From Poppy Delevigne to Jennifer Aniston: A Brief Guide to Notable Celebrity Proposals

Posted by , on October 9, 2012 at 4:15 pm

Most Stylish Proposal: Model (and our style crush) Poppy Delevingne announced her engagement to long-term boyfriend James Cook earlier today, and she broke the news via Twitter with a photo of a bespoke [...]

Most Stylish Proposal: Model (and our style crush) Poppy Delevingne announced her engagement to long-term boyfriend James Cook earlier today, and she broke the news via Twitter with a photo of a bespoke red jewelry box by Anya Hindmarch with the phrase “Will You Marry Me?” embossed on the lid. Delevingne tweeted her excitement writing "Errr YES... #happiestdayofmylife!" We couldn't be more excited by this news, and how utterly chic it is.

Most Classic Proposal: Actor Justin Theroux got the best birthday present of all when he proposed to his girlfriend Jennifer Aniston at his 41st birthday dinner at Blue Hill in the West Village two [...]

Most Classic Proposal: Actor Justin Theroux got the best birthday present of all when he proposed to his girlfriend Jennifer Aniston at his 41st birthday dinner at Blue Hill in the West Village two months ago — and she immediately accepted. Sure, the restaurant proposal may seem a little stale, but when you're Jennifer Aniston, it's all about keeping thing simple.

Most Extravagant Proposal: Singer-songwriter Seal held nothing back when proposing to his model girlfriend Heidi Klum in 2005. He flew Klum to the top of a 14,000-foot glacier where a specially made [...]

Most Extravagant Proposal: Singer-songwriter Seal held nothing back when proposing to his model girlfriend Heidi Klum in 2005. He flew Klum to the top of a 14,000-foot glacier where a specially made igloo, complete with a bed covered in rose petals, candles, food and champagne, was awaiting them. This proposal was definitely one for the books! 

Most Clichéd Proposal: Actor Tom Cruise popped the question to his girlfriend of only two months at the top of the Eiffel Tower in 2005. After actress Katie Holmes accepted, Cruise treated his [...]

Most Clichéd Proposal: Actor Tom Cruise popped the question to his girlfriend of only two months at the top of the Eiffel Tower in 2005. After actress Katie Holmes accepted, Cruise treated his bride-to-be to a candle-lit meal inside the tower at a high-profile restaurant called Le Jules Verne. Talk about tired, but everyone does go to Paris to fall in love. 

Best Reverse Proposal: When it came to getting hitched, singer Pink didn't wait around for her boyfriend Carey Hart to pop the question in 2005. Instead, she took matters into her own hands and proposed [...]

Best Reverse Proposal: When it came to getting hitched, singer Pink didn't wait around for her boyfriend Carey Hart to pop the question in 2005. Instead, she took matters into her own hands and proposed to him during one of his motocross races. We give Pink a lot of credit for being brave enough to ask her man for his hand in marriage rather than waiting for him to make a move.

A Proposal Fit for a Princess: Prince William decided to pop the question to his longtime girlfriend Kate Middleton while the two were vacationing in Kenya in 2010. The prince asked for Middleton's hand [...]

A Proposal Fit for a Princess: Prince William decided to pop the question to his longtime girlfriend Kate Middleton while the two were vacationing in Kenya in 2010. The prince asked for Middleton's hand in marriage while the two were lakeside on Africa's second-highest mountain, Mount Kenya. This royal and romantic proposal led to one of the most-talked about weddings of all time. 

Best Themed Proposal: Dean McDermott must have been in the holiday spirit when he proposed to actress Tori Spelling, his girlfriend of just three months, in 2006. McDermott took Spelling on a horse-drawn [...]

Best Themed Proposal: Dean McDermott must have been in the holiday spirit when he proposed to actress Tori Spelling, his girlfriend of just three months, in 2006. McDermott took Spelling on a horse-drawn carriage ride down a path illuminated by Christmas lights. The half-mile-long trail led to a table surrounded by Christmas trees where the actor presented his bride-to-be with a diamond and sapphire ring. We bet the couple had a very merry Christmas that year!

Most Dangerous Proposal: LL Cool J’s proposal to Simone Smith was anything but ordinary. The rapper popped the question to his soon-to-be fiance while driving and didn't even have a ring with him. Rather [...]

Most Dangerous Proposal: LL Cool J’s proposal to Simone Smith was anything but ordinary. The rapper popped the question to his soon-to-be fiance while driving and didn't even have a ring with him. Rather than the usual “Will you marry me?” he asked “Do you wanna do this?" He reportedly was driving his Porsche 110 mph and wouldn't slow down until Smith said yes. This sounds more like a hostage situation than a marriage proposal to us, but apparently it worked. They have been married since 1995! 

Least Impressive Proposal: NFL player Chad Ochocinco should consider himself lucky that “Basketball Wives” star Evelyn Lozada accepted his sub-par marriage proposal in 2011, which took place while the [...]

Least Impressive Proposal: NFL player Chad Ochocinco should consider himself lucky that “Basketball Wives” star Evelyn Lozada accepted his sub-par marriage proposal in 2011, which took place while the couple was playing Call of Duty. Apparently a jeweler came to the house, gave Lozada a ring, and then the pair continued on with their video game. We can’t imagine having to share this anticlimatic story with friends and family who inquire about the engagement expecting a romantic tale. Oh, and we all know how this marriage ended. 

Biggest Proposal Failure: It seems as if “Baywatch” star David Hasselhoff could benefit from a lesson or two in how to propose to someone. Apparently, the actor has asked his girlfriend Hayley Roberts to [...]

Biggest Proposal Failure: It seems as if “Baywatch” star David Hasselhoff could benefit from a lesson or two in how to propose to someone. Apparently, the actor has asked his girlfriend Hayley Roberts to marry him numerous times with no success. Considering one of these proposals took place in a dressing room last year, we can’t blame Roberts for turning Hasselhoff down.

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With today’s news that model and fashion It girl Poppy Delevigne got engaged (and let the world in on the adorable proposal via Twitter), we naturally had other high-profile proposals on the mind.

From Seal‘s over-the-top engagement to Heidi Klum — which took place in an igloo on top of a 14,000-foot glacier — to Tom Cruise asking for Katie Holmes‘ hand atop the Eiffel Tower, Hollywood has seen its fair share of enviable celebrity wedding proposals.

Click through the gallery above to see which star couples had the most noteworthy proposals!

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