18 Of The Most Surprising Celebrity Engagements Ever

When a couple dates for years, lives together and meets each other’s families, an engagement feels inevitable. In celebrity world, however, that is not necessarily the norm. Know someone a week and think they’re your soulmate? That kind of engagement is par for the course in Hollywood. Sometimes fans don’t even know two celebs are dating and — whoops! — now they’re married.

Over the years, there have been some bonkers celebrity engagements. Some have culminated in happy marriages — and then some haven’t even made it to the altar. Even so, here are some of the most shocking celebrity engagements… ever!

1. Khloe Kardashian and Lamar Odom

Talk about a whirlwind romance. These two not only shocked the world with their engagement a mere two weeks after they met, they then got married exactly a month after that initial meeting. I guess when you know you know? Except not so much for these two. After all kinds of drama — culminating in Lammy ODing in a brothel — these two are officially divorced. Lamar is currently trying to get his life back together, and Khloe is super happy with her new beau, basketball player Tristan Thompson.

2. Kendra Wilkinson and Hank Baskett

These two were engaged before anyone even knew that they were dating! Soon after Wilkinson moved out of the Playboy Mansion where she was one of Hugh Hefner‘s girlfriends, she found the man she wanted to spend the rest of her life with. Because I mean, c’mon, it wasn’t going to be Hef. Hef himself, though, was the one who broke the news about her engagement and confirmed that their wedding was taking place at the Playboy Mansion.

Kendra and Hank have had some major ups and downs over the years — including a cheating scandal and plenty of time on reality TV — but these two, and their two adorable children are still a happy family at the moment.

3. Mariah Carey and Nick Cannon

Carey and Cannon met, got engaged, and got married all within a six-week time span. It was truly shocking how quickly things moved with them, and even more shocking was the fact that these two were together at all. How did they even meet?! I mean, obviously if you’re a celebrity you can meet basically anyone but these two? Really?

By the time people could get used to them as a couple, the marriage was over. Though six years is a lot longer than most celebrity pairings, it still felt like it was cut off too soon. They currently co-parent their kids and seem to have a nice friendship after everything they’ve been through — so maybe it’s not so bad after all!

4. Perrie Edwards and Zayn Malik

This one wasn’t shocking because of who they were or how long they’d been together — the couple had been dating for years pre-engagement and considering he was a boy bander and she was a girl grouper, the pair seemed fairly well-matched. It was their ages that had everyone’s jaws dropping at the engagement news. At the time, the One Direction singer was 21 and his Little Mix bae was only 20! Sure, love can happen at any age, but in your early ’20s it’s hard to be certain of anything — let alone who you want to be with forever. Turns out they didn’t really know for sure because the engagement was called off. Pez claims to this day that Zayn broke off the engagement her via text. Yikes. At least we got “Shout Out to My Ex” out of the deal.

5. Blac Chyna and Rob Kardashian

It’s not the first and it’s definitely not the last Kardashian engagement to pop up on this list. This celebrity couple was a surprising one from the get-go. Chyna has a baby with Kylie Jenner‘s on-again-off-again flame, Tyga, so everyone was getting a bit too intertwined. The two were engaged a mere three months after they confirmed their relationship. One month later and Chyna’s pregnant! These two are full of shocking surprises.

They’ve had a lot of ups and downs in the last year and a half and these two are hella toxic. Thank god it seems their relationship is permanently dunzo as Chyna’s suing the Kardashian family.

6. Sofia Vergara and Joe Manganiello

This sexy pair got engaged only six months after getting together. When the two met she was actually engaged to another man. Clearly everything happens for a reason, though, because she broke off her engagement and got with Joe all in the same summer and now the two are as happy as can be. Sometimes things are just meant to be, and luckily this shocking celebrity engagement has a happy ending.

7. Winona Ryder and Johnny Depp

Ryder and Depp’s insane romance came as both their stars were rising in the ’90s. Depp was 27, Ryder was 18, and they were all about each other. Their highly publicized romance led to a highly publicized engagement five months after their first date. Johnny got his famous “Winona forever” tattoo afterward. Unlike that tat, these two were so not forever.

Their relationship was filled with drama and fights and they eventually went their separate ways. Johnny may have changed his tattoo to “Wino forever,” but we’ll always pine after the IT couple of the ’90s.

8. Gisele Bundchen and Tom Brady

The fact that these two got engaged and have been happily married since is a little shocking considering Gisele was Brady’s rebound from his ex, Bridget Moynahan. And did a mention the two began dating when Moynahan was three months pregnant with Brady’s child? A twisted web of ~drama~, to say the least.

