“How To Make Your Girlfriend Cry.” Man Stages Epic Proposal That Has Us Weeping, Too!

We’ve all heard of some pretty creative proposals, but Matthew’s is by far one of the most thoughtful and romantic of them all. As one poster commented after watching his video, “This guy is now making it really difficult for the rest of us.”

On March 3, 2016, Matt had his girlfriend, Kristina, drop him off at a train station so he could catch a flight from San Francisco to New York under the guise of celebrating a friend’s birthday. Kristina had no idea Matt had a huge surprise up his sleeve.


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Kristina may have believed Matt spent that trip hanging out with friends, but in reality, he was visiting her family members ahead of his planned proposal at the very Napa Valley winery where they had met five years earlier.

With his friends in tow to capture everything on video, Matt made a surprise visit to her mother’s home in Orlando to ask for Kristina’s hand in marriage.

“Her father would be so happy too, Matt,” Mom said, after getting over the shock of seeing him without Kristina. “He knows you’re good to my daughter, that you love my daughter.”


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Matt also traveled to Las Vegas, where he paid a visit to Kristina’s beloved grandmother. Speaking as though her granddaughter were sitting directly opposite her, Grandma says the ring Matthew will give her — a 1935 diamond in a custom rose gold and platinum setting — has been in the family for 80 years.

“I’m really excited about this and I hope that you’re as excited as I am,” she says. “I want you to have as much pleasure out of it that I had, and I had it for many, many years.”

But of all the sites Matthew visited during that trip, the most heartwarming, romantic and thoughtful of all was a cemetery in Highland Mills, NY.


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Kristina’s father passed away four years before she and Matthew met, and she had often commented on the similarities between the two. Matthew knew how important her father is to his bride-to-be, so he arrived at the gravesite with a bouquet of flowers.

“I wish I would’ve had the chance to actually have met you,” he says in the video below. “Kristina tells me all the time about how you and I are very similar. I take pride in that considering how highly she speaks of you. I hope you’ll accept me and allow me to one day be your son-in-law. I promise to adopt your role as a caregiver. I promise to protect and look after your daughter for as long as I live.”


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Several months after he returned from his trip, Kristina arrived at Napa Valley’s Kuleto Estate Winery with Matthew, believing they were celebrating another friend’s birthday. Instead, she was shown the documentary-style video below, capturing everything Matthew went through before popping the big question.

Inevitably, the online community gave Matthew major props for the thoughtful proposal to his longtime love!


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Check out the proposal below (get your tissues ready), and share to melt hearts!

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