Boyfriend Tricks Girlfriend Into Going Wine Tasting—Then She Sees What He’s Really Been Plotting the Whole Time

It’s tradition for any guy to have “the talk” with his girlfriend’s dad when the time comes to pop the question.

A guy named Matthew Russo took that tradition to a WHOLE new level.

In what has to be one of the most thoughtful proposals floating around the Internet today, Matt planned a two-fold surprise for his girlfriend, Kristina Broughton.

Kristina Broughton

It all started when he had her drop him off to catch a flight from San Francisco to New York where he was going to “celebrate a friend’s birthday.”

What Kristina didn’t know is that his entire trip was actually to ask for her family’s blessing.

With the help of his close friends, Matt made the rounds, visiting each of Kristina’s family members and documenting the whole thing to later use for his proposal!

As tradition would have it, he started with her dad.

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Though he’d passed away nine years ago, Matt didn’t neglect to visit his grave and have a little chat.


Kristina and her dad shared a special bond, and she often made comments about how similar Matt was to him. This stop was by far the most touching.

“I wish I would’ve had the chance to actually have met you. 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,” Matt says at the grave. “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.”

From there, he and his friends headed to Orlando, Florida, to visit Kristina’s mom. She was shocked and pleasantly surprised to see Matt without Kristina.


“Her father would be so happy too, Matt,” She said. “He knows you’re good to my daughter, that you love my daughter.”

After getting mom’s blessing, Matt was wheels up one final time to Las Vegas, where he visited Kristina’s grandmother.


Speaking directly to Kristina through Matt’s camera, Grandma explained that the ring she’s about to receive—a 1935 diamond in a custom rose gold and platinum setting—has been in the family for more than 80 years!

Kristina Broughton

After making all the rounds, Matt put the video montage together and planned yet another surprise for his soon-to-be-bride.

Just a few months after his trip to New York (and Orlando, and Las Vegas), Matt took Kristina to a Napa Valley winery “to celebrate another friend’s birthday.” It just happened to be the exact winery where the couple met and fell in love five years ago. Matt tricked her into thinking she was there for a wine tasting, but of course, he had a much more extravagant plan up his sleeve.

Kristina is led to a table inside where a laptop is set up for her to watch a video—little did she know, it was her own engagement video!

Throughout the video, Kristina appears in the bottom left-hand corner, visibly emotional and touched by Matt’s grand gesture.

With friends and family gathered around, Kristina is sent outside where Matt is waiting! After months of planning and anticipation, he seals the deal by dropping to one knee!


His proposal was so thoughtful, and meant the world to Kristina. Of course, with 4.3 million views, it’s setting the bar HIGH for single guys everywhere!

Grab your kleenex and check out the whole proposal below:

Congratulations Matt and Kristina! May your marriage be a lifetime full of surprises!

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Bri Lamm
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Bri is an outgoing introvert with a heart that beats for adventure. She lives to serve the Lord, experience the world, and eat macaroni and cheese in between capturing life’s greatest moments on one of her favorite cameras.