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5 Times Celebrity Marriage Proposals Didn’t Go to Plan

Marriage proposals are supposed to be picturesque moments. Especially for celebrity couples. A proposer on a bended knee. A light breeze. A perfect sunset. The perfect celebrity engagement ring.

But proposals don’t always go as planned. Not even for A-listers.

Even the best laid plans, meticulously organized with all the money in the world and sparkling diamonds, cannot always buy the ultimate fairy-tale moment.

In fact, some celebrity marriage proposals have been downright disastrous, but just like a Hollywood film, most have a happy ending. At the very least, they make great stories for the grandkids (or the interview sofa).

We’re going to take a trip down memory lane and walk you through a few of our favorites.

GEORGE AND AMAL CLOONEY

Source: @Amalclooneyofficial1

There was a time (and a long one, at that) where the smart money was on George Clooney being an eternal bachelor. In fact, Clooney once made a $10,000 bet with Nicole Kidman and Michelle Pfeiffer that he would remain both unmarried and childless until he was 40.

George won that bet.

So, while George and Amal Clooney may now be one of Hollywood’s favorite couples, George being married at all seems impressive given his relationship history.

More impressive than his proposal, to be sure.

That’s right, George Clooney also had a rough go of it once he decided to pop the question to then-girlfriend Amal Alamuddin.

Here’s what happened.

George hid the engagement ring in an unmarked box and planned to surprise Amal during a home-cooked dinner. He had music all timed up and everything set up. All systems go.

Right before he was ready to propose, Amal gets up to do the dishes, which according to George, wasn't something she ever even did. “What are you doing?,” Clooney asked.

She returns to the room where Clooney lets her know he’s blown out the candle. He directs her to the box behind her, where the ring is. He says he thinks there’s a lighter in there so that she’ll pick it up and open it. Alamuddin opens the box, sees the ring and pulls it out.

“It’s a ring,” she says plainly. As if someone else had just left it there, and it was no big deal.

George dropped down on one knee to make the occasion just a little clearer to Amal, who was too surprised to register what was happening.

Clooney claims the playlist he had set up was nearly 25-minutes long, which is how he remembers the duration of his awkward proposal that probably felt more like an eternity. He joked that he could throw out his hip “pretty soon” if he didn’t get an answer.

As you probably already know, Alamuddin did eventually say yes. The Clooneys remain happily married Hollywood royalty and have had two children, twins Ella and Alexander.

MATTHEW MCCONAUGHEY AND CAMILA ALVES

Source: @Camilamcconaughey

Matthew McConaughey had it all planned out.

In 2011, he decided he was going to pop the big question to then-girlfriend, the Brazilian model Camila Alves. And he was going to have an audience.

McConaughey’s plan was to propose to Alves on Christmas Day in front of his entire family.

Matthew decided to box the ring several times over. He had the ring buried about eight boxes deep as if it were a nesting doll. The suspense! Alves would need to open box after box to get to the ring eventually.

Finally, once it was Alves’ turn to open her gift, McConaughey motioned for his family’s attention so they’d all be tuned-in to the big moment.

Upon Alves unboxing and discovering the ring, McConaughey dropped down to one knee and asked if she would marry him and take his name.

McConaughey didn’t reveal what Alves’ original response was, but it wasn’t a “yes.”

Although the tense and awkward moment didn’t last long, there was a brief moment when the family started to worry that Camila was going to say no.

Yikes.

McConaughey light-heartedly pleaded with Alves and told her he would stay down on his knee for as long as it took.

Ultimately, she said yes, apparently, without regrets. The happy couple wed in 2012 and remain so today, eight years later.

PETER FACINELLI AND JAIMIE ALEXANDER

Source: @Jaimiealexander

Peter Facinelli, whom most will remember from either Can’t Hardly Wait or Twilight depending on their age, decided to go with a traditionally extravagant proposal. A fly-by.