These two pretty people have been making it work ever since, though, despite the rumors and insults hurled their way in the wake of their relationship becoming public. But I mean, look at them. What do they fight over, who’s prettier?!

9. Emma Roberts and Evan Peters

Which engagement do we think was the most shocking? Well, let’s see. The first one came months after Roberts was arrested for suspicion of domestic violence. The two seemed happy though, so alright, they’re engaged. And then they broke the engagement off. And then they got back together again. But then they broke up — again.
…And THEN it seems the engagement is back on?! Emma was seen with a giant rock on her finger earlier this year and the couple is definitely working it out. Not sure if we should be rooting for them or hoping they break up, but only time will tell what happens in this volatile romance.

10. Naya Rivera and Big Sean

After less than a year, Big Sean put a ring on it — a massive ring, at that. The Glee star and the rapper’s quick engagement may have been due to Naya’s reported jealousy issues. Turns out the jealousy issues weren’t necessarily uncalled for because rumors have it they called the engagement off because the rapper was making sweet *music* with someone else — Ariana Grande! The breakup was NOT amicable because Naya’s been spilling the tea ever since and Big Sean penned “I Don’t F*ck With You” about his ex.

11. Naya Rivera and Ryan Dorsey

Just three months after her split with Big Sean, the world was stunned again when Naya was suddenly married! A shocking engagement and a shocking marriage all rolled up into one. It was totally insane. Even in the celebrity world! And even crazier is the two got married on what was supposed to be Rivera and Big Sean’s wedding date. LOL.

Unfortunately, this relationship didn’t work out either, and Rivera confirmed last year that she and Dorsey are divorcing. Who knew rushing into marriage after three months may not be the best thing to do?!

12. Kim Kardashian and Kris Humphries

Six months into their relationship, Kardashian and Humphries were engaged — and with a ring the size of her fist. It was shocking that the goofy basketball star would want to get into that family. Though to be fair, the “Kardashian curse” started with him. No one was really convinced these two were ~meant to be~ which is probably why the marriage lasted a whole 72 days. Even Scott Disick knew it, as his horrified face at them kissing became a mega-viral GIF.

Let’s file this one under “reasons not to get married to someone with the same name as your mom.”

13. Ciara and Russell Wilson

On the heels of her split with rapper Future, Ciara got into a relationship with the football star, Russell Wilson. This duo got engaged after about a year of dating — and a year without sex, no less. It’s hard not to wonder if their quick engagement had a little something to do with the abstinence policy they were both practicing. Either way, the quick engagement, and nuptials have worked out well for the couple — they’re happy, in love, and have a daughter together. We ship it.

14. Courtney Stodden and Doug Hutchinson

This one was shocking, crazy, and all around weird. These two got engaged and then married when Stodden was 16 years old and Hutchinson was 51. Um… what? The world was shocked when the actor got engaged to the teenager and he was ousted from Hollywood. They’ve since split citing — surprise! — the age difference as the source of their issues. To be fair, though, their five-year marriage lasted longer than most celebrity pairings, so there’s that.

15. Miranda Kerr and Orlando Bloom

This one was surprising mostly because it was true. After three years of dating the couple had dodged engagement rumors left and right but denied them each time. And then, finally, it was for real! Sometimes it’s even more shocking when celebrities wait a normal amount of time to get to know someone before popping the question. These two got married a month later, but unfortunately, this marriage didn’t last and the two split.

16. Amal Alamuddin and George Clooney

After a little over six months of dating this power couple got engaged. The civil rights lawyer and famed Hollywood bachelor shocked the world with their low-key engagement mainly because Clooney had always been so adamant about never getting married. It seems he just hadn’t found anyone on his level, and Amal is way beyond his level so he definitely made a good call pinning her down. The two have twins and seem happy as ever!

17. Nikki Bella and John Cena

When Cena proposed to his wrestling girlfriend Nikki at WrestleMania the world was SHOCKED. Mainly because Cena had always vowed he’d never get married. He never hid that fact from his girlfriend, either, despite her hope that he would someday change his mind. So she was even more shocked than all of us were when he actually did change his mind and popped the question.

The wedding plans are underway and the couple knows one thing they both have no plans for — having kids. John is always there rooting for his lady on Dancing with the Stars — even people who never heard them are starting to fall in love with the couple!

18. Sophie Turner and Joe Jonas

The very latest in surprise celeb engagements is this Jonas Brother and the Game of Thrones star. The couple had barely confirmed their relationship and now they’re engaged!? They announced the happy news with dual Instagrams of the ring and simple “I said yes” and “She said yes” captions. Joe has been known for his player reputation in Hollywood, so he must really think Turner is the one to make her more than just another girlfriend. Also, she’s only 21. Best wishes to the newly engaged couple!

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