The 15 Most Awesome (and over the top) Marriage Proposals | Chi-town Brides
The 15 Most Awesome and over the top Marriage Proposals Chi Town Brides

The 15 Most Awesome (and over the top) Marriage Proposals

Proposing marriage is one of the most significant moments in a couple’s relationship- filled with nerves, excitement and an element of surprise. However, we’ve seen quite the movement away from simply getting down on one’s knee. With everything from artful expression to choreographed routines, those asking are finding more and more outrageous ways to showcase their love. In recent years, these wildly entertaining and boldly romantic have not only been recorded but broadcasted as inspiration for romantics everywhere. Check out these 15 over-the-top proposals that taking popping the question to a whole new level!

1. The Moving Car

In this heartwarming clip, Isaac invites his girlfriend to meet at his parent’s house for dinner. When she gets there, his brother invites her to sit in the trunk of an open car and gives her a pair of headphones telling her Isaac “wanted to play her a song.” As the lyrics to “Marry You” by Bruno Mars begin playing, the car starts moving and the performance begins! Over sixty friends, family and high school band members dart in and out of the street to a choreographed routine. At the close of the song, the car comes to a stop and they clear a path for Isaac. When he finally asks Amy for her hand in marriage, the emotion is overwhelming!

2. The Graffiti Wall This time lapse shows an artistic approach to engagement. Over the course of several weeks, Jeff develops an intricate wall mural with a hidden message. He paints a personalized canvas featuring her mom’s dog Parky. As Caitlin is coming to meet Jeff, she sees the “Will You Marry Me?” message spelled out on scrabble tiles (the couple’s favorite game!)

3. The On Air Proposal This local Alabama newscaster actually broadcasted her own proposal before it happened. Jillian begins reading her teleprompter but instead of the scheduled news, the message is that she’s about to be proposed to! Her fellow cast members clear off screen, and her fiancée comes out and gets on one knee on live TV! She and the rest of Hunstville got quite the surprise that evening.

4. The Fake Out Proposal So Jordan had his proposal to Summer all planned, but when she found out in advance, he had to change some things around. Instead he creates a series of fake outs throughout a night of their favorite things. Before leaving the house, he gets downs on one knee- but only to tie his shoe. At the dinner, he stands and makes an announcement to the restaurant- but only to say it was the site of their first date. After dinner there is an acoustic performance outside the coffee shop they often walk to, but still nothing. The build up makes the actual proposal even more romantic than anticipated!

5. The Peter Pan Proposal Talk about an on stage romance! Lilly-Jane received quite the surprise during a performance of the musical Peter Pan in her hometown of Glasgow. She, playing Wendy, was caught off guard when Peter, played by her boyfriend Sandor, and the rest of the ensemble stopped mid-song. Sandor interrupts the entire performance to ask her to marry him on stage! He ensured her family was in the audience as well, making for quite the magical evening for everyone involved!

6. The In Flight Proposal Chicago pilot Ryan Thompson played quite the trick on his fiancée, Carlie before popping the question. He took her for (what she thought was) a quick ride to view the Chicago skyline. Midway through the flight, Ryan tells Carlie the plane is experiencing a serious malfunction and asks for the emergency instruction manual. As plane appears to be losing control, Carlie reads the manual to say, “Ring Engagement Procedure.” She continues to read clever queries like “Determine if he is a good mate,” and “He will always love and honor you,” all under the impression these words will prevent a plane crash! Although they were never in danger, the emotions definitely run high before this engagement!

7. The Global Proposal This proposal spans 26 countries over the course of 4 years. Jack knew from freshmen year of college that Rebecca was the one, and took the time (and miles) to tell her. He lip-syncs the words to “I’m Gonna Be (500 Miles)” by the Proclaimers across China, Greece, France and beyond. At the end of their college career, instead of the graduation video she thought she was watching Rebecca is surprised by Jack’s global- inspired proposal!

