“I felt like someone had given me like a truckload of heroin to hold onto, I felt like the feds were going to kick in my door at any second. I couldn't have a conversation with my girlfriend. All I could think of was this ring.”

– Seth Rogen on proposing to Lauren Miller

For the overwhelming majority of us—the plebiscites of Earth—a “Hollywood Wedding” is a concept so alien that we afford it the same reverence as we would a place of worship. 

Before you start ululating and yelping out, “amen” and “testify”, this reverence does not preclude celebrity proposals and their outcomes from our harsh, unsolicited judgement and scorn. To this end, I have termed a new verb: rich-bashing. 

Although self-explanatory, to rich-bash is to stigmatize the wealthy, their actions, and their lifestyles. This behaviour is generally propagated by jealous, everyday pedestrians to make us feel more secure about the (comparable) poverty in which we languish. 

Don’t lose sight of the irony here: it’s the very same people performing the rich-bashing that give status to these stars, both in and out of love. Celebrity culture provides the everyday human with a means for fantasizing and escaping; it also acts as a punching bag for us to vent our life-accumulated vitriol on, far away enough from us that we can’t be blamed for causing any real damage but close enough that we still obtain a sick-but-satisfying sense of catharsis. 

To put it simply, we love to see the big guys fall.

Whether it’s a fall from grace or falling in love, you can bank on cheers and derision from society at large. In this article, we’ll take a look at crazy celebrity proposals—the good, the bad, and the downright nutty. We invite you to join us for a rich-bashing bonanza as we look at proposals so suave they make us sick, as well as times when getting down on one knee and playing it safe may have been a saving grace. 

So sit back, relax, and have your Smith & Sinclair cocktail gummies at the ready—we're about to break down the 10 most beautiful and barmiest celebrity proposals of all time. 

The All-Time Romantic Gestures

1. Ludacris and Eudoxie Agnan

 The “Act a Fool” rapper and multi-hyphenate did anything but when the time came to declare his love. 

 Luda decided to show his fiancé, Eudoxie, that love is quite literally in the air by chartering a private jet for them and their friends before popping the question thousands of feet above the ground. 

 The first-class proposal didn’t stop there: once the plane was sky-high, it was flown over a field where a pyrotechnic display spelled out the message, “Eudoxie Will You Marry Me”, over the grass. It would appear that this extravagant, unique proposal idea went down as well as it should’ve, with Luda later posting a picture of the newly engaged couple on his Instagram, captioned: “She didn’t say yes. She said, HELL YES! #milehighproposal.”

2. Orlando Bloom and Katy Perry

Even Warren Buffet-sized bank accounts can’t help the rich and famous hide from their human shortfalls! 

That’s actually what makes the Bloom/Perry engagement one of the sweetest celebrity proposals we’ve heard of. It started with dinner (a fine start), followed by promises of a trip to an art exhibition. Instead, they pulled up to a helicopter—men, take notes for some serious engagement inspiration—and what followed was equally cute and chaotic. 

Champagne was already in the helicopter (naturally, as one does), the ring was poised for presentation in Bloom’s pocket, and a note declaring undying love and commitment was waiting to be read. 

 The note was supposed to serve as a distraction for Perry while Bloom exhumed the ring from his pocket. The problem? The large ring box wouldn’t budge, causing Bloom to rip his pocket and careen his elbow into bottles of champagne. No pain, no gain: after this hiccup, everything else was idyllic, with the helicopter landing on a rooftop where Perry’s friends and family greeted the newly engaged pair.

3. Kanye West and Kim Kardashian

Although many of his antics are questionable, to say the least, one of the few arenas in which Ye managed to retain his dignity in the public eye was during his proposal to Kim K. 

Displayed on the reality star’s show, Keeping Up With The Kardashians, the rapper went all out and splurged nearly $3 million on the opulent proposal. For Kim K’s hand (one that has never been “gold-digging” before), West rented out San Fran’s AT&T ballpark, blindfolded Kim K, and led her out to a pitch (no pun intended) black baseball field—where a 50-piece orchestra proceeded to serenade her with her favourite track, “Young and Beautiful” by Lana Del Ray. 

While this was happening, the couple’s close friends and family were silently hanging in the dugouts, waiting to celebrate the lover’s next big step. “PLEEEEASE MARRY MEEE!” was displayed across the scoreboard, which signalled West to drop to one knee and present Kim with her very own finger-sized crown jewel—a 15-carat Lorraine Schwartz diamond ring—one of three he commissioned, of course!

4. Miles Teller and Keleigh Sperry

Miles Teller had no whiplash when the time came to propose to his partner, Kaleigh. 

He whisked her away to a luxury safari in Africa and masterminded one of the sincerest romantic gestures we’ve seen. He asked their game guide to tie a rose to a tree early one morning before getting Kaleigh to join him for a coffee walk along a scenic vista. 

Plot twist: She saw the rose as they walked and thought someone had died.

Unperturbed, Miles has already had the tour guide write a note there indicating that the day was, in fact, the day that they had first started dating. Miles then turned to Kaleigh and delivered this completely epic line: 

“This is the day you became my girlfriend, and today was the last day you woke up as my girlfriend.”

Now THAT’S a celebrity proposal worthy of an Oscar. 

The All-Time Romantic Jesters

1. Lauren Miller and Seth Rogan

Seth Rogan is a hilarious man, but proposing got the breast—whoops—we mean the best of him. 

