Celebs Who Got Engaged More Than Once: A Look at All Their Rings


Most of us like to imagine that our “happily ever after” will only come once. You meet the love of your life, you get engaged, and then enjoy happiness forever… right?

In reality, plenty of people get engaged more than once before they find “Mr. Right.” It even happens to the hottest celebrities in the world. This may lead to baggage, but it also leads to some jaw-dropping engagement rings.

We’ve got the full story on your favorite celebs and the amazing engagement rings they have collected over the years!

Scarlett Johansson

Scarlett Johansson has always been a popular and gifted actor, but starring as Black Widow in the Marvel Cinematic Universe propelled her into superstardom. Interestingly, Johansson’s private life has had much more dramatic romantic entanglements than her onscreen persona ever had.

In 2008, she got engaged to future Deadpool star Ryan Reynolds. They kept things simple with a round-cut diamond set tastefully on a yellow gold band. Sadly, this couple split up in 2011 after nearly three years of marriage.

In 2013, ScarJo got engaged to French journalist and business mogul Romain Dauriac. And he channeled the beauty of France with an Art Deco ring filled with smaller diamonds and topped with three immaculate round diamonds. They got married and even had a daughter (Rose) in 2014, but split up in 2017.

Most recently, Johansson got engaged to Saturday Night Live writer and actor Colin Jost in 2019. She debuted her engagement ring at Comic-Con International, showing the world a dark band topped with an pear-shaped 11-carat diamond in a champagne color. The ring’s estimated value is between $350,000 and $400,000. She and Jost got married in October 2020.

Jennifer Aniston

Back when Friends became a hit show, Jennifer Aniston cemented herself as one of the most beautiful women on the planet (with a hairstyle to die for, no less). Is it any wonder that she ended up marrying two of the most beautiful men on the planet?

In 1999, she famously got engaged to Brad Pitt. The movie star gave her a ring with a round brilliant diamond surrounded by a swirl of diamonds in the shape of the Milky Way galaxy. Pitt helped design the ring, which he wanted to symbolize “eternity.” The ring is estimated to be worth $500,000. Unfortunately, the pair split in 2005.

Then, Aniston got engaged to Justin Theroux in 2012. He gave her an intimidating 8-carat diamond ring, also estimated at $500,000. They enjoyed a happy marriage before splitting up in 2018.

Gwyneth Paltrow

Gwyneth Paltrow alternates between acting and running her lifestyle brand Goop. Along the way, though, she has been engaged several times.

Back in 1996, she got engaged to Hollywood hunk Brad Pitt. He gave her a lovely diamond solitaire engagement ring, but the two split before they could ever get married.

In 2003, she got engaged to Coldplay singer Chris Martin. He gave her a ring with a micropave diamond band, micropave diamond setting, and an eight-carat Asscher-cut diamond. Those two split in 2014, which is when Paltrow coined the “conscious uncoupling” phrase.

In 2018, Paltrow got engaged to writer and producer Brad Falchuk. In a twist, this latest ring is an organically cut blue sapphire on a diamond-covered band, a nontraditional ring for a very nontraditional girl. They got married later that year.

Katy Perry

Katy Perry is living proof that the heart wants what the heart wants. After all, this superstar singer has married two very different men over the course of her career.

First, she got engaged to provocative comedian and actor Russell Brand in 2009. He gave her a yellow gold ring with a 3-carat Golconda diamond, estimated at $120,000. They had a magical wedding in India in 2010. Unfortunately, they divorced two years later.

But in 2019, Perry got engaged to a man who was a “teenage dream” to fans all around the world: actor Orlando Bloom! He gave her a ring with eight diamonds arranged like flower petals around a yellow gold band. And the ring features a large pink stone that may either be a dazzling ruby or a dazzlingly-expensive pink diamond. In the latter case, the ring is estimated to be worth $5 million!

Reese Witherspoon

Reese Witherspoon has built an entire career out of being the adorable girl next door. But even America’s girl next door needed a couple of tries to get her love life in order. 

First, she married fellow actor Ryan Phillippe in 1999. He proposed with a classy Neil Lane ring in an Edwardian setting featuring a 4.5-carat Asscher-cut diamond. Unfortunately, they split in 2006.

In 2010, Witherspoon got engaged to Creative Artist Agency rep Jim Toth. He gave her a pave diamond-and-platinum band featuring a stunning 4-carat Ashoka diamond, estimated at over $150,000.

Kaley Cuoco

On The Big Bang Theory, we watched Kaley Cuoco’s character Penny struggle to find love before finally settling down with Leonard. And it turns out this was a pretty good reflection of Cuoco’s own love life off the screen.

Back in 2011, she got engaged to former Danzig bassist Josh “Lazie” Resnik. The ring had a central diamond and a tall halo setting, but they were only engaged for a few months before breaking things off and never getting married.

In 2013, Cuoco got engaged to Ryan Sweeting after only dating a few months. He gave her a gorgeous ring with a pave diamond band, a halo setting, and a tasteful 2.5 carat diamond. They ended up getting married on New Year’s Eve but splitting less than two years later.

And in 2017, Cuoco got engaged to pro equestrian Karl Cook. The ring he gave her featured a pear-shaped diamond that was set on a relatively thin band. The band was made of a series of smaller stones from Nadis Diamonds. They got married in 2018.

Leave a Reply

Your email address will not be published.