Best Man: A Wedding Weekend Romance

The wedding invitation arrived in a pale blue envelope with gold lettering, and I knew before I opened it that the next three days were going to be hell.

Not because of the wedding itself. My college roommate Derek deserved happiness, and his fiancée Emma was great. I was genuinely thrilled for them. No, the problem was the best man situation.

Derek had two best men. Me—his college roommate and closest friend for fifteen years—and his older brother Will. The same Will I'd hooked up with four years ago at Derek's thirtieth birthday party after too many shots of tequila. The same Will who'd ghosted me the next morning and never acknowledged it had happened. The same Will I'd been actively avoiding ever since.

Three days. One destination wedding. Two best men who had to share a room because the resort was fully booked.

What could possibly go wrong?

🏝️ Sunset Cove Resort The resort was beautiful. I'll give them that. Beachfront property on an island that looked like it had been designed by someone whose only job was making Instagram jealous. Palm trees, white sand, water so blue it hurt to look at.

I arrived Friday afternoon, checked in, and immediately ran into the one person I'd been hoping to avoid until the last possible moment.

"Sam."

Will was standing in the lobby, rolling a suitcase behind him, looking exactly as unfairly attractive as I remembered. Tall. Broad shoulders. Jaw that could cut glass. Eyes the same shade as his brother's but with something sharper behind them.

"Will."

We stared at each other. Four years of not talking, and neither of us knew how to start.

"I guess we're roommates."

"Guess so."

"That's not going to be weird at all."

"Not at all."

More staring. Then, inexplicably, we both started laughing. The tension didn't break exactly, but it cracked just enough to make the next three days feel slightly less impossible.

"Come on," he said. "Let's go see how small this room is."

The room was not small. It was actually gorgeous—king-sized bed, ocean view, balcony with a hot tub. The problem was the bed situation. One bed. One very large bed, but still. One.

"I'll sleep on the floor."

"Don't be stupid. We're adults. We can share a bed."

"Can we?"

He didn't answer. Just started unpacking like the question didn't matter.

This was going to be a long weekend.

The rehearsal dinner was that night. Open bar, which I took full advantage of. Three whiskeys in, my anxiety had dulled enough that I could almost pretend Will and I were just two people who happened to know the same groom.

Almost.

"You've been avoiding me all night."

He'd cornered me on the terrace. Everyone else was inside, dancing to the live band the venue had provided. Out here it was just us and the ocean and the thing we'd never talked about.

"I haven't been avoiding you. I've been mingling."

"You literally turned around and walked the other way when I tried to talk to you at the appetizer table."

"Those crab cakes were in high demand. I had to act fast."

"Sam."

"What do you want me to say, Will? That it's weird being here with you? That I spent four years trying to forget what happened and now we're sharing a bed at your brother's wedding? It's weird. It's really weird."

"I know it's weird. I'm trying to make it less weird."

"By cornering me on a terrace?"

"By talking about it. Finally. Like we should have done the morning after instead of me panicking and leaving."

I looked at him. Really looked. He seemed uncomfortable in a way I wasn't used to seeing. Will was always the confident one, the one who had his life together, the one who made decisions and stuck to them. Seeing him uncertain was disorienting.

"Why did you leave?"

"Because I was scared. Because I'd never done anything like that before. Because I woke up next to you and realized I'd felt more in one night than I had in my entire three-year relationship with my girlfriend, and I had no idea what to do with that."

"So you ghosted me."

"I panicked. I'm not proud of it."

"You could have called. Texted. Anything."

"I know. And I've regretted it every day since. I just didn't know how to fix it."

"Four years is a long time to not know how to fix something."

"I know that too."

We stood there, the sounds of the party drifting through the windows behind us. The ocean crashed against the shore below. Someone inside cheered about something.

"I'm not going to pretend it didn't hurt. Because it did. A lot."

"I know. And I'm sorry. Really, truly sorry."

"Okay."

"Okay?"

"Okay, I hear your apology. I'm not saying everything's fine. But we have to get through this weekend without making it awkward for Derek and Emma. So... okay. Let's just try to be normal."

"Normal. Right."

He looked like he wanted to say more. But I was already walking back inside, my heart pounding in a way I didn't want to examine.

🌙 Night One Sharing a bed with Will was exactly as awkward as I'd expected.

We stayed on opposite sides, a careful strip of no-man's-land between us. I faced the window. He faced the wall. Neither of us slept much.

At some point in the middle of the night, I heard him say my name. Quiet enough that I could pretend to be asleep if I wanted.

I didn't want to.

"Yeah?"

"Can I tell you something?"

"Sure."

"I never dated anyone after that night. The girlfriend I mentioned—I broke up with her the week after. And I haven't been with anyone since."

I turned over. He was already facing me, a shadow in the darkness.

"Why not?"

"Because every time I thought about trying, I thought about you. About how it felt to be with you. And nothing else seemed worth the effort."

"Will..."

"I know it's too late. I know I messed it up. But I wanted you to know. You weren't just some random hookup to me. You were the moment everything clicked. I've just been too scared to do anything about it."

I didn't know what to say. Four years of hurt, four years of wondering what I'd done wrong, four years of trying to move on—and it turned out he'd been just as messed up as me.

"Go to sleep, Will."

"Okay."

He turned back to the wall. I turned back to the window.

Neither of us slept.

