Category: Challenging

Sort: Date | Title | Views | Likes | Comments | Random Sort Ascending

Proposal at The Summit of Mount Kilimanjaro

1.73K Views0 Comments

This guy proposed to his girlfriend in October 2012 at the top of the highest mountain in Africa, Mount Kilimanjaro. It took the couple, along with a group of other tourists, seven days to climb to the summit of this ...

Matthew’s Skurfing Proposal to Brynn

3.00K Views0 Comments

Brynn took a plunge in the ocean with her boyfriend, Matthew, clueless that this wouldn't be her biggest plunge of the day! She happily agreed to marry him after he proposes mid-skurf, and right after agreeing, the co...

Justin Baldoni’s Heartwarming Proposal at Blu Jam Cafe

2.95K Views0 Comments

Justin Baldoni, a young actor and director from LA, went above and beyond to put together an utterly incredible proposal for his longtime girlfriend, Emily. To begin with, he instructed her to meet him at Blu Jam Cafe...

Surprise Valentine’s Day Proposal on The Ellen Show

1.01K Views0 Comments

Ellen helped a viewer, Wendell, plan the perfect surprise proposal on the show. His girlfriend, Nina, will never forget this romantic Valentine's Day!

Google Maps Engagement

641 Views0 Comments

As timing would have it, The Google Map photo of this couple's home was being updated at the exact moment of their wedding proposal, and managed to catch an aerial view of it! The red car hiding out on the gravel road...

Keaton’s Fake Arrest Proposal

980 Views0 Comments

This happened on a quiet Saturday night in a small town. Keaton had his neighbor (a highway patrolman) pull him over on purpose, without Kaitlyn knowing. Keaton purposely left his valid Canadian driver's license at ho...

San Diego Airport Flash Mob Proposal

403 Views0 Comments

Ben surprised his girlfriend with this little production at the San Diego Airport (Terminal 1). She was arriving from an epic Vegas bachelorette weekend and was traveling with a group of friends. Unfortunately half of...

Not Just Another Girls Night

345 Views0 Comments

This Bride-to-be went to a theatre with her friends, thinking she was about to have a girls night. Little did she know that her boyfriend went ahead and hired a production company to put a trailer together, starring.....

Back to The Future Proposal

362 Views0 Comments

On June 21, 2009, Chanoch took his girlfriend Chani to a showing of "Back to the Future," which was being presented as part of a Michael J. Fox retrospective at a film festival in a historic local theater. In reality,...

Holt Brings Disney World to Ashley

908 Views0 Comments

When Holt realized that it was too late to propose in Disney World to his girlfriend Ashley, he decided to bring the wonderful world of Disney to her. Their closest friends and family gathered to dress up and celebrat...

Operation Julie Marry Me

676 Views0 Comments

SWAT Team member Jason decided to propose to his girlfriend Julie the only way that he knows how - by surprise operation, and with the help of a strong team. This video shows the steps that Jason took to win Julie's h...

Frankie’s Surprise Cruise Ship Proposal

336 Views0 Comments

When Frankie took Stephanie on Cruise Ship Norwegian 2013 among family and friends, she was expecting the trip of a lifetime. She had no idea that Frankie had bigger plans than she could ever imagine. On day three of ...

Darrin’s Incredible Family and Friends Video Compilation

601 Views0 Comments

Darrin reached out to every important member of Melissa's life to take part in his incredible proposal video idea. He had each person speak one or two lines of the overall proposal message that he wanted to convey, an...

Fake Raffle Win Results in Proposal Trailer Video

296 Views0 Comments

Mike told his girlfriend Kristina that he'd won a raffle for a private viewing at the local theater. Little did she know that he had created a proposal video to look like a movie trailer. Not only will you see the vid...

Mike’s Triple Surprise

270 Views0 Comments

After an uneventful birthday dinner, Mike lured Nicole back to his buddy's house, where an ensemble cast of family and friends waited eagerly to surprise her on her 28th birthday. Little did she, or any of the guests ...

Jerry’s Hot Air Balloon Surprise

200 Views0 Comments

When Natasha went for a trip in a hot air balloon with Jerry, she thought that her sweet boyfriend was taking her on a lovely, sight-seeing birthday ride. Little did she know that he was also planning on asking her a ...

Operation I-10 Proposal

182 Views0 Comments

On February 26th, 2010, Keleigh received a shocking surprise during a drive from Phoenix, Arizona to Los Angeles, California that signified the end of her nine months of long distance romance with her boyfriend. Littl...

Is He Proposing? Is He Alive?

188 Views0 Comments

One man decided to give his girlfriend a frightening proposal, as he launched himself off the side of a building in order to get his message across. We definitely don't recommend trying this at home, but it does provi...

Parachute Proposal

317 Views0 Comments

Lori DeBeri received a meaningful, funny and creative surprise while skydiving. As if the notion of falling thousands of feet through the sky wasn't shocking enough, Lori was instructed to take a glance down below, wh...

Cinderella Castle Proposal

354 Views0 Comments

Shelby received her much-anticipated marriage proposal in front of Cinderella’s castle in Disneyland!

