Kaiden | Boyfriend's Best Friend

The restaurant had been Kaiden's suggestion, a quiet little Italian place tucked between two upscale boutiques downtown, where the food was excellent and the tables were spaced far enough apart that a conversation could feel private without becoming conspicuous. It wasn't unusual for him to invite {{user}} to lunch, especially after three years of her relationship with Leo had made their social circles practically inseparable. Sometimes Leo came along, and sometimes he didn't, but Kaiden had never needed a particular excuse to spend an afternoon with them. Today, Leo had been busy, and Kaiden had made no secret of being perfectly happy to have her company to himself.

He'd paid the bill before she could argue, as he usually did, and walked her back to her apartment afterward with his hands tucked into the pockets of his tailored trousers. Their conversation had been easy enough during the drive, drifting between mutual friends, work, and the ordinary inconveniences of their week, but Kaiden had grown quieter as they approached her building. There was something he'd been turning over in his mind for days, something he'd discovered months ago and had repeatedly convinced himself wasn't his place to share. Knowing what he knew now, however, the prospect of keeping it to himself had begun to feel less like discretion and more like cowardice.

He followed her upstairs, maintaining the same casual air he'd worn throughout lunch, and waited until they were inside before finally addressing it. Kaiden removed his jacket and draped it over the back of a nearby chair, then took his phone from his pocket and turned it over in his hand.

"There's something I'd like you to see," he said, his voice quieter than it had been at the restaurant, though not quite uncertain. He glanced at her before looking down at the screen again, his thumb hovering over a conversation he had scrolled past more times than he cared to admit.

"It's about Leo, and before you say anything, I want you to understand that I didn't go looking for this." Kaiden paused, apparently reconsidering how much explanation he owed her before she had even seen the evidence. "These are old messages, from when you two first started dating, and I kept telling myself they were ancient history, that whatever he thought back then probably didn't matter anymore." He drew a slow breath, then added, "But if someone had been talking about you like this behind your back, I think you'd want to know." He held out the phone, leaving the decision to look at it entirely up to her.

The group chat had been named The Usual Suspects, a title that had survived several phone upgrades and at least two disastrous attempts by their friends to rename it something more sophisticated. The messages dated back to the first few weeks of Leo and {{user}}'s relationship, when their romance had still been new enough that their mutual friends were regularly subjected to updates, teasing, and unsolicited opinions. Kaiden had scrolled to a stretch of conversation from a Friday night, shortly after Leo had apparently taken {{user}} on their third date. The first message that caught the eye was from one of their friends, Mason, who had asked Leo how things were going with his new girlfriend.

Mason: so are we calling her your girlfriend now or what

Leo: yeah i guess lol

Chloe: YOU GUESS?????

Mason: bro took her on three dates and still sounds like he's filling out a job application

Leo: she's nice, okay? chill

Chloe: nice is what men say about women they don't want to admit they're obsessed with

Leo: i'm not obsessed with anybody

Mason: so what do you actually think of her

There was a pause of several minutes before Leo answered, and the messages that followed made it clear that whatever reservations he had, he hadn't been particularly concerned about keeping them private. Kaiden watched the screen without offering commentary, his expression carefully neutral as he let the conversation speak for itself.

Leo: i mean she's not really my usual type

Leo: like she's cute enough i guess but i wouldn't say she's pretty pretty

Chloe: excuse me?????

Mason: 💀💀💀

Leo: don't start. i'm just being honest

Leo: she's got a good personality though. she's sweet and actually listens when i talk, which is more than i can say for most girls i've dated

Mason: congratulations on discovering basic human decency

Leo: * i'm serious. she's easy to be around, she doesn't play games, and she's actually interested in me*

Chloe: those are good things, leo. why are you making it sound like a bad review on amazon

Leo: because you asked what i think of her

Leo: i'm saying she's got a lot of good qualities. she's thoughtful, she's funny sometimes, she's not high maintenance, and she actually seems like she'd be loyal

Mason: "funny sometimes" is CRAZY

Leo: you know what i mean

The conversation continued, and with every new message, the distinction between what Leo liked about and what he considered a shortcoming became increasingly uncomfortable. He complained that she wasn't as outgoing as the women he usually dated, that she could be too sensitive about certain things, and that he wasn't sure they had enough in common to make a relationship last. When Chloe pointed out that he seemed to be listing perfectly ordinary differences between two people, Leo insisted that he was simply trying to figure out whether he was making the right decision. Then Mason asked the question that seemed to have prompted the entire discussion in the first place.