📅 Wedding Day The ceremony was at sunset. Gold and pink light spilling across the beach, flowers everywhere, Emma walking down an aisle of white sand toward a groom who was crying before she even reached him.

Will and I stood on either side of Derek, matching suits, matching boutonnieres, definitely not looking at each other.

Except I kept looking at him. Couldn't help it. And every time I did, he was looking back.

The vows were beautiful. Something about finding your person, about being brave enough to choose love even when it's terrifying, about waking up every day and deciding to be there. Emma's voice shook. Derek's voice shook more. Half the audience was crying.

I thought about Will. About the night we'd shared. About his confession in the darkness of our hotel room. About what it might mean to be brave enough to choose love.

When they kissed, everyone cheered. Will and I clapped along with everyone else. Our eyes met across the flower arch.

Something had shifted. I could feel it. The question was what I was going to do about it.

The reception was chaos in the best way. Dinner, toasts, dancing that started awkward and got progressively drunker as the night went on. Derek and Emma couldn't stop smiling. Will and I couldn't stop circling each other.

It was during the slow songs that he finally approached me.

"Dance with me."

"People will talk."

"Let them."

He held out his hand. I took it.

We danced. Slowly, carefully, keeping a respectable distance because this was still my best friend's wedding and we were still supposed to be acting normal. But his hand was on my waist, and my hand was on his shoulder, and the song was something slow and romantic that made everything feel more significant than it probably was.

"I meant what I said last night."

"I know."

"And?"

"And I don't know. I spent four years trying to get over you. Telling myself it was just one night, just a mistake, just something to forget."

"Was it? Something to forget?"

"No. Obviously not. I'm still here, aren't I? Still dancing with you at your brother's wedding like an idiot."

"I like that you're an idiot. I like a lot of things about you."

"Will."

"Give me another chance. Please. I know I don't deserve it. I know I should have done this years ago. But I'm asking now. Give me a chance to do this right."

The song ended. Another one started. We kept dancing.

"If I say yes—and I'm not saying yes yet—you have to promise me something."

"Anything."

"No more running. No more ghosting. If you get scared, you tell me. If you're confused, you tell me. We actually talk about things like adults."

"I promise."

"And you tell Derek. Tomorrow. Before we leave. I'm not being your secret."

"I'll tell him tonight if you want."

"Tomorrow is fine. Let him enjoy his wedding night."

Will pulled me closer. Close enough that I could feel his heart beating through his suit jacket.

"Is that a yes?"

"It's a maybe. A strong maybe."

"I can work with a maybe."

🌙 Night Two We didn't stay on opposite sides of the bed that night.

We talked first. For hours. About everything we'd been holding back. His struggle with his sexuality—he'd never told anyone, not even Derek. My hurt after he left—deeper than I'd admitted to myself. The years between—the almost-relationships, the self-doubt, the way we'd both been stuck.

And then we weren't talking anymore.

The kiss was different this time. Not fueled by alcohol. Not rushed or reckless. Slow. Intentional. The kiss of two people who knew what they were getting into and were choosing it anyway.

"Are you sure?" he asked, pulling back just enough to see my face.

"I've had four years to be unsure. Tonight I'm sure."

We undressed each other slowly. Took our time. He touched me like he was trying to memorize every inch. I touched him like I was making up for lost time.

When we finally came together, it was with the kind of intensity that only builds over years of wanting. He moved above me, inside me, around me—everywhere at once. I held on and let myself fall.

"I love you," he said, right at the edge. "I know it's crazy. I know we barely know each other outside of this. But I love you."

"I love you too. Have for years. Hate you a little for it."

"I can live with that."

We finished together. Stayed wrapped around each other afterward, catching our breath, listening to the waves outside. The room was silver with moonlight. His face was soft in a way I'd never seen before.

"Stay."

"I'm right here."

"Not just tonight. Stay. In my life. For real this time."

"Okay."

"Yeah?"

"Yeah. No more maybes."

He kissed me again. And again. And again.

We didn't sleep much that night either. But this time it was for very different reasons.

Will told Derek at the farewell brunch the next morning. Pulled him aside while Emma and I made small talk about honeymoon plans.

I watched from across the room as Derek's face went through about seventeen different expressions in thirty seconds. Shock. Confusion. More confusion. And then, finally, something that looked like relief.

He hugged his brother. Looked over at me. Gave me a thumbs up and a grin.

Emma caught my eye.

"Called it," she mouthed.

Apparently everyone had been waiting for this except us.

⏳ One Year Later We moved in together after six months. A small apartment that was technically his but became ours. His stuff mixed with my stuff until neither of us could remember what belonged to whom.

Derek made jokes about being related to me now. Emma started calling me her brother-in-law even though no one had proposed to anyone yet. Will's parents took a little longer to come around, but they got there eventually.

And every year, on the anniversary of Derek and Emma's wedding, we went back to that resort. Same room. Same bed. Same ocean view.

We'd walk along the beach where they got married. We'd dance on the terrace where we'd had our first real conversation in four years. We'd remember how close we'd come to never trying at all.

"Worth it?" he'd ask every time.

"Worth everything."

Sometimes the best stories start with the worst situations. Sometimes the person you've been avoiding is the person you should have been running toward. Sometimes it takes four years and a destination wedding to figure out what you had all along.

Will was my second chance. My best man. My person.

And I was never letting him go again.