Celebrities engaged more than once – See all their rings

We’ll admit it: When a celebrity gets engaged, we immediately want to see the bling. And since this is Hollywood, where stars tend to get serious fast and marry multiple times, many have had the pleasure of wearing more than one beautiful engagement ring. Join Wonderwall.com as we take a look at all the rings from all the times your favorite singers and actresses were engaged, starting with Ariana Grande, who announced her engagement to real estate agent Dalton Gomez on Dec. 20, 2020, and was previously engaged to comedian Pete Davidson in 2018…

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Pete Davidson’s ring

“Saturday Night Live” star Pete Davidson proposed to Ariana Grande after barely a month of dating in 2018. He commissioned New York City-based jeweler Greg Yuna, who goes by the name Mr. Flawless, to create a custom ring featuring a $93,000 VVS1 clarity pear-shaped diamond set in platinum surrounded by smaller diamonds. The pair split after six months together.

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Dalton Gomez’s ring

In December 2020, Ariana Grande took to Instagram to reveal that her love of nearly a year, real estate agent Dalton Gomez, had proposed. “forever n then some,” she captioned a slideshow of photos with her fiancé that included this close-up pic of her stunning and unique diamond-and-pearl engagement ring.

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Gwen Stefani split from first husband Gavin Rossdale in 2015 after nearly 13 years of marriage and two decades as a couple. In October 2020, the No Doubt frontwoman accepted a marriage proposal — and an incredible diamond ring — from her “The Voice” co-star Blake Shelton. Keep reading to see Gwen’s very different rings…

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Gavin Rossdale’s rings

Bush frontman Gavin Rossdale proposed to Gwen Stefani in early 2002 and they wed that September. During their engagement, Gwen sported a unique ring — a thick, wide metal band set with a row of diamonds in the middle that she wore bookended by two thin diamond bands (inset). Not long after saying “I do,” Gwen swapped it for a heart-shaped diamond ring that she wore until she and Gavin split in 2015.

Blake Shelton’s ring

After more than five years of dating, Gwen Stefani accepted a marriage proposal from country music star Blake Shelton — who presented her with a whopper of a ring featuring a square or emerald-cut center diamond flanked by two baguette diamonds — on his Oklahoma ranch in October 2020.

Scarlett Johansson has been married three times and divorced twice. She wed Ryan Reynolds in 2008 and Romain Dauriac in 2014. In 2019, she accepted a marriage proposal from “Saturday Night Live” writer-star Colin Jost and they tied the knot in October 2020. Keep reading to see ScarJo’s three very different engagement rings…

Ryan Reynolds’ ring

Ryan Reynolds proposed to Scarlett Johansson in early 2008 with a traditional round-cut diamond set on a yellow gold band. They married that September but split two years later.

Romain Dauriac’s ring

French journalist-turned-businessman Romain Dauriac proposed to Scarlett Johansson in the summer of 2013 with a vintage sparkler featuring three round diamonds in an Art Deco setting filled with smaller diamonds. The pair, who have a daughter, Rose, married in 2014 and split two years later.

Colin Jost’s ring

“Saturday Night Live” writer and “Weekend Update” anchor Colin Jost proposed to Scarlett Johansson in May 2019 after two years of dating. A few months later, the “Avengers” franchise star publicly debuted her engagement ring at the Marvel Studios Panel during Comic-Con International in San Diego in July 2019. A jewelry expert told Page Six that the stunner appears to be an 11-carat light-brown diamond that’s a mix between a pear and oval shape set on an unexpected dark band. Jewelry website The Adventurine reported that the ring appears to be a design from Taffin’s James de Givenchy (the nephew of famed designer Hubert de Givenchy).

Jennifer Lopez has been married three times and also enjoyed a high-profile engagement to Ben Affleck during their “Bennifer” period in the early aughts. In March 2019, she said “yes” when Alex Rodriguez popped the question. Keep reading to see the classic and colorful engagement bling she got from her four big exes and her latest fiancé…

Ojani Noa’s ring

Jennifer Lopez wed waiter Ojani Noa in 1997, but their marriage only lasted until the following year. She sported a simple diamond engagement ring and a gold wedding band during their short-lived union.

Cris Judd’s ring

After ending a long relationship with Sean “Diddy” Combs, Jennifer Lopez quickly moved on with dancer Cris Judd and after just a few months of dating, they got engaged. J.Lo wore this emerald-cut diamond ring in the months leading up to their September 2001 wedding. She and Cris split less than a year after saying “I do.”

Ben Affleck’s ring

In 2002, Ben Affleck proposed to “Gigli” co-star Jennifer Lopez with a 6.1-carat rare pink diamond ring flanked by smaller white diamonds. The Harry Winston sparkler was estimated to be worth $2.5 million at the time. They called off their 2003 wedding just days before they were set to walk down the aisle, and a few months later, in early 2004, confirmed that they’d broken up for good.

