Top 10 Most Memorable Celebrity Engagements

Couple [Explored]_3719644439_lIf you’re planning a proposal or wedding, it’s only natural to borrow inspiration from the world’s most visible and glamorous examples. Hollywood’s ten most memorable betrothals didn’t all result in a wedding ceremony, but they certainly made tabloid splashes with their surprise announcements and gigantic diamonds. Take a trip through tabloid nostalgia with the following examples of memorable unions and pleasantly surprising promises.

10. Justin Theroux & Jennifer Aniston

For almost a decade, Jennifer Aniston was pigeon-holed as Miss Lonelyhearts by the Hollywood press machine. Being a childless divorcee certainly isn’t uncommon in Los Angeles, nor is it shameful in the slightest… but when Jennifer and her screenwriter-actor boyfriend announced their engagement, Jen’s fans breathed a collective sigh of relief. The whole country’s still rooting for their sweetheart to have a picture-perfect second wedding.

9. Kanye West & Kim Kardashian

Kanye has long declared himself a musical genius with no patience for gossip, so it was a bit out-of-character for him to choose a reality star to be his wife. But Kanye was true to form, shunning popular opinion to rent out a whole football arena in which to stage his proposal.

8. Brad Pitt and Angelina Jolie

After six children and eight years together, Hollywood’s golden couple finally announced their intentions to marry. Quintessential movie star Brad Pitt declared his reluctance to marry until same-sex couples were granted the same right, but by 2012, the couple’s children had convinced them to legalize their love anyway. They didn’t disclose the surprise ceremony until after it was over, making this one of the most secretive — yet highly publicized — engagements in Hollywood history.

7. Ryan Sweeting and Kaley Cuoco

The gossip world was still fixated on Kaley’s short showmance with Henry Caville when she stunned us all by announcing her quickie engagement on Twitter. The New Year’s Eve wedding was a surprise too, but nothing made Kaley’s fans happier than her shocking engagement announcement.

6. Benedict Cumberbatch & Sophie Hunter

The slim and sophisticated Brit earned the admiration (and obsession) of millions after his star turns in Sherlock and Star Trek. But after a few years of brief flings and budding super-stardom, Benedict did something supremely unexpected: he let his parents run a newspaper announcement to celebrate his engagement to a theater director and longtime friend. The world is still reeling from the loss of this particular bachelor, but Sophie and Benedict should be proud of how silent they managed to stay.

5. Nick Cannon & Mariah Carey

If 15 carats don’t get you a yes, there’s probably nothing on this planet that would! Nick Cannon set millions of tongues wagging when he popped the question to his longtime crush, and most predicted the short-lived union wouldn’t last much longer. The couple may be headed for divorce court now, but they did manage to eke out an elaborate wedding ceremony, several extravagant vow renewals and two beautiful children first.

4. Ellen DeGeneres and Portia de Rossi

The morning after the state of California approved same-sex marriage, daytime talk show host Ellen DeGeneres announced her own happy news to her studio audience. As Portia beamed in the audience of her partner’s syndicated national talk show, Ellen revealed to the world that the two could finally celebrate and legalize their love for one another.

3. Ben Affleck & Jennifer Lopez

Ben might have moved on to a different Jennifer (to the tune of four kids, at that), but the original Bennifer remains a pivotal and memorable moment in Hollywood engagements. Jennifer’s pink diamond is the royal standard for every celebrity engagement that has followed.

2. Prince William and Kate Middleton

After almost a decade of media speculation and off-and-on romance, commoner Kate Middleton was finally introduced as the future Queen of England. She even got to wear Princess Diana’s sapphire engagement ring for the royally sanctioned shots that introduced the couple to the world, making multiple generations jealous in one fell swoop.

1. George Clooney and Amal Alamuddin

From bets with co-stars to magazine covers, George Clooney was never shy about his self-imposed ban on marriage. So when Hollywood’s most notorious bachelor announced that new girlfriend and esteemed barrister Amal Alamuddin would be his wife, it was an understandable shock to the public and the press alike. The only thing that matched the engagement’s wow factor was the wedding itself, which dominated Venice for a whole long weekend.

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