Wigs, disguises, fake plane tickets: How I pulled off an epic surprise proposal


It was a “Perfect Situation” for these Brooklyn lovebirds, when a surprise proposal seven months in the making came to fruition — at a Weezer concert in Forest Hills Stadium.

Matt Leabo arranged for his girlfriend Jessica Masters’ parents to fly in secretly from Michigan and attend the concert along with four of their friends in wigs and disguises, sitting only a few rows behind them, and reveal themselves the moment after he popped the question.

The Prospect Lefferts Garden resident’s bride-to-be had no idea any of these “Only in Dreams” engagement shenanigans were going to happen at the July 12 show.

“I did not see them at all,” Jessica, 36, told The Post.

Matt, 40, said the disguises were key to the surprise’s success: “I was getting pictures of people in sunglasses — and I’m like, ‘that’s not enough.’ ”

Jessica — whose master’s thesis from Queen Mary University in London was ironically titled “The Demise of Chivalry” — said she had “nothing but happy feelings” about having her family and friends be present for her very public proposal.

However, Matt admitted he was freaking out the entire morning on the way to the show.


Surprise Weezer proposal
Can you spot the wigs? Matt arranged for Jessica’s parents and friends to attend the concert in disguise.
David Spector/NY Post

“I made it this far, up until then I was so not nervous until I got there,” he told The Post. “I kept having nightmares the ring would fall out of the box.”

Matt stored Jessica’s engagement ring, an heirloom given from her father Dean that originally belonged to her great-grandmother, in a box he handcrafted out of oak honoring their beloved late dog, Skippy.


Matt Leabo Jessica Masters
Matt Leabo proposed to his girlfriend Jessica Masters at a Weezer concert in Forest Hills Stadium. The Post has reached out to Weezer’s reps for comment about supplying the live soundtrack for this elaborate surprise proposal.
Courtesy of Matt and Jessica

Matt said he considered keeping the ring safe and delivering it to Jessica to be Skippy’s “last mission.”

“I was coating that box [with shellac resin] the morning of, with three fans on it,” Matt said. “I was like, ‘Oh man, I don’t want it to smell like turpentine when I pull this ring out.’ “

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Once everything was in place, Matt knew he had to finally ask Jessica the big question.


Skippy's urn.
Matt crafted an urn for Skippy that would first be used as a ring holder for Jessica.
Courtesy of Matt and Jessica

NYPICHPDPICT000014478652
Matt and Jessica’s beloved dog Skippy passed away while Matt was completing his master’s degree.
Courtesy of Matt and Jessica

“I’m sitting there and I’m looking to my left and right and everybody is staring at us and have their phones poised,” Matt said of the moment of truth.

When Matt first started proposing, Jessica didn’t notice and was annoyed he was talking over her favorite song from opening band Future Islands.

“I was like, ‘Why are you trying to talk to me now?’ ” she recalled with a chuckle.

But Matt eventually got through to her — and Jessica said yes!

That’s the moment when Jessica’s parents and friends all removed their disguises and rushed over to a shocked Jessica, as a delighted crowd of onlookers applauded.


Dean and Jeri Masters
Jessica’s parents Dean and Jeri flew to New York in secret to surprise her.
Courtesy of Matt and Jessica

Jessica was completely blindsided, “He was dropping some major hints he was gonna propose — but I had no idea it was gonna be at the concert,” she said.

The Post has reached out to Weezer’s reps for comment about supplying the live soundtrack for this elaborate surprise proposal.

‘An expensive no’

Matt first got the idea for the surprise proposal back in January when he was in “the nightmare process” of completing his master’s degree in industrial design from Parsons University.

“I gotta propose at the end of my semester because I put her through a lot of stress, I was under a lot of stress because of my thesis,” Matt said of his thinking at the time.


Dean Master's
Dean said not giving his permission would have been “an expensive no.”
David Spector/NY Post

Matt chose Forest Hills Stadium as the location since that was the spot where the couple had first officially met.

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“I like the full circle in my narratives,” Matt said.

Meanwhile, once Matt knew when and where he was going to propose, he realized he’d first have to ask her father Dean, a retired major in the US Air Force, for permission, since it was “very important” to both Jessica and her dad that he do so.


Phony plane ticket
Matt even went so far as to Photoshop a phony plane ticket to throw Jessica off the scent.
Courtesy of Matt and Jessica

Matt decided to surprise him, too.

“Matt asked me at the end of February, Dean wasn’t in the loop til June 2nd,” said Jeri, Jessica’s mom, “I’ve never lied so much in my life,” she added.

“We share everything,” Dean chimed in.


Matt and Jessica
Matt said the urn took 3 weeks to complete.
David Spector/NY Post

However, that plan almost fell apart at the beginning of this elaborate love scheme.

Jessica was extremely “homesick,” Jeri said, and hadn’t seen her parents in over a year. She also had use-or-lose vacation days she needed to max out.

“I was lying to Jessica about the date of my mother’s surgery so she wouldn’t come home,” Jeri said.

“That was hard in the moments when she was really missing her parents,” Matt admitted.


Matt Leabo Jessica Masters
Matt said delivering the ring to Jessica was Skippy’s “last mission.”
David Spector/NY Post

When Matt flew to Michigan to ask Dean’s permission, he told Jessica he would be going to Los Angeles to work on a puppet show, and even Photoshopped a fake plane ticket and hotel itinerary to mislead her.

Dean was elated when Matt showed up at his home unannounced to ask his permission to marry his daughter.

“To me, that was a fantastic thing, we hugged and I gave him permission,” Dean said, “I [couldn’t] say no, that would be a very expensive no.”

The full circle

After seven months of laborious planning, flying across the country on false pretexts and wood carving, the entire proposal almost fell apart at the last second.

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Jessica and Matt
Jessica said she felt “nothing but happy feelings” about the surprise proposal.
David Spector/NY Post

Jessica Master's
Jessica’s engagement ring originally belonged to her great-grandmother.
Courtesy of Matt and Jessica

“The day of she’s like something’s happening. She’s texting my other friend. ‘Matt’s acting weird he’s either gonna propose or cheat on me,’ ” said Jessica’s friend Katharine Bray, a Rockland County nurse.

Thankfully, Jessica was able to be convinced that if Matt was going to propose he would most likely do so at his upcoming graduation party, and the plan went off without a hitch.

Katharine was overjoyed to see the proposal, which was so long in the making, come together so smoothly, “for plan A to work was amazing,” she said.


Jessica and Dean
Matt said the parents reveal was the “icing on the cake.”

“The icing on the cake was the parents reveal, which I was so nervous about, that was the moment I was the most elated was seeing her reaction to her parents,” Matt said.

For Jessica, the idea of a public proposal had originally seemed daunting to her.

“It was a little more intimate in my head,” she admitted.


Jessica and Matt
Jessica and Matt embrace during Rivers Cuomo’s acoustic performance of Pinkerton classic song “Falling for You.”
David Spector/NY Post

Jssica and Matt
Matt says he hopes to one day trick his fiancée Jessica again.
Courtesy of Matt and Jessica

But Jessica was thrilled by the way it all turned out in the end.

“I was so excited to have our closest friends and family there and I think that was one of the best concerts we ever went to for many reasons it was such a great experience,” she said.

“I was overwhelmed but so, so excited, so happy.”

The pair have not yet set a wedding date — and this may not be the last trick Matt has up his sleeve.

“In five or ten years I wanna get her again,” Matt said mischievously.



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