That Time We Hosted the Proposal That Went (Very) Wrong

Jan 22, 2022 | Improve Ratings, Maximize Earnings

That Time We Hosted the Proposal That Went (Very) Wrong

You know those moments in life that make you cringe? The moments when, no matter how much time passes, you remember where you were when it happened and exactly how it made you feel. I have such a moment I’m going to share with you today.

It was early spring 2019. My husband and I received a request-to-book inquiry on Airbnb, but this one looked different than most. This fella – let’s just call him Earl – was in Nashville by way of his construction gig and wanted to bring his girlfriend into town to propose to her, aw. But Earl had zero reviews and asked if we could hold the dates he’d requested until he got paid that Friday. Hard pass, right? Except Earl further explained that he had not only just covered his girlfriend’s rent but also the cost of his mother’s funeral…you know, just your average guest inquiry.

Here’s the thing. While holding dates at the request of a random guest isn’t something any seasoned host would or should do for over 24 hours, we felt for the guy. I’d been in his shoes before (well…maybe mine were more akin to a soft pair of fuzzy slippers) with living paycheck to paycheck, and this was a really special occasion for him. Although these types of situations don’t usually end well for hosts, we relented and agreed to hold the dates until Friday.

Here comes Friday! Oh look, another message. This time our prospective guest is frantically trying to get to the bank by 5pm to deposit his check but he’s “on the bus” and “traffic is bad” and he’s “so stressed out he’s not going to make it in time” and can he pay us in the morning…

By this point, if you didn’t already think we were crazy, you certainly would if we were to continue holding the dates for him now.  Avoids eye contact.

But guess what, Negative Nancy – ‘ole Earl did book with us later that very evening! Well, after a few remarks about the total price being higher than expected. What an adventure this was shaping up to be.

On the one hand, we were glad we’d solidified the booking after all the rigmarole and were hoping we’d done the “right thing.” On the other hand…well. Let’s just say, with hosting, you may always be one guest away from a nervous breakdown.

Nevertheless, Earl was excited. No – “excited” is an understatement. With notification pings like “I love this beautiful woman so much” and “she is my world” harassing me throughout my workday, I’d say sweet Earl was closer to a soft state of solid euphoria. I digress.

The big weekend finally arrives and with bated breath, we welcome Earl and the love of his life into our beloved home…casually monitoring every second of their arrival through our security camera. Keeping a watchful eye out for our neighbors, of course. Responsible hosts and all.

Ok fine, we were nervous. Based on the colorful communication we’d had with Earl, we didn’t know what kind of behavior to expect from them as guests.

But much to our surprise, all seemed okay… In fact, we didn’t hear another peep from Earl until the second night of his 3-night stay. He sent us a brief message around 10pm explaining how he had to be back at work very early the next morning and wanted to go ahead and check out.

And just like that, I knew something went terribly wrong.

This sounded less like a man who had just gotten engaged and more like a lyric from Champagne Problems. But like any concerned (nosy) host, I had to ask what happened. How to ask was the question. The unfortunate exchange went a little something [exactly] like this:

“May we ask if the proposal went as planned?…”

“No, I found out she was sleeping with another man.”

Some things ain’t covered in an Airbnb Masterclass.

What in the world could I possibly say to this. We just felt awful for the guy. He had recently buried his mom, was financially strained, and had just put a chunk of his hard-earned paycheck (and pride) towards securing a beautiful short-term rental for this “special” occasion. Not to mention he had paid rent for this girl! Poor Earl just couldn’t catch a break.

After taking a moment to recover from the unyielding cringe I was experiencing, I considered the best course of action. My husband (who graciously handed this one off to me…) and I had been pretty intimately involved in these proposal arrangements and felt a bit like his virtual support system by this point. I wanted to offer some consolation but knew there was nothing I could say that would make his situation any less painful. I gently expressed my condolences and thanked him for his communication.

While we were truly sad for Earl, we also couldn’t help but wonder what state we would find our home in after a potentially heated exchange between the former couple. Holes in the wall, broken dishes, liquor bottles strewn about…you know, the usual places hosts’ imaginations run full speed to.

This is where things took a turn we were never expecting.

Earl informed us that – in addition to the few checkout requests we had in our house manual –

he had washed the linens, remade the bed, and washed and rehung the towels. All this after finding out the woman he’d hoped to spend the rest of his life with was cheating on him.

The next day, I drove over to the rental. As I walked inside, my heart dropped. It looked as if no one had even been there. Everything was spotless – every towel folded perfectly in thirds, every throw pillow placed in its proper position, every bed made up just so. In that moment, all I could feel was heartbreaking conviction.

From our very first contact with Earl, my husband and I had underlying prejudices regarding what type of guest he would be. In short, we thought he’d be a hot mess. You know, the oblivious kind that thinks keeping a window open and a can of Glade spray handy while smoking is a thoughtful solution to dodging a no-smoking rule. We couldn’t have been more wrong.

Hosting teaches valuable lessons to us all. This day and age, it’s far too easy to make quick judgments of people from behind a screen. For my husband and me, we’ve been taught many lessons in humility over the years – this one being no exception.

We’ll never forget Earl. In all his expressive glory, he certainly left his mark in our lives. When I think of him, I think of him with fondness. And we’re better hosts because of him.

We’ve learned a lot from our past misconceptions and hosting blunders, and we’re here to help you glean what wisdom you can from our mistakes so you don’t have to learn some of these things the hard way. If you need any kind of help or guidance with your hosting strategies, we would love to support you however we can. You can schedule a consultation with us here.

To all the Earls in the world, thank you.

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