I Sent a Lookalike to Skydive With My Wife and She Didn’t Realise

In 2017, I published an article about making my garden shed London’s top-rated restaurant on TripAdvisor.

The story went viral and TV stations around the world began calling, asking me to explain how I duped people into believing that my fake restaurant was real. Little did they know, I had been tricking them too.

In a moment of madness, I sent a better looking lookalike of myself onto Australian TV. Somehow it worked, so when the BBC asked me for an interview the next week on Radio 5 Live, I did it again. This time, the guy I sent was so impressive he got follow-up interviews as me on BBC London and BBC Coventry, and still no one noticed. I had successfully outsourced myself.

While I was sitting at home playing Rocket League and analysing my FitBit statistics, the lookalikes grafted on my behalf. One model was presented with opportunities to represent Swedish products. Another was asked to go into business in India by manufacturing companies who had seen his interview on TV there. Each lookalike had specific qualities – “charming”, “smart”, “attractive” – which I utilised to suit different interviews on different stations.

This got me thinking: what if everyone could send a lookalike to do things they don’t want to do, or wish they could do better? As a bit of fun, I released an advert for an “app” that would “do” exactly this. I named it Oobah, like Uber, but also like me. You can see it here, on the “Book an Oobah” section of Oobah.com.

After being shared on social media and LinkedIn, Oobah picked up traction in the tech and funding world. I pitched it at a tech conference packed with entrepreneurs, rich people and Jakov Kitarović, husband of Kolinda Grabar-Kitarović, the fourth President of Croatia.

I was invited to Zurich to show the app off to the International Advertising Association, and was interviewed in a Swiss Sunday paper about it.

Soon, thousands of people began applying for lookalikes via Oobah.com, to find “a hot replacement for an ex’s wedding”, or someone to break up with their partner. Investors and developers started contacting me with interest.

I was in over my head.

I had no choice but to prove that my “Uber for lookalikes” app works, by answering one of the requests submitted to my app and providing them with a lookalike.

Richard is so scared of heights, he gets vertigo on escalators. Naturally, he lives the life of a pangolin: close to the ground. This has caused him some trouble with his wife, Chelsey.

It’s been Chelsey’s dream to skydive since she was a little girl, but life got in the way and money has always been an issue. Richard loves Chelsey and wants nothing more than to make this dream come true. But there’s one problem: Chelsey won’t skydive without him.

To help fix the issue, Richard asked if Oobah could provide a lookalike to skydive in his place. I said yes, and then immediately blanked out any thoughts of what might go wrong.

To recruit my lookalikes, I employed the time honoured method of walking around the streets outside the VICE office. Of the four bespectacled men I found, two could pass as Richard, while the other two could not. After a bit of thought, I chose the guy on the left, Jack.

Unfortunately, I had for some reason not explained why they were there.

“I don’t want to skydive,” said Jack, when I told him about my plan.

It occurred to me that I should have put a second question to the 50 office workers I accosted beyond, “Do you have time tomorrow?”

This left us with Guillaume, whose incredibly strong French accent was a cause for concern. Richard is English, so if Guillaume opened his mouth on the skydive, c’est fini.

I feel I should say, “To pull something like this off, you need X.” But the truth is, I’ve never pushed somebody out of a plane with a stranger before.

At its core, the plan was this: Chelsey and Richard would prepare to skydive together. They would enter the plane and, just before take-off, Richard would go to the toilet, but Guillaume would return. I then needed Chelsey to believe that Guillaume was Richard for ten minutes together while they waited for the plane to reach the correct altitude.

They would then jump out of the plane, with Guillaume landing first. We would then have 30 seconds to unclip him and lay Richard under the parachute before Chelsey landed.

It was autumnal, clear and good flying weather. I got to work on Guillaume’s makeover.

I put lifting insoles in his shoes to make him around three inches taller.

I added some “piercings” to his earlobes using magnets.

Then came a text alert: Richard and Chelsey would be there in a matter of minutes. I moved onto the likeliest thing to give the game away – Richard’s husbandly pheromones. To cover them up, Richard had been made to drink whisky since 7AM for “Dutch courage”. I sprayed Guillaume with whisky so his scent matched Richard’s, then hid him in the toilet.

Richard and Chelsey arrived, but they weren’t the only people on the sky dive.

This is Liam and Diana, a couple who were also jumping. At least that’s what Chelsey thought. They were actually two actors I’d employed to create a commotion and distract Chelsey while we switched her husband.

As we made our way up to the plane, I noticed that Chelsey was concerned for Richard. She was fussing over him, checking he was OK and not worried about the sky dive. Damn! There was no way I’d be able to switch Richard out for Guillame without her noticing. It was time for the commotion.

“I’m sorry,” Liam complained. “I can’t do this.” A scene ensued with the instructors, exactly as I’d hoped. Chelsey watched as the comrade couple did a 180-degree turn, while Richard bopped off to the toilet.

After an uncomfortable five minutes filled with lost gloves and last minute jitters, the switch was complete and Guillaume took to the runway.

Would Chelsey be able to identify the fact that the man next to her wasn’t her actual husband, but a French man? Would Guillaume keep his mouth shut? He got on the plane and the engines began to whirl.

As they took off, I ran back to the toilet and grabbed Richard. We both looked on, staring at the plane as it climbed into the sky.

“This whole thing was to get her to do this,” philosophises Richard. “And hearing about skydiving being her dream has balanced out the, ‘Oh my God, I’m betraying her.’”

Then we saw something.

Guillaume! He was about to land, meaning we had 30 seconds before Chelsey arrived from her dive. We still needed to switch Richard back in for Guillaume, which didn’t leave much time.

We ran over, clipped Richard to the instructor, and it was done.

Then Chelsey landed.

Had we got away with it? Has Richard ruined his relationship forever? He approached Chelsey.

She looked at him, then lunged.

“You did it!” Chelsey said, as they embraced and giggled in each other’s arms. “I loved it.”

“… I have no words.” Richard replied.

Chelsea struggled to contain herself, practically boiling with excitement.

“I was thinking: ‘Is he going to do it? Is he going to do it?’ I was cheering him on as he went over! I’m so happy. It was just incredible. One off the bucket list.”

I looked over at Richard as Chelsey embraced him, beaming, and realised what Oobah is all about.

It’s an app of opportunity, where in spite of all your shortcomings, you can be whoever you want to be.

It’s an app to surprise the person you love.

An app to upset the odds.

An app to make dreams come true.

WATCH THE VIDEO VERSION OF THIS ARTICLE RIGHT HERE.

@oobahs