This proposal was different than any other I’d done before. 

Jorge reached out with this great idea:

Frame this like a “run of the mill Groupon scavenger hunt”.  Slowly but surely, we’d start twisting the adventure to become more and more personal until it ended with the knee drop! Envelopes would change from referring to them as “The Historians” to eventually using their real names. Things would start very simple and superficial, but eventually be very personal.

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Prep work: 


I arrived in Pittsburgh a week and a half early.  I always prefer to give myself this much time so I can check locations a week and a half early (Nothing is worse than learning there is a massive farmer’s market the day of your adventure.) I was able to meet with Jorge a few times and even do a dry run of the actual proposal in front of St. Mary’s of the Mount Church on Mt. Washington. (*Note* If you’re going to propose, I STRONGLY recommend doing this.  It helps to be able to inform the photographer of angles, framing, and logistics). 

Next, we touched base with the family! They were excited and on board! Clara’s mom came up with the decoy idea. She knew that if this seemed too legit, Clara would probably Google it.  So we told her that a friend of a friend was starting a business creating scavenger hunts, and their family would be split in three groups and test out three different adventures!

The Morning of the Adventure day.

I met with Clara’s mom in the morning. She gave me the ring which went directly into the locked chest.  I gave her the starting envelopes and the GPS tracker for Jorge. Then I met with Jon, my agent for the day, and Sandra, (The world’s best photographer) at Market Square and we waited….

My GPS alerted! They’re on the move, heading to the first stop!

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Phase One:

The premise of this adventure was simple: George Washington was stationed at Fort Pitt and had left behind an heirloom.  They needed to find a descendant, get the chest containing the heirloom, and then find the key to open said chest. 

The first instructions: Find the payphone in Market Square.  Once they lifted the phone, there was a tiny envelope instructing them to a nearby bar, NOLA on the Square.  They sat down at the bar and said “We’re looking for Mr. Washington.” The team at NOLA on the Square was amazing.  “everything has been paid for, what would you like to drink?”

They had a drink and were given an envelope with the next instructions: Find the oldest building in Pittsburgh. 

Can you spot the envelope?

Can you spot the envelope?

Once they’d finished their drinks, they headed off to the Point Park Blockhouse. Once there, they located the next envelope fastened to the gold cannon outside.  The envelope contained two tickets to the museum and a cipher.  Once they decoded the cipher, it sent them to a cannon which pointed to a location outside.  

They followed a compass and took steps to meet the “Descendant of George Washington!”  He handed them the chest (secretly containing the ring) and a key! Unfortunately, that key didn’t fit!

But they knew where to go next!

They headed to Robert San Clemente bridge.  Right in the center, was a lock just for them. 


They popped the lock and there was a little note. This sent them to Captain Mike with Revertive Recreation.  They got to the boat, and off they went! Captain Mike took them to Station Square.

As they disembarked from the boat, they were handed another envelope containing tickets up the Monongahela Incline.


Phase two

At this point, instructions started to become more personal (let’s be honest, once she got on a boat, she HAD to know something was afoot).  Instead of being referred to as “The Historians,” Envelopes were made out to “Jorge and Clara”.  The wax seal was also changed from a compass to a “C”. 

Once at the top of the incline, they followed the instructions to Coughlins Law.  This awesome bar and brewery up on mt. Washington. Same as before, they used a password, had a drink, and figured out where to go next!


After a quick walk, they reached their next location: Love Pittsburgh.  Inside the shop was a change of clothes (they’d been walking around half the day and they needed to be in nicer attire for the big moment).  The change of clothes was put in so they could “blend in at the next location” (in truth, no one wants to look gross and sweaty during a proposal). They had one last envelope to find on an overlook. Then they headed to the big moment. They walked to the church, found the key hanging from the Eagle’s neck, opened the chest, and the rest was history! 


Notes if you’re going to propose:

  • Hire a professional photographer. Your cousin’s friend who is in photography school is not the same as a pro photographer who’s willing to crouch in the corner or hide in the bushes for the perfect shot.

  • Do a dry run of the actual moment (especially if you’re going to be with your future fiancé).  This helps you figure out things prior to the moment.  Because in that moment, your heart will be beating out of your chest!

  • Coordinate with businesses and restaurants in advance. They LOVE these things. I know it can be a bit nerve wracking reaching out to them, but it’s VERY worth it.

  • Bring an extra helper into the fold. I don’t care if this is your best friend or someone you’re hiring. Best case scenario: you won’t need them. But when push comes to shove, you’re going to be REALLY glad you have someone available to sprint to a store to pick up a bottle of water or run home and grab the ring that you accidentally left in your sock drawer.