Top 10 Cutest Celebrity Engagement Stories

This pair of dancers may be a little less well known than some of the other celebs on our list today, but their story merits inclusion because it’s just so darn sweet. tWitch is an actor and dancer that you may recognize from “So You Think You Can Dance”. When he wanted to propose to his girlfriend, dancer Allison Holker, he tried to do it in the most surprising way possible. They were both booked to shoot a commercial for Microsoft and he popped the question on set while all the cameras were already on them, inviting her family to watch.
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After starring in so many romantic comedies, it’s no surprise that this actor knew how to execute the perfect proposal. Rather than doing something showy or over the top, he decided to have the big moment take place at home on Christmas. But he wasn’t above making his bride-to-be wait a little. He wrapped the engagement ring in a box inside a box inside a box (and quite possibly a few more boxes). Since their family tradition is taking turns to each unwrap one present, she had to wait until the very end to finally see what had been hiding within all the packages. And then… she made HIM wait.

Not everyone wants a big public proposal, but if you do… then this one might just be the gold standard.. “Dancing With the Stars” regulars Maksim Chmerkovskiy and Peta Murgatroyd (better known together as Maks and Peta) met in 2009 while working on Broadway, and begin an on again, off again relationship in 2012. Since dance is clearly such a big part of this couple’s lives, Maks decided to ask for Peta’s hand during a performance of the show they were both working on, “Sway”. The crowd went absolutely wild when they finally realized what was going on!

Considering what we know about these two A-listers, does it come as a surprise that their proposal story is over the top? Considering this wasn’t going to be Kim Kardashian’s first marriage, Kanye West pulled out all the stops to ensure his proposal was a cut above the rest. On Kim’s 33rd birthday in 2013, Kanye arranged an exclusive rental of AT&T Park in San Francisco but he had no interest in watching a ballgame. He had invited all of Kim’s friends and family who were hiding in the dugouts before the big reveal. He eventually pulled out a ring box while the jumbotron read “PLEEEASE MARRY MEEE!!!”.

Sure it’s nice to get engaged while surrounded by your friends and family, but popping the question when you’re on vacation in an exotic locale is a nice alternative. And that’s how Jose Antonio Bastón did it when he asked Eva Longoria for her hand. The two were in Dubai in the desert and Longoria says she was Snapchatting everything in sight because their surroundings were so beautiful. She soon got an inkling that something was up however and put her phone away. Thankfully, her intuition was spot on! Bastón popped the question while they were surrounded by animals and drinking champagne. Honestly, we kinda wish she HADN’T stopped Snapchatting.
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This is one couple that prefers to fly under the radar, and their proposal story is just as sweet and simple as their relationship. During an appearance on “Live with Kelly and Michael”, Joe Manganiello dished on how he went about proposing to girlfriend Sofia Vergara - and it sounds like it was the perfect intimate moment. Considering her Colombian roots, he wanted to impress her by proposing in Spanish rather than his native English. He says he wasn’t worried about her rejecting his offer, but he was anxious about messing up the speech he had prepared. So cute!

One day while Neil Patrick Harris and David Burtka were in a limo on their way to an event, Burtka insisted they make a quick stop. Why? He wanted to propose to Harris on the street corner where they first met. How romantic is that? Then, roughly a year later, Neil Patrick Harris proposed to Burtka! Choosing to keep it private for years, the couple finally informed the world 5 years later in 2011 in celebration of gay marriage passing in New York. In 2014, they finally tied the knot. It seems like it was all worth it though because they were wed in Italy with Elton John performing at the reception.

Never one to stick to conventions or adhere to expectations, it’s no wonder Pink decided to do things a little differently when it came time to make a commitment to then boyfriend Carey Hart. Rather than let him do the asking, she decided to take things into her own hands. While Hart was participating in a motocross competition, Pink made a sign that read “Will you marry me” which she held up on the sidelines. On Hart’s second lap, he parked in front of Pink, abandoning the race in order to accept her proposal. Now that’s a pair of people truly meant for each other!

Mr. Robot creator Sam Esmail is a writer and director who clearly put his creative skills to use when it came to proposing to girlfriend, actress and singer-songwriter Emmy Rossum. The two habitually read the New York Times “Modern Love” column when it’s published each Sunday, but one week the tradition became a little more special. Esmail created a mockup of the column and gave it to Rossum while she was in the bath. It took her a moment to realize that this story was about a director and and actress who bore a striking resemblance to her and Esmail. How cute is that?

Grab the kleenex, you’re going to need it for this one. Considering marriage is all about creating a family, Dwyane Wade had the right idea when he decided to involve his right off the bat. Wade and his two sons were spending the day with Gabrielle Union checking out the construction on their house when the boys said they wanted to do a presentation for her. They had made a sign that said “will you marry us”. She thought it was sweet, but since they asked her to officially join the family all the time, she didn’t realize it was a real proposal. That is, until she saw Wade down on one knee with a ring box.