I Helped My Awkward Friend with a Girl, Only to Find Her Number in My Pocket Afterward – Story of the Day

When Jake agreed to help his shy best friend with a first date, he never expected to become part of the story. But a secret note slipped into his jacket by the girl changes everything—leaving him between loyalty and the chance at something more.

That evening, the restaurant buzzed with the usual clinking of glasses and low chatter.

I leaned against the bar, exchanging small talk with Irene as she methodically polished a row of wine glasses.

The warm light reflected off the glassware, casting tiny rainbows onto the counter.

“You’re awfully jittery tonight,” Irene remarked, pausing mid-polish. Her sharp eyes caught me glancing toward the door again.

“What’s got you all wound up? Waiting for someone?”

I hesitated before answering. “Kind of. My friend Neil’s coming by. But, uh… it’s not me he’s here to see.”

Her brows lifted, a curious smirk tugging at her lips. “Oh? Sounds interesting. Spill it.”

I chuckled, leaning in closer like I was about to share a secret. “He’s got a date tonight. With a coworker he’s been mooning over for years.”

“Years?” Irene placed the glass down with a soft clink. “And he’s just now asking her out? What’s his deal?”

“He’s shy. Really shy,” I admitted. “But he’s a great guy. Sweet, smart, the whole package. He just… needs a little nudge.”

“Let me guess,” Irene said dryly. “You’re the nudge.”

Before I could reply, her eyes flicked to the entrance. “Looks like your project just walked in.”

I turned and winced. Neil stood awkwardly by the door, dressed in a suit that seemed two sizes too big, his glasses perched precariously on his nose.

His hair was slicked back like he’d borrowed too much gel from the 1980s, and in his hands was a bouquet of roses—bright, red, and far too formal for the setting.

“Yikes,” I muttered under my breath, rising from my seat. “We’re in critical territory.”

“Good luck,” Irene called after me, stifling a laugh.

“Neil!” I greeted him while clapping on his back. “You clean up… sharp.”

“Do I?” he asked, looking doubtful.

“I wasn’t sure about the suit, but I thought it’d make a good impression.”

“It makes an impression, all right,” I said. “Let’s fine-tune a little.”

I led him to the best table in the house, right by the window with a view of the city lights.

Usually reserved for VIPs, this spot was perfect for setting the right tone—Neil needed all the help he could get. Once seated, I leaned over to tousle his hair.

“Jake! What are you doing?” he protested, swatting my hand away.

“Trust me, you’ll thank me later. And these…” I snatched his glasses.

“Off for now. First impressions matter.”

“I can’t see without them!” he whispered, panicked.

“Consider it a temporary sacrifice for the cause,” I said, pocketing them.

“And the roses—give those to me. I’ll deliver them when she gets here. Adds a little flair.”

Neil handed them over reluctantly. “What if… what if she doesn’t like me?” he asked, his voice barely above a whisper.

“She’s already coming to meet you,” I reminded him, placing a reassuring hand on his shoulder.

“You’ve got this. Just be yourself. But, you know, confident. Cool.”

Neil gave a shaky nod as I returned to the bar, watching him fidget nervously. Irene joined me, smirking as she surveyed the scene.

“Think he’ll pull it off?” she asked.

“He’s got a chance,” I said, though I wasn’t entirely convinced.

The moment she stepped into the restaurant, she drew every eye in the room, including mine.

She had an easy grace about her, wearing a simple yet elegant dress that made her look effortlessly stunning.

I didn’t need confirmation—Neil’s frozen expression said it all. He looked like a deer caught in headlights, his jaw slightly slack.

“Your friend’s got good taste,” Irene whispered from behind me, a playful grin tugging at her lips.

“She’s stunning,” I muttered, almost to myself.

Irene gave me a teasing nudge. “Careful, cowboy. That’s your buddy’s future wife. Or at least she will be if he doesn’t blow it.”

Neil, however, was on track to do exactly that. He was clearly overwhelmed, hiding his face behind the menu like a shield.

Across the table, she scrolled through her phone, her expression polite but distant. It was painfully obvious that things weren’t going well.

I couldn’t watch it fall apart. Picking up the bouquet of roses, I strode to their table, determined to salvage the night.

“Good evening. I’ll be your waiter tonight, and these are for you,” I said, handing the flowers to her with a warm smile.

Her face lit up, her smile genuine. “Oh, thank you! Who are they from?”

I nodded toward Neil, who was staring so intently at the tablecloth that I thought he might set it on fire.

“The gentleman sitting across from you.”

Her smile wavered slightly, but she glanced at Neil and politely nodded. “That’s very sweet. Thank you.”

Taking their orders, I cracked a small joke to lighten the mood. She laughed softly, but Neil barely mumbled his order.