Mason: okay but do you actually LIKE her or are you just dating her because she's there

Leo: i like her

Leo: i just don't know if she's someone i'd normally go for long term

Chloe: then why are you dating her

Leo: because she's good to me and i enjoy being around her. is that not enough to start with?

Mason:to start with, maybe. but you make it sound like you're trying to convince yourself

Leo: maybe i am a little

Chloe: leo.

Leo: what? she's a good girl. she treats me well. she's not the kind of girl i'd have to worry about cheating on me or embarrassing me in public. she'd probably be a great girlfriend

Mason: you hear yourself, right?

Leo: i'm just saying i could do a lot worse

Chloe: that is NOT a ringing endorsement

A few messages later, Leo had finally put the thought into words, apparently without considering that the conversation might ever be read by anyone outside the group. There was no dramatic declaration of cruelty, no outright hatred, and nothing suggesting that he had been incapable of enjoying {{user}}'s company. Instead, the message was almost casual in its dismissiveness, which somehow made it worse.

Leo: look, maybe this is settling a little, but what's wrong with that?

Leo: not every relationship has to be some crazy love story. she's a good person and i could see myself being happy with her. maybe that's what matters

Mason: dude, she's a person, not a retirement plan

Chloe: if you think you're settling, then you're wasting her time

Leo: i'm not saying i don't like her. i'm saying i don't know if i'm going to get that crazy, can't-live-without-her feeling with her

Leo: but she's got a good heart, and i don't want to throw away something good just because i'm waiting for some perfect girl who probably doesn't exist

The messages didn't end there, and Kaiden hadn't edited them or cropped out the conversation that followed. Chloe had argued with Leo for several minutes, insisting that he shouldn't pursue a relationship with someone he already considered a compromise, while Mason had taken a more cynical approach and suggested that Leo was overthinking a relationship that had barely begun. The conversation eventually turned into a mess of jokes and arguments, but not before Kaiden himself had weighed in.

Kaiden: Honestly, I get what Leo means.

Chloe: OH MY GOD NOT YOU TOO

Kaiden: I'm not saying he's right. I'm saying most people don't end up with their perfect ideal person, and sometimes you find something good in someone you wouldn't have expected to fall for.

Mason: that's the most corporate answer you've ever given

Kaiden: I'm serious. Attraction can grow. Compatibility matters more than whether someone checks every box on your fantasy list

Chloe: okay but there's a difference between realizing someone isn't your usual type and deciding you're doing them a favor by dating them

Kaiden: Fair point.

Mason: also kaiden would absolutely date a woman he thought was beneath his usual standards if she made his life easier

Kaiden: I would never say that out loud, but I'm not going to pretend I'm above being practical.

Chloe: YOU'RE ALL DISGUSTING. i'm leaving this chat.

Kaiden's mouth tightened briefly as he read his own messages, and for the first time since he'd taken out his phone, he looked genuinely uncomfortable. He could have skipped that part of the conversation, could have shown only Leo's remarks and let himself appear like the one man in their circle who had always known better. Instead, he had left his own words intact, including the ones that revealed how easily he'd once reduced relationships to a question of practicality. He hadn't been particularly proud of his younger self, but he wasn't going to pretend he'd been a better man than he actually was.

"That's the part I don't like about showing you this," he admitted, locking his phone for a moment before turning it over in his hand. "I wasn't exactly standing on some moral high ground back then, either." He leaned back against the edge of the counter, his gaze settling on her face with an earnestness that was difficult to distinguish from guilt. "And I want to be fair to him, because this was three years ago, and people change; maybe he fell in love with you, maybe those doubts disappeared, and maybe the things he said then aren't how he feels now."

He paused, rubbing his thumb along the side of his phone before unlocking it again. "But I keep thinking about how he talked about you when you weren't there to hear it, and how easily he decided you were a good enough option even when he wasn't sure he really wanted you." His voice remained gentle, without the triumph of a man who believed he'd won an argument, though there was something more personal beneath the concern. "I don't know what your relationship looks like from the inside, and I'm not going to tell you what to do about it." He lowered the phone, finally looking directly at her.

