The fastest engagements in Hollywood history - including a 55-hour marriage


The love lives of Tinsel Town's residents are nothing if not dramatic, from Britney Spears' 55-hour marriages to Tommy Lee's popping of the question after just four days


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Hollywood's romantic curse has wiped out even the most beloved of couples; however, as much as the world of showbiz can tarnish a relationship, the mesmerising magic of the movies can cause famous stars to trip and fall in love with one another faster than they learn their partner's full name.

From 55-hour marriages to engagements following four-day-long relationships, A-lister life can be an intoxicating recipe for dizzying whirlwind love stories. 

But as quickly as they are sparked, many fast flames die out, sometimes within a matter of hours if your name is Britney Spears and Jason Alexander. Let's take a look at some of the entertainment industry's speediest engagements to date…

Pamela Anderson and Tommy Lee© WireImage

Pamela Anderson and Tommy Lee

Playboy model and Baywatch star Pamela Anderson dived headfirst into her relationship with rocker Tommy Lee, agreeing to marry him a mere 96 hours after their initial meeting.

The infamous couple walked down the aisle four days after meeting in 1995, on a beach in Cancun. Their romance was tumultuous and was on-and-off-again from the moment it started. 

In the years that followed their quick engagement and wedding, Pamela welcomed two sons with the Mötley Crüe drummer: Brandon Thomas Lee on 5 June 1996 and Dylan Jagger Lee on 29 December 1997. 

They split for good in 1998 after the model filed for divorce following Tommy's arrest for spousal battery.

Ariana Grande and Pete Davidson © WireImage

Ariana Grande and Pete Davidson

Singer and Wicked star Ariana Grande and SNL comedian Pete Davidson revealed they were engaged to be married weeks after they started dating in June 2018. 

The pair appeared on the late-night sketch show together but were in relationships at the time and only reconnected when Ariana returned to New York to work on her album. 

She told Jimmy Fallon during an appearance on The Tonight Show: "We never exchanged numbers or anything, we weren't even friends for the longest time, but I had the biggest crush in the whole world on him the whole time - like forever. Like, my friends used to make fun of me for it." 

Pete opened up about their engagement and told GQ at the time: "The day I met her, I was like, 'Hey, I'll marry you tomorrow'. She was calling my bluff. I sent her a picture [of engagement rings]. I was like, 'Do you like any of these?' She was like, 'Those are my favorite ones,' and I was like, 'Sick.'"

The couple broke up months later in October 2018, without ever making it down the aisle.

Britney Spears and Jason Alexander© PA Images via Getty Images

Britney Spears and Jason Alexander

During her heyday, singer Britney Spears decided she was in the mood to tie the knot with her childhood friend, Jason Alexander, in 2004. 

The lovesick pair headed to Las Vegas and got married, only for it to be annulled 55 hours later. At the time, Britney claimed she was "very drunk" and "lacked understanding of her actions". 

Years later, during her wedding to her ex-husband Sam Asghari, he was convicted of trespassing and battery after he broke into her home and attempted to live-stream the ceremony.

Mariah Carey and Nick Cannon© Getty Images

Mariah Carey and Nick Cannon

Hit maker Mariah Carey and television host Nick Cannon dominated headlines for their speedy engagement after just six weeks of dating back in 2008. 

They shocked the press when they wed in a surprise ceremony and welcomed twins, Monroe and Moroccan, who were born in April 2011. 

Three years later, in 2014, they filed for divorce and their arrangement was finalised in 2016.


Khloe Kardashian and Lamar Odom © NBCU Photo Bank via Getty Images

Khloe Kardashian and Lamar Odom

The youngest of the original Kardashian sisters, Khloe and her basketballer ex-husband Lamar Odom got engaged and married one month after meeting each other at a party for NBA player Ron Artest in Los Angeles. 

Just a few weeks after their first meeting, Lamar popped the question in September 2009, and what followed was a lavish celebrity wedding that was filmed for Khloe's reality show, Keeping Up With The Kardashians.

After years of ups and downs, including substance abuse and infidelity, the couple finalised their divorce in 2016.

George Clooney and Amal Alamuddin© GC Images

George Clooney and Amal Alamuddin

A-lister and notorious bachelor George Clooney wasted no time when he met his now-wife, human rights barrister Amal Alamuddin, in July 2023. 

The pair met through mutual friends when Amal unexpectedly showed up at his Italian villa in Lake Como and were engaged to be married just seven months later. 

They tied the knot in a stunning Venice ceremony exactly five months after the star popped the question and welcomed twins, Ella and Alexander, two years later. 

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