me at a wedding.’”

“Or you could ask someone who already knows the terrain.”

The words hung between them. Chloe stared at him. The string lights from the yard threw faint gold across one side of his face, leaving the other in shadow. He didn’t look like he was joking.

“You’re not serious.”

“I’m rarely serious. But I’m not joking right now.” He shifted, angling his body toward her. “Your sister’s wedding is in six weeks. They’re going to spend every one of those weeks treating your single status like a national emergency. You bring a date—someone who can sell it—and the conversation changes. At least for a while.”

“And you’re volunteering.”

“I’m saying the option exists.”

Chloe’s pulse had picked up without her permission. She studied his face for the usual mockery and found something steadier underneath.

“Why would you do that?”

Ryan’s mouth curved, but the smile didn’t quite reach his eyes. “Maybe I like watching you squirm. Maybe I’m bored. Maybe I think you deserve one weekend where your family talks about something other than your empty ring finger.” He shrugged. “Pick whichever answer makes you least likely to punch me.”

She should have said no immediately. She should have told him he was insane and walked back into the party. Instead she heard herself ask, “What’s the catch?”

“There always is one with you, isn’t there?”

“With you,” she corrected. “There’s always a catch with you.”

He considered her for a long moment. The night pressed in around them, thick with the smell of cut grass and the distant sweetness of dessert wine. When he finally spoke, his voice had dropped into something quieter, almost careful.

“We make it look real. No half measures. No awkward side-hugs and polite distance. If we’re doing this, we sell it hard enough that even Aunt Debra buys it.”

Chloe’s throat felt dry. “That’s a big ask.”

“It’s the only way it works.” He tilted his head. “Unless you’d rather keep smiling through the diagnostic sessions until someone actually schedules an intervention.”

She thought of her mother’s worried eyes. Of Aunt Debra’s helpful suggestions. Of the way every family gathering had started to feel like a referendum on her life choices. She thought of the wedding—six weeks of fittings and dinners and well-meaning relatives asking if she was bringing anyone, and the quiet, crushing weight of having to say no.

And she thought of Ryan Cole, standing in her parents’ driveway like he had every right to rewrite the script of her weekend. It was reckless. It was potentially disastrous. It was the first idea in months that didn’t make her want to disappear.

Chloe looked at him, at the familiar smirk and the unfamiliar seriousness beneath it, and felt something dangerous and hopeful turn over in her chest.

“I’ll think about it,” she said.

Ryan’s eyes warmed, just slightly. “You do that, Bennett.”

He pushed off the car and started back toward the gate. Halfway there he glanced over his shoulder.

“For what it’s worth,” he said, “I was never pretending you were tragic. Not really.”

Then he was gone, swallowed by the light and noise of the party, leaving Chloe alone in the dark with the first real plan she had had in years and the sinking certainty that she was already in trouble.