‘You don’t think a scavenger hunt is romantic?’ asked my client Michael*.
He’d just suggested sending his girlfriend on a wild goose chase across Manhattan, retrieving clues from his exes in the order he’d dated them – I was horrified.
But as a proposal planner, my role was to focus on logistics rather than acting as a gatekeeper of perceived ‘romance’.
Luckily, most men (and a few women) who came to my company for help weren’t married to their own ideas and I was usually able to provide them with a better alternative.
So, I tactfully replied: ‘Navigating New York during rush hour isn’t exactly an ideal time to solve riddles around town.’ And then I came up with a new suggestion…
Instead of sending her across the whole city, we’d station musicians at various landmarks in Central Park to serenade her with specific songs from pivotal moments in their relationship. The final stop would be the iconic Bow Bridge, which is where he would drop to one knee.
He gave it the green-light and I set about getting everything organised just like I had a hundred times before.
Yet this was never a job I dreamed of doing. In fact I sort of fell into it by chance.
I was 20 years old and job-hunting when I found an advert on Craigslist listing a content managerial role for a blog and social media company.
When I discovered the unique nature of the business – that the company offered proposal planning and photography services in every major city in the United States (plus Paris and London) – I was pleasantly surprised.
I’d always imagined proposals as super intimate moments that lived as stories passed down to the next generation. And as a hopeless romantic, I loved the idea that I’d have the opportunity to be a part of so many happy memories.
The company had a national network of freelance photographers, and it was my job to manage all the content, including interviewing people after their proposals on how they met and eventually fell in love with their partners.
After a promotion, the owner and I planned each proposal from our base in New York. But each one was carried out in a manner more akin to a Secret Service operation than a romantic gesture.
We coordinated banners flown across the sky, flash mobs and boat rides all with the help of meticulously outlined plans, maps and diagrams.
There were even stick figures drawn on the maps to specify where everyone should be positioned for the picture-perfect kneeling shot.
Generally speaking, most proposals I arranged tended to occur at public parks, in front of the ocean, or on rooftops, as these types of locations offered the most striking scenery. However, my personal favourite location to work with was the La Jolla Cliffs in San Diego.
It involved discreetly positioning the photographer like a spy on a cliff above while the client escorted his partner below, facing her back towards the ocean, enabling us to capture her reaction perfectly. The shots were mesmerising.
By the time I’d been with the company for a few years though, there wasn’t an idea I didn’t already have an outline template for somewhere in my email.
I was forever planning proposals in some of the most iconic locations in each city – think South Beach in Miami, Boston Commons in Boston, and Malibu in Los Angeles. However, Central Park in New York was undoubtedly the most popular.
Granted, Michael’s proposal was a bit more complicated than that. I coordinated for a photographer to shadow his girlfriend like a paparazzo as she made her way from musician to musician, clandestinely capturing the moment until he proposed.
On Bow Bridge a guitarist sang Bruno Mars’ Marry You as Michael stood poised at the centre with a diamond ring. She cried tears of joy and said yes. And immediately after, the pair had a portrait session – almost a mini engagement shoot – so they could forever remember this special moment.
In total, Michael spent $1,875 on his proposal but this was not uncommon. Most clients tended to spend anywhere from $1,000 to $3,000, which wasn’t a bad deal considering photography and planning were included – but I did see a handful of people spend hundreds of thousands on ridiculously costly hotels and chartering private jets too.
So, contrary to my original belief, it wasn’t a job for hopeless romantics. I quickly learned my job wasn’t to make ‘magic happen’ but to ensure the logistics aligned with reality – and their budget.
We faced challenges on more than a few occasions – though, thankfully I never encountered a client being turned down. Issues mainly stemmed from clients being dissatisfied with their appearance in photos.
It was intriguing to observe how the quality of the photos directly correlated with a client’s satisfaction level.
Personally, I soon felt I was aiding and abetting the commercialisation of romance. Some clients acted like their partner’s answer was predetermined and so were more concerned with having an Instagram-ready backdrop over anything else.
That’s hardly surprising given the importance of photography in the era of social media – and I truly don’t think the proposal industry would be so profitable if it wasn’t for the money shot – but it saddened me to see how many people seemed to care more about posting their proposal on Instagram than enjoying the actual moment.
I also found it increasingly hard to ignore the palpable irony in my life – I was young and inexperienced with commitment, yet helping people commit was my job.
Honestly though, given the world I worked in, I had such a warped sense of romance. I exclusively dated wealthy men throughout my younger twenties and was driven by a fear of missing out.
It wasn’t until I eventually landed one, moved in with him, that I realised not worrying about finances wasn’t a resilient foundation for love.
Plus, planning hundreds of proposals across over 30 cities, most of which I never visited, gave me a hunger for travel.
I realised I wanted to experience the world (and romance) beyond the lens of others’ relationships and wallets. So, in July 2019, I planned my last proposal and I set off to see the world as a nomad travel writer.
Now, when I have seen people getting engaged, I don’t recoil. In fact I have a newfound appreciation for this moment.
During the 2022 World Cup, I was living in Buenos Aires, and the streets went wild after the country’s penalty shoot out win against France.
Amidst an ocean of cheers and screams, a guy dropped down on one knee and posed a question to his girlfriend and I couldn’t help but stare like an idiot.
It was the first time I had witnessed a proposal happening in real life without my orchestration. And it felt like I was seeing it again for the first time sans the jadedness.
Most of all, I cherished the fact that they hadn’t thought to take a photo – that is until they noticed me gazing and approached me to ask if I would do the honours. Of course, I said yes.
This moment reminded me that, even if proposals have become more commercialised, at the heart of each one is a unique love story that can never be replicated.
And that, for me, will always be priceless.
*Name has been changed
Do you have a story you’d like to share? Get in touch by emailing jess.austin@metro.co.uk.
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