We won’t be taking relationship advice from Rogan anytime soon, as it appears that the super-confident comedian suffers from the same jitters when dealing with love as the rest of us mortals. He became so panicked as the time for his proposal drew closer that all his plans went out the window, and the ring started controlling his mind. 

In fact, so heavy was the weight of the ring on his shoulders that as soon as he got it, he found himself compelled to walk right upstairs to his unsuspecting fiancé, clad in only her underwear, and, in a panic, opted to place the ring on her nipple.

Ultimately, Rogan could only say, "I didn’t picture it like this, and I know she didn’t picture it like this. No little girl is like, ‘It’ll happen in a closet with my titties out.’”

2. Jada Pinkett Smith and Will Smith

Well, at least there was no slapping involved.

Still, though, the now semi-disgraced rapper and actor truly did his best to give Jada the most unmemorable proposal ever. Smith decided to pop the question one unceremonious evening while he and Jada were lazing around in bed, on the brink of falling asleep. 

Will Smith explains, “I looked over at her, and I said, 'Hey, we might be real good married. Wassup? You wanna marry me?’”. No ring, no bend of the knee, no shame. But it worked, and Jada said yes. 

Apparently, she’s rather forgiving; just don’t make jokes about her near a red carpet.

3. Megan Fox and Machine Gun Kelly

When it comes to crazy celebrity proposals, Megan Fox must be a transformer because she keeps reappearing in them. 

Never mind her first disastrous proposal to Brian Austin Green that resulted in a 2-carat diamond engagement ring lost forever in the sands of the beach and time—things only got more bizarre when MGK entered the scene. 

In July 2020, MGK and Fox sat under a Banyan tree filled with the blind optimism that love engenders in those whose hearts it strikes. Unaware of the circus that awaited them, the two asked for magic and then proceeded to… drink each other’s blood. Unfortunately, this blood offering did not appease the god of romantic gestures, and the relationship has been bleeding out ever since. 

4. Matthew McConaughey and Camila Alves

You can’t really slate Matthew; he’s a legend with a winning smile. But we thought we’d give his proposal an honourable mention in the crazy celebrity proposal category just to show you that even the slickest among us sometimes fumble in love!

It started with a typical McConaughey family Christmas celebration where everyone took turns opening their gifts. Matt had wrapped Camilla’s engagement ring in different boxes, 8 boxes deep. When it was finally her turn, Matt excitedly called his family over. Camilla reached the ring and froze; Matt took a knee and asked her to marry him; Camilla went silent. Remember, Matt’s whole family was spectating? 

Although Matt has never revealed what Camilla’s first words were in response, we know they weren’t the sought-after “yes”. Eventually, Matt said, “Look, I’m down on a knee. I’ll stay here awhile. I will outlast you.”

He did, and she conceded. The end.

Don’t Take Relationship Advice from the Famous

From drinking blood to mile-high declarations of love, crazy celebrity proposals abound and exist as fodder for us mortals to distract ourselves with. 

When you have millions of dollars—so much money that you’d struggle to spend it in one lifetime—and then marry someone who likely has accumulated the same level of fiscal surety, making an impression becomes that much harder. 

It’s tough to find engagement inspiration when you have an exotic zoo in your backyard, you have travelled to every continent on Earth many times over, and you can afford a ticket on Musk’s SpaceX for yourself and every one of your fans. 

It’s these subtle hardships that come with a life of devastating luxury that we, the plebs, can never begin to fathom. 

Perhaps we’re lucky to remain outside of the ambit of mega-fame and wealth where love is concerned; perhaps we are wealthier than our superstar counterparts where it matters most. 

Unique Proposal Ideas with Smith & Sinclair Cocktail Gummies

Picking the perfect moment and finding absolute engagement inspiration are concepts that may just be as mythical as the unicorn. 

Love isn’t perfect, and that’s what makes it so worth it—the coming together in a communion of total acceptance. When you find that soul mate, your special person or people (whatever you’re into), it shouldn’t be about the ‘where’ and ‘how’ of the proposal; it should be about the intention in totality. 

No matter how you decide to pop the question, we have a suggestion that will add colour, zeal, and joy to the occasion: our Smith & Sinclair Cocktail Gummies. Take your beloved to a place you both find beautiful and make the memory an indelible one with our tasty treats that are unforgettable once devoured. 

There’s also nothing like a little Dutch Courage prior to a pivotal life moment, such as a proposal, to make it a romantic gesture without the sensation of imminent cardiac arrest. 

A Toast to Celebrity Proposals

Smith & Sinclair initially began as a meet-cute event where adults could interact and possibly get their chance at love. 

At these events, our founders, Mel and Emile, put out their hand-crafted, alcohol-infused confectionaries as a treat for the daters to buy. In an ironic twist of fate, the gummies got a lot more action than any of the guests did, and thus, Smith & Sinclair were born. 

The point is that while you may never know what romantic gestures will help you seal the deal, you can always count on one thing, in and out of love: the thrilling, exotic taste creations known as Smith & Sinclair Cocktail Gummies bringing colour to your life.

You may not be able to afford celebrity proposals, but we can help you feel like one when you do decide to tie the knot. – visit our store to be at your boozy best when the time comes to say, “I DO!”

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Written by Adam Eli Bernhardt