But it’s one thing to plan something so ambitious and another to pull it off. Facinelli handled the former well enough, but the to-be bride doesn’t always cooperate in a way that sees the plan off without a hitch.

Facinelli took then-girlfriend Jaimie Alexander to the top of the Empire State Building one afternoon with a scheduled fly-by at 4 pm. The plane would have a banner attached to it that read, “Will You Marry Me?”

Alexander and Facinelli arrived at the top of the building with a little time to spare.

Maybe that was the problem.

Around 3:55 pm, Alexander decided she was chilly and wanted to head inside. So, she did.

Moments later, there was the plane!

Facinelli panicked and ran inside to get Alexander’s attention. “You’ve got to come see this!,” he exclaimed. But, when the couple got back outside, the sky had become just cloudy enough to lose the plane on the horizon.

Fortunately, Facinelli had brought a pair of binoculars along. Using these, Alexander was able to spot the plane and ultimately said yes.

Unfortunately, the pair wound up breaking it off about a year later, which maybe goes to prove the long-standing theory that timing really is everything.

LL COOL J AND SIMONE SMITH

Source: @Sislovespurple

American rapper, record producer, actor, author, and entrepreneur LL Cool J, is known for his 90’s hip hop and R&B tunes, and more recently as James Todd Smith (Cool J’s real name), in NCIS: Los Angeles.

Cool J and his wife Simone Smith have now been married for 25 years. They were high-school sweethearts who wound up tying the knot, having children, and are clearly in it for the long-haul, which warms our collective hearts and galvanizes our faith in the institution of marriage.

Time flies, but we’ll never forget how they got here. Their storybook marriage came to be in a surprisingly unceremonious manner.

While the proposal itself wasn’t exactly bungled or disastrous, it was unconventional, to say the least.

Although he had mulled it over for several weeks, James Smith had no real plan at all. He didn’t even have a ring! The kicker? He didn’t even formally ask Simone to marry him.

James and Simone were cruising along in his Jeep when James popped the question.

Except, the question wasn’t “Will you marry me?”

It was, “Do you wanna do this?”

It probably wasn’t the way Simone envisioned being proposed to, but it worked.

In a way, it was perfect. The Smiths have never really been about the glamour and glitz. They wed in a private ceremony at their New York home.

The Smiths remain happily married in 2020, and we hope it’ll stay that way for another 25 years.

AIDY BRYANT AND CONNOR O'MALLEY

Source: @Aidybryant

Back in October of 2016, SNL star Aidy Bryant returned home from work, where she was greeted by the couple’s dog wearing a bowtie. Bryant recalled her bewilderment in an appearance with Seth Meyers, wondering where the dog was heading and what the occasion was.

Shortly after she shut the door behind her, O’Malley came racing around the corner with a frantic marriage proposal. He didn’t get down on one knee. Conner didn’t even have a box. He just stood across the room, holding the engagement ring and asked Bryant if she would marry him.

Bryant couldn’t tell if O’Malley was serious or not. She asked him several times.

“Is this a joke? Are you doing a joke?”

But, O’Malley was serious. And once Bryant was finally on the same page, after what were undoubtedly some awkward moments, she graciously accepted his proposal, and the two got hitched.

O’Malley and Bryant recently celebrated their 2nd wedding anniversary and remain happily married today. We like to think the dog still has his or her bow tie on, too.

BUNGLED PROPOSALS CAN BECOME HAPPILY-EVER-AFTER'S

When it comes to proposing to a significant other and getting hitched, celebs have proven time and time again that they’re no different from the rest of us.

Even the most carefully-crafted proposal plans can all go down the tubes if something unexpected happens.

What we’ve learned is when you have a rock solid foundation in your relationship, even a bungled proposal can’t derail your future together.

The most grandiose and extravagant proposals that hit the bullseye and go according to plan never guarantee happiness or a successful marriage. It takes two to tango, and marriage is a partnership.

It’s comforting to know that stumbling out of the gates doesn’t mean you’re doomed to fail.

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