Marc Anthony’s ring

Just months after Bennifer’s demise, Jennifer Lopez married salsa singer Marc Anthony in June 2004. He reportedly proposed with a rare blue 8.5-carat diamond engagement ring flanked by smaller white diamonds, which was estimated to be worth $4 million. They split in 2011.

On March 9, 2019, Jennifer Lopez posted this Instagram photo revealing her engagement ring from Alex Rodriguez. They’d been dating for just over two years when the retired baseball legend proposed with this stunning emerald-cut diamond while he and Jennifer were on a beach vacation.

Jennifer Aniston’s first marriage, to Brad Pitt, lasted four and a half years. Her second marriage, to Justin Theroux, lasted two and a half years. Keep reading to see her very different diamond engagement rings from both men.

Brad Pitt’s ring

Brad Pitt worked with jeweler Silvia Grassi Damiani and her Italian company, Damiani International, to design a unique engagement ring for Jennifer Aniston in 1999 featuring a raised galaxy-style swirl of diamonds. The couple later sued the jeweler, who also designed the wedding bands they exchanged at their 2000 nuptials, for $50 million after, they alleged, her company started producing copies of Jen’s ring and selling them. They later settled out of court.

Justin Theroux’s ring

Justin Theroux surprised Jennifer Aniston with a wedding proposal on his 41st birthday in August 2012 and presented her with a huge 8-carat diamond ring. “It’s a rock, I know,” she later told The New York Times. “He rocked it up. It took me a while to get used to it.” Though she loved it, she also admitted, “I’m not a diamond girl. I’m more Indian jewelry and stuff.” The couple, who married in August 2015, announced in February 2018 that they’d split.

Pop star Katy Perry has sported two engagement rings from two very famous men…

Russell Brand’s ring

Katy Perry got engaged to Russell Brand in India in late 2009 after four months of dating. The British comedian and author turned to New Delhi-based jewelry designer Hanut Singh, who crafted a ring of yellow gold that reportedly featured a 3-carat Golconda diamond, “the most magical of Indian diamonds from many hundred years ago when the Golconda mines were flourishing,” the designer told Radar Online. The couple married in India 10 months later in October 2010. But 14 months after that, Russell ended their marriage via text.

Orlando Bloom’s ring

Katy Perry accepted a marriage proposal from Orlando Bloom on Feb. 14, 2019, after three years of on-off dating. The couple revealed her unique flower-shaped engagement ring in dual Instagram posts the following day, with the pop star captioning hers “full bloom” and the “Lord of the Rings” actor captioning his “Lifetimes.” Within hours of the news going public, jewelry experts weighed in on the value of the beautiful bauble, which features a dark pink center stone and eight petal-like diamonds set in yellow gold surrounding it. If the stone is a ruby, the value of the ring would be in the $300,000 to $500,000 range, a jewelry expert told Us Weekly. However, if the stone is a pink diamond, it could be worth $5-6 million.

Model Miranda Kerr’s marriage to Orlando Bloom ended in 2013. She wed Snapchat CEO Evan Spiegel in 2017. See both of her engagement rings next…

Orlando Bloom’s ring

During her three-year marriage to Orlando Bloom, Miranda Kerr wore a vintage-style engagement ring in a floral-inspired design featuring an oval-shaped center diamond surrounded by smaller round diamonds, all set in yellow gold.

Evan Spiegel’s ring

Snapchat co-founder Evan Spiegel proposed to Australian model Miranda Kerr in 2016 with a classic round-cut diamond flanked by tapered baguettes. (See the close-up photo she shared on social media here.) The couple married in 2017.

Lady Gaga and actor Taylor Kinney called off their engagement in 2016 after nearly five years together. In late 2018, she confirmed reports that she was engaged to her agent, Christian Carino, but that one wouldn’t last either. See her very different rings next…

Taylor Kinney’s ring

“Chicago Fire” actor Taylor Kinney popped the question to Lady Gaga with a heart-shaped diamond ring on Valentine’s Day 2015. Jeweler Lorraine Schwartz described it to E! News as “the most beautiful” and “high quality” diamond. While she didn’t reveal its size or cost, jewelry experts estimated the ring, which featured a stone in excess of 6 carats, was worth around $500,000. But by July 2016, the couple had split.

Christian Carino’s ring

In February 2017, Lady Gaga went public with a new romance at the Super Bowl: She’d started seeing her agent, Christian Carino. Reports claimed the pair quietly got engaged during the summer of 2017, but Gaga didn’t publicly confirm that Christian was her fiancée until October 2018. It was a poorly kept secret however, as she’d been sporting an enormous pink gemstone ring surrounded by diamonds for nearly a year at that point. In February 2019, People magazine confirmed speculation that Gaga and Christian had quietly split after the music star attended the Grammys minus her ring and her man.