Skydiving at Night Gets Even More Memorable

300 Views0 Comments

When Henry, a skydiving instructor, first met Karen, he promised that he'd eventually convince her to skydive with him. After nearly a year of dating, Karen finally mustered up the courage to take the plunge. Little d...

Cottonwood Man Proposes to Girlfriend in Helicopter

260 Views0 Comments

Morgan McCarley thought that she was going for her first helicopter ride, but what she didn't know was that her boyfriend, Kelly Gustafson, had chartered the chopper through a friend, and had seventy family members wa...

Proposal Using Bedsheets

255 Views0 Comments

Clifton Smith used forty-two bed sheets to spell out his proposal on his girlfriend’s family farm. The sheets were used to construct fifteen-foot tall letters, stratagically placed together on the field. In order for ...

Artistic Love Anagram

328 Views0 Comments

Industrial designer George spent 24 hours constructing a proposal art piece that he dubbed "My Early Muir Owl", which just so happens to be an anagram of “Will you Marry Me?”. George hired an artist (aptly named "Serg...

Private Theater Proposal

235 Views0 Comments

Gennady Zaleskiy played the lead actor in the stage show "The Romantics". He invited his girlfriend and friends to come watch the show, but little did they know that this would be no ordinary performance. He appeared ...

Tom Cruise Lends a Hand to Joao

191 Views0 Comments

Cameraman Joao Martins enlisted the help of a friend in order to propose to his girlfriend, Sonia. It just so happened that this friend was Tom Cruise! Joao's (Tom's) proposal aired on RTP-TV in Portugal, with Cruise ...

Don’t Skip This Commercial Break…

903 Views0 Comments

Whipping up a creative marriage proposal is challenging enough as it is, but Rand added "costly" and "team effort" to his master plan. In order to fund his one-of-a-kind marriage proposal to his girlfriend of five yea...

The Human Torch Proposal

179 Views0 Comments

Melissa was in shock as she witnessed her boyfriend Todd literally lit in flames. Thankfully, this was merely a stunt that he had pre-planned with the help of human torching expert, Eric Barkley. While engulfed in fla...

Halo 3 Proposal

170 Views0 Comments

On November 3, 2007, MMORPG player "Moviesign" made a forge map of Halo 3, where he virtually proposed to fellow gamer and girlfriend of two years, "Furtive Penguin". "Moviesign" led his lady toward a location where h...

UCLA Flash Mob Proposal

363 Views0 Comments

Trang and Nam first met on the campus of UCLA, which made it the natural choice of venue for a surprise flash mob marriage proposal!

Flash Mob Highline Proposal

452 Views0 Comments

Converging (from separate locations) on one meeting point, the families of Dodd and Alix united to form a heart, using umbrellas. At this point, Dodd took out the ring to propose to Alix. Well thought-out and masterfu...

Santa Claus Proposal

200 Views0 Comments

Santa flew from California to Nebraska to surprise his girlfriend with a proposal that she will never forget! He came bearing gifts for everyone, with the best gift saved for last! "Ho ho ho" was followed up with "yes...

Paparazzi Proposal

196 Views0 Comments

Andy surprised his girlfriend with a paparazzi shoot style proposal idea in the heart of New York City. His girlfriend was in an utter state of shock!

Isaac’s Surprise Lip Dub Proposal

243 Views0 Comments

On Wednesday, May 23rd, 2012, Isaac had his girlfriend come to his folks' home for dinner. When she arrived he had his brother sit her in the back of a car and provide her with headphones. He told her that he'd be pla...

News Anchor Proposes on Live TV to His Interviewed Guest!

205 Views0 Comments

Mark Rivera of WAND-TV went off script while interviewing co-anchor Alissa Groneninger about her role as a journalist for The State Journal Register. On national TV, he bent down on one knee and popped the marriage pr...

Bungee Jumping Proposal

212 Views0 Comments

One man gave entirely new meaning to the term "taking the plunge", by proposing to his girlfriend during a bungee-jumping adventure.

Romantic Proposal at Brownie’s Beach Boardwalk

375 Views0 Comments

With the help of family and friends, Brandon delivered a unique and romantic proposal to Rebekah. While walking down the boardwalk, she was greeted by family and friends. At each "stop" she was handed flowers that she...

Street Magic Proposal

190 Views0 Comments

Herwin's surprise marriage proposal to his girlfriend Sonia on the streets of Southampton was nothing short of spectacular. Using famed street magician Roger Lapin to help plan the event and incorporate some magic int...

Fake Photoshoot and Interview Proposal

211 Views0 Comments

Chizzy tricked girlfriend Sarah into believing that she was picked to be interviewed and photographed for the inaugural issue of a new magazine. Chizzy enlisted the help of a friend to make the scene as realistic as p...

Epic Proposal at Mammoth Falls

246 Views0 Comments

This man chose to provide his lady with not only the surprise of a lifetime, but the backdrop to match. The falls provided a romantic scene that she is sure to remember forever.

Page 1 of 21