8. The Home Depot Proposal When imagining romantic proposal locations, Home Depot isn’t the first place that comes to mind. Dustin entered shopping for some new lights and instead came across this over-the-top marriage proposal! After being redirected, he comes across a flash mob of his family and friends (including many on laptops and iPads!) The aisle fills with a choreographed performance to “Somebody Loves You” by Betty Who. At the end, Dustin’s boyfriend appears in a suit ready to ask him for marriage.

9. The Subway Proposal Adam and Lucy were riding the subway, when a rather unusual performance came about. The passengers began singing Lucy’s favorite song, “Lovely Day” by Bill Withers. It turns out that Adam gathered members of his choir to sing as he asked her to marry him underground. He and the choir had only three minutes to pull the whole thing off- talk about nerve-wracking!

10. The Harry Potter Proposal. For fans like Jayson and Andrea, a Harry Potter scavenger hunt is fun- but what about a Harry Potter- themed proposal? The adventure began when Andrea received a sealed envelope from a cameraman at her door. It contained a quest of clues leading Andrea to her favorite places around town. At the end of the journey, Jayson was waiting at a candlelit table inside her favorite bar. After a series of books inside of boxes for her last leg, he got down on one knee and proposed!

11. The In Flight Proposal What better way to propose to someone you met on a plane, than on a plane! Arvin and Alexandra met on LaGuardia-bound flight and in 2010, and would engage to be married years later on the very same flight. Delta provided passengers with champagne as Arvin got on the loud speaker to broadcast their love story and ask Alexandra to marry him. So much better than an in-flight movie!

12. The Bulls Proposal We’ve seen proposals at sporting events, but not usually mid-court! This Chicago Bulls’ Luvabull cheerleader was in for quite the surprise during this game versus the Miami Heat. In the middle of the squad’s performance, the choreography suddenly switches to a routine with which Ariana is not familiar. Instead, the team’s mascot sits her down in a rolling chair as the performance continues around her. When Bruno Mars’ “Marry You” begins playing, her boyfriend, Shane pops out of an inflatable “Bennie the Bull,” and asks for her hand in marriage, center stage!

13. The Flash Mob Proposal When Dave took his girlfriend E for a walk through Times Square, she would have no idea what was in store for her. First the couple comes across a microphone and Dave proclaims his love, but it doesn’t stop there. Next, the couple enjoys a live performance of E’s favorite song as a flash mob is preparing the performance of a lifetime behind them. Slowly but surely individuals begin dancing, until Dave is leading the entire mob in a routine, all for E. At the close, they hold up the message reading “Will You Marry Me?” and Dave gets down on one knee.

14. The Movie Theatre Proposal What happens when an on screen love story comes to life? Ginny thought she was in a normal night at the movies with her brother because Matt was “at work.” In the midst of the trailers before the “Fast 5” movie, Ginny hears a familiar voice. She instead sees Matt asking her parents for permission to marry her and then making his way to the movie theatre. As the video takes the viewers right to the movie theatre doors in real time, Matt appears in person for a romantic proposal, that truly rivals the movies!

15. The Ultimate Proposal For the most elaborate of the over-the-top wedding proposals, meet Justin and Emily. Emily arrives at a café, prepped with candles and quite the romantic ambiance. A video starts playing in which Justin tells her is proposing, but not for 25 more minutes. Over the course of those 25 minutes, he (with the help of some friends) performs for her in several different ways. After everything from N’ SYNC to ABBA, Justin leads her to a flash mob, followed a montage of their most special moments. He even incorporates his parents towards the end, including their approval in the video. With all of the (humanly possible) romantic elements in place, Justin delivers his heartfelt proposal and she accepts, all in the location of their very first date!   After the proposal, check out these 10 Unique Locations in Chicago to take the creativity into your engagement photos too! Now is when the planning begins- get your engagement started by pursuing some Wedding Styles and gather the next inspirations for the big day.

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