Returning to the bar, I sighed heavily. This was going to be a long evening.

An hour later, the scene was winding down. She stood, slipping her purse over her shoulder and glancing at Neil with a polite but distant smile.

Neil quickly jumped up, fumbling to offer something—a handshake, a hug, or just his words. “Would you like me to walk you to your car?”

She shook her head lightly, her tone kind but firm. “No, thank you. I’ll be fine. It was... nice meeting you, Neil. Take care.”

“Take care,” he echoed, standing awkwardly by the table as she walked away. I couldn’t help but notice she didn’t look back.

Neil approached the bar, his face surprisingly bright. “Well?” I asked cautiously, keeping my tone neutral.

“It went great!” he exclaimed, his grin wide. “I was so nervous, but I think it went really well.”

I blinked, unsure of how to respond. “You’re sure? It seemed kind of... short.”

“Oh, she mentioned she had other plans she forgot about. No big deal,” he said with a wave of his hand.

“I’m sure we’ll meet again. She seemed interested.”

I wanted to say something, to manage his expectations, but the light in his eyes stopped me. I forced a smile.

“That’s great, buddy. Really great.”

With a confident nod, Neil left, his step light as he walked out the door.

I returned to cleaning up, trying to focus on my tasks, but something about the night still felt unresolved.

Later, while changing out of my uniform in the back, I reached into my jacket pocket and felt something crinkled.

I pulled it out—a napkin with a note scribbled on it. My heart did a strange little flip as I read the words:

“Would love to get to know you better, sweet waiter. —Liz”

Liz.

My mind raced. She must have slipped it to me during the dinner. The idea made my stomach tighten with a mix of emotions.

Part of me felt a thrill—she was gorgeous, and I’d felt a connection too. But then came the guilt, heavy and immediate. Neil liked her.

Neil thought their evening went well. And here I was, holding a note from the woman he’d been dreaming about for years.

I folded the napkin carefully, slipping it into my bag.

The possibilities felt both exciting and impossible. What was I supposed to do now?

The next morning, I stood outside Neil’s office building, the napkin still tucked in my pocket, feeling heavier than it should.

My mind was a swirling mess of guilt and uncertainty.

I kept replaying the previous night’s events, wondering if I should’ve ignored the note or thrown it away. But here I was, waiting, unable to let it go.

The glass doors opened, and Liz stepped out, looking radiant in the sunlight.

She spotted me immediately and smiled, her eyes lighting up like I’d made her day just by being there. It was both thrilling and terrifying.

“Jake!” she called, walking toward me. “You found the napkin! I was worried you might not see it.”

Her enthusiasm caught me off guard. “I did,” I said hesitantly. “But—”

“I couldn’t stop thinking about you after last night,” she interrupted, her voice soft but insistent.

“I don’t know what it was, but there was something… different. I felt a connection.”

Before I could respond, a familiar voice cut through the moment like a blade. “Jake? Liz? What’s going on?”

I felt like I’d been caught doing something wrong, even though I hadn’t done anything. Not yet, anyway.

“Neil,” Liz began, her tone calm but firm. “I was hoping to talk to you. I don’t think there’s going to be a second date.”

“What?” Neil’s face fell. “But last night… I thought it went well. I thought we had something.”

Liz hesitated. “You’re a great guy, Neil, but I didn’t feel a spark.”

Neil’s eyes narrowed, shifting to me. “Is it him? You like him?”

“Neil, this isn’t about Jake,” Liz said quickly.

“Don’t lie to me!” Neil snapped. “He’s just a waiter! He’s nothing! And you’re going to pick him over me?”

“Neil, stop,” Liz said, her voice sharp now. “This isn’t fair to anyone.”

“I’m not your enemy, Neil,” I said carefully, stepping forward. “I didn’t plan this.”

“You’re not my friend either,” Neil spat, his voice trembling with anger.

“Stay away from me.” Without another word, he turned and stormed off, leaving a tense silence in his wake.

Liz sighed, running a hand through her hair. “I didn’t want it to happen like this,” she said quietly, her voice tinged with regret.

“Neither did I,” I admitted, the weight of the situation pressing down on me.

We stood there for a moment, the awkwardness hanging in the air. Then Liz looked up at me, a small, hopeful smile creeping onto her face.

“But… I’d still like to take you out for coffee. If you’re up for it.”

I hesitated, the image of Neil’s devastated face flashing in my mind. But then I looked at Liz, her expression so genuine and open, and I couldn’t say no.

“I think I know a good spot nearby,” I said, smiling back.

“Perfect,” she said, looping her arm through mine like it was the most natural thing in the world. “Let’s go.”

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