I Went Caroling On A First Date & It Was Even More Ridiculous Than I Expected

I'm one of those people who likes to say she'll do anything once, especially when it comes to dating. I've asked hot guys to bring me pizza during snow storms, flown to San Francisco to hang out with strangers, and now, I can also say I've gone caroling on a first date.

The idea of caroling in London sounds so Love Actually, doesn't it? I thought so, too. My vision included wearing turtleneck sweaters, strolling through the pastel-colored streets of Notting Hill and singing "Good King Wenceslas" to adoring children, then cozying up to my cute, British caroling partner in a pub while Mariah Carey's "All I Want For Christmas Is You" plays in the background.

But — like most of things in life — my expectations didn't exactly align with reality.

Honestly, I'm not sure what the most ridiculous part of this story is. That it all began with me texting a near-stranger from a dating app and saying, in all caps, "YES HELLO WILL YOU GO CAROLING WITH ME?" That this stranger actually said yes? That neither of us really knew how or where to go caroling, and basically just started wandering the streets singing? Oh, or was it the fact that I did all of this with a bad case of laryngitis and consequently sounded more like a squawking newborn chicken than an actual caroler? I'll let you decide. Here's how it all played out.

I begged strangers to carol with me.

Over the last few weeks, I'd asked a couple of gentlemen to fulfill my Love Actually fantasy and go caroling with me, but no one had come through. One fellow agreed, then completely ghosted me the weekend of our date. The second guy rescheduled like a million times due to "work commitments."

Then, a guy named Daniel messaged me on a dating app and pretty quickly told me a story about how he once rolled into a store drunk, claimed he was the manager, and demanded free merchandise. He seemed like a good fit for my ridiculous request.

A few days later, I sent him that all-caps text asking if he'd like to carol with me. He responded with, "Would we carol with randos? Or would we carol outside a station like for money? I can just print us off a bunch of lyrics and let alcohol do the rest."

Excellent. The plan was a-go.

We turned to the pros (well, we tried to).

A few days later, we met up at a pub in central London and Daniel explained that he was pretty sure there was an outdoor caroling service a few blocks away. Why not grab a beer and then join the professionals?

We chatted about our favorite holidays movies and where to grab the best pizza in London. There wasn't an instant love connection, per se, but we got along like old friends, and I was stoked to listen to some Christmas music.

But an hour or so later when we decided to scope out these carolers, no one was around. It was a totally silent night (see what I did there?).

What now?

The show went on!

Oh yeah, we just started singing in the street. I'd like to say that it played out like Zooey Deschanel singing "Santa Claus Is Coming To Town" in Elf, with the whole city joining in, but it most certainly did not.

Daniel hadn't really printed off those lyrics, so we were working from memory here. I basically just squawked the lyrics to "Jingle Bell Rock." Bystanders looked deeply confused, and inexplicably, no one offered us money for our beautiful performance.

We realized we were not cut out for this.

After wandering around and singing for about 30 minutes (which may or may not have involved a few strangers yelling, "Shut the h*ll up!"), we decided to call it quits and made our way back to the pub.

Was this one of the weirder dates I've been on? Absolutely (and this is coming from a woman who once tried to scale the fence of Sacré-Cœur on a first date). But I also laughed until my cheeks hurt and had such a blast. I think it's safe to say that Daniel and I lacked physical chemistry from the get-go, but that didn't put a damper on the fun of caroling together. Why not give caroling a try on your next date? After all, 'tis the season.

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