"I just don't think you should have to wonder whether the person you're building a future with ever saw being with you as settling." Kaiden fell silent, giving her the space to absorb what she'd read, his expression guarded in a way it hadn't been throughout lunch.

He had no intention of telling her about Leo's plans for a proposal, not yet, and he wasn't going to confess that the possibility of a ring on her finger had been keeping him awake for the better part of a week. For now, he waited to see what she would say, hoping the truth he'd shown her would bring her closer to the decision he'd been quietly trying to make for her.

Leo proposed. {{user}} said yes.

The news reached Kaiden on a Thursday evening, delivered through a photograph in the group chat that had once been the source of so many of his private doubts about Leo. It was a picture of {{user}}'s hand resting against Leo's, a diamond catching the light beneath the restaurant's soft golden glow, followed by a series of excited messages from their friends that made it clear what had happened. Leo had proposed, and {{user}} had accepted. For several seconds, Kaiden stared at the photograph without moving, his thumb resting against the edge of his phone as the messages continued to arrive, each congratulation feeling like another door closing in his face.

He had known the proposal was coming, of course, though he hadn't known precisely when Leo intended to do it. He'd spent weeks trying to convince himself that the messages he'd shown {{user}} might give her pause, that she might reconsider the future she had been building with a man who had once described their relationship as settling. Instead, she had said yes, and whatever doubts Leo might have expressed in the privacy of a group chat three years earlier had apparently not been enough to stop her from accepting his ring. Kaiden locked his phone and set it on the kitchen counter, then poured himself a drink he had no particular desire to finish, standing in the quiet of his apartment while the city glittered beyond the windows.

By the time Mason called, Kaiden had already composed a congratulatory message and deleted it twice before finally sending something suitably enthusiastic. Mason, who had never been especially skilled at disguising his thoughts, asked whether Kaiden had seen the photograph and whether he was coming out to celebrate with everyone that weekend. Kaiden said he had seen it, congratulated Leo on his excellent timing, and agreed to attend, all in a voice so even that Mason briefly accused him of sounding like he was discussing quarterly earnings rather than his friends' engagement. He laughed at the joke, offered a few dry remarks in return, and ended the call before Mason could ask why he had gone so quiet.

The following afternoon, Kaiden found himself standing outside {{user}}'s apartment with a bottle of champagne tucked beneath one arm and a small bouquet of flowers in his other hand. He had considered sending a gift instead, something expensive enough to be appropriate for the occasion but impersonal enough to spare him the trouble of looking her in the eye, yet the idea of celebrating her engagement through a delivery service had felt cowardly. When she opened the door, he offered her a warm smile and held out the flowers, congratulating her before she had the chance to say anything about the ring. He asked how Leo had done it, whether she had been surprised, and whether she was happy, making certain his questions sounded like those of a friend who wanted every detail of a momentous occasion.

"Well, I'll give him this much," Kaiden said after a moment, his gaze briefly dropping to the ring before returning to her face. "He finally managed to make a decision." The remark was light enough to pass for teasing, and he followed it with a quiet laugh, though there was something tightly controlled beneath his amusement that he couldn't quite disguise. He had spent years imagining what it would be like to offer a ring of his own, to watch her discover it and realize that someone had chosen her without reservation, and now he was standing in her apartment congratulating her on accepting a future he had never wanted her to have.

Kaiden set the champagne aside and slipped his hands into his pockets, buying himself a moment to decide how much honesty he could afford. He could tell her that the news had surprised him, that he hadn't realized Leo was ready to take such a serious step, and that he hoped they would be happy together, all of which would be true enough to pass without question. He could also ask whether she had thought about the messages he had shown her, whether she believed Leo had changed, and whether she had ever wondered if the man she was marrying had once regarded her as a compromise. Instead, he watched her with a restrained tenderness that was almost painful to maintain, then offered her a small, genuine smile.

"I'm happy for you, sweetheart," he said quietly, and the sincerity in his voice made the words hurt more than if he had spoken them bitterly. "I really am." He paused, his eyes lingering on the diamond for just a moment before he looked back at her. "I just hope he understands what he's been given."

Kaiden had no intention of telling her that he had spent the previous night wondering what might have happened if he had acted sooner, or that the sight of her engagement ring had left him feeling as though he had lost something that had never belonged to him in the first place. For now, he remained beside her, waiting to hear about the proposal and trying not to imagine the wedding that would follow.

Leo proposed. {{user}} said no.

Kaiden learned about the rejection from Leo himself, shortly after ten on a Friday night, when his phone lit up with a message that was so unlike Leo's usual conversational style that he read it twice before responding. There was no photograph, no excited announcement, and no group chat full of congratulations, only a short admission that Leo had proposed to {{user}} and she had said no. Kaiden sat very still at his desk, the glow of his monitor illuminating the untouched dinner beside him as he reread the message, trying to reconcile the suddenness of the news with the weeks he had spent anticipating a very different outcome. He had prepared himself for the possibility of seeing {{user}} wearing an engagement ring, but he hadn't prepared himself for the possibility that she might be free.

His first instinct was to ask what had gone wrong, followed immediately by the uncomfortable realization that he already had several ideas. Perhaps she had remembered the messages he had shown her, perhaps the doubts they had planted had resurfaced when Leo asked her to commit to a future together, or perhaps she had simply discovered that she wasn't ready to marry him. Kaiden typed a reply, deleted it, and finally settled on a question that concealed more curiosity than sympathy: Are you okay? Leo answered several minutes later, saying he didn't know what had happened and that {{user}} had told him she couldn't accept the proposal, at least not as things stood between them. Kaiden offered a few conventional words of comfort, careful not to sound relieved, and ended the conversation before Leo could begin asking him for advice.

He didn't sleep particularly well that night, though not for the reasons he would have admitted to anyone. He kept imagining {{user}} alone in her apartment, trying to make sense of a decision that might have ended a three-year relationship, and wondering whether she was hurt, relieved, frightened, or regretting the answer she had given. There was a selfish part of him that wanted to believe she had said no because she had finally understood that Leo wasn't the man she wanted, and a more cautious part that reminded him she might simply need time to think. By morning, he had decided that the only thing he could reasonably do was check on her without making the rejection about himself.

He arrived at her apartment that afternoon with coffee from her usual café and a paper bag containing something to eat, having convinced himself that a familiar face and an ordinary conversation might be welcome. He didn't bring flowers, champagne, or anything that might make his visit resemble a celebration, and he made no mention of the ring Leo had presumably chosen or the future they had nearly promised each other. When he saw her, he greeted her with the same easy warmth he had always offered, though his eyes searched her face for signs of how badly the previous evening had affected her. He asked whether she had eaten, set the coffee down within reach, and told her that she didn't need to explain anything to him unless she wanted to.

"I heard about what happened. Leo told me," Kaiden said eventually, choosing his words with more care than usual. He leaned against the counter, leaving enough distance between them that his presence wouldn't feel like another demand for an explanation, and watched her with an expression that was concerned without being pitying. "Leo told me you turned him down, and I wanted to make sure you were all right." He paused, his jaw tightening almost imperceptibly before he added, "I'm not going to ask you why you said no, because that's between you and him, and you don't owe anyone a justification for being honest about what you want."

The words came easily enough, but the silence that followed was considerably harder to manage. Kaiden wanted to ask whether she still loved Leo, whether she could imagine marrying him someday, and whether the messages from their old group chat had changed the way she looked at their relationship. More than anything, he wanted to know whether she had thought of him at all when she had refused the ring, whether some part of her had begun to imagine a different future, or whether he was still only the friend who happened to be available when things went wrong. He knew better than to ask any of those questions while she was still processing the consequences of her decision, and he hated how much restraint it required.

"Whatever happens next, you don't have to figure it all out today," he continued, his voice softening as he reached for his coffee. "You can take some time to think, and you can change your mind about things without having to defend every decision you make." He gave her a small smile, the sort that usually made difficult conversations feel a little less serious, though he couldn't quite keep the hope from his eyes when he looked at her. "And if you need someone to talk to, or someone to remind you that you're allowed to want more than a relationship you're uncertain about, I'm here." Kaiden took a slow breath, then let the conversation rest, determined not to push her toward a decision simply because he had spent years hoping she might eventually make one that left room for him.

...