Gwyneth Paltrow has accepted marriage proposals from Brad Pitt, Chris Martin and Brad Falchuk, though she only walked down the aisle twice. See how her three engagement rings compare…

Brad Pitt’s ring

Gwyneth Paltrow and Brad Pitt started dating in 1994 after meeting on the set of “Seven.” After Brad proposed in 1996, Gwyneth was seen wearing this diamond solitaire engagement ring. But the beautiful blonde couple never made it down the aisle: They split up in 1997.

Chris Martin’s ring

In 2003, Coldplay singer Chris Martin gave Gwyneth Paltrow a ring featuring an Asscher-cut diamond (estimated at 8 carats!) surrounded by micropave diamonds set on a band embedded with more micropave diamonds. The couple eloped in December that year and announced their “conscious uncoupling” a decade later in March 2014.

Brad Falchuk’s ring

After months of speculation, in January 2018, Gwyneth Paltrow and writer-producer Brad Falchuk finally announced that they were engaged. The same month, she publicly debuted her non-traditional engagement ring, which appears to be a large, organically cut dark blue sapphire set in a cradle of white gold or platinum on a band studded with diamonds. They married at her New York home in the Hamptons on Sept. 29, 2018.

“The Big Bang Theory” star Kaley Cuoco has been married twice and was engaged once before she was ever a Mrs. See her engagement rings from addiction specialist and former Danzig bassist Josh “Lazie” Resnik, tennis pro Ryan Sweeting and equestrian Karl Cook next…

Josh “Lazie” Resnik’s ring

Kaley Cuoco accepted a marriage proposal from addiction specialist Josh “Lazie” Resnik, a former bassist for Danzig, in October 2011. But by the following March, it was over. For a few months, the “The Big Bang Theory” actress sported Josh’s ring, which featured a central diamond in a tall halo setting.

Ryan Sweeting’s ring

Ryan Sweeting proposed to Kaley Cuoco in September 2013 after just three months of dating. Her $65,000 ring from Red C Jewels featured a 2.5-carat cushion-cut diamond in a halo setting on a pave diamond band. The couple wed on New Year’s Eve the same year but split less than two years later.

Karl Cook’s ring

When professional equestrian Karl Cook proposed to Kaley Cuoco on Nov. 30, 2017 — her 32nd birthday — the actress cried tears of joy and shared a close-up of her ring on her Instagram Story. Karl surprised her with some stunning bling — a pear-shaped diamond set on a thin band of smaller stones from Nadis Diamonds (he later posted a photo of the ring in its box on Instagram). The couple married on June 30, 2018, at Karl’s Southern California horse ranch.

The three engagement rings that Heidi Klum has worn over the last three decades during her romances with Ric Pipino, Seal and Tom Kaulitz are incredibly different. See them all next…

Ric Pipino’s ring

German model-turned-mogul Heidi Klum wore a modest yellow gold and diamond ring that also featured a few emerald-green stones during her marriage to her first husband, hairstylist Ric Pipino. The couple wed in 1997 and divorced in 2002.

Seal’s ring

Music star Seal proposed to Heidi Klum in December 2004 on a glacier in Whistler, British Columbia, Canada, and the couple married in May 2005 on a Mexican beach. Heidi’s engagement ring from the “Kiss From a Rose” singer featured an enormous oval yellow diamond (estimated at between 8 and 10 carats!) set in complementary yellow gold. The couple divorced in 2012.

Tom Kaulitz’s ring

On Christmas Eve morning in 2018, “Project Runway” host Heidi Klum accepted a marriage proposal from German rocker Tom Kaulitz after less than a year of dating. The Tokio Hotel guitarist “drew the dream ring for Heidi and then went in search of the right stones. He didn’t just go to the store,” a friend of Heidi’s told People magazine of the model’s unique blue-green-hued engagement bauble. “He knew Heidi’s favorite color was green, so he searched for the perfect green stone, an alexandrite, and then found the perfect diamonds to accentuate it.” The couple quietly married in February 2019.

Mariah Carey’s engagement ring mantra might as well be “go big or go home!” See the elusive chanteuse’s rings from her two husbands and billionaire ex-fiancé next…

Tommy Mottola’s ring

Mariah Carey wore a large square-cut diamond ring flanked by two smaller side stones when she became Mrs. Tommy Mottola in 1993. The singer split from the Sony Music head in 1997.

Nick Cannon’s ring

Nick Cannon proposed to Mariah Carey in 2008 with a jaw-dropping 17-carat diamond ring from Jacob & Co. reportedly worth $2.5 million. The bling featured a 10-carat emerald-cut fancy light pink center stone surrounded by 58 intense pink diamonds flanked by two more diamonds.

James Packer’s ring

Australian billionaire James Packer proposed to Mariah Carey in January 2016 with a 35-carat Wilfredo Rosado-designed ring reportedly worth $7.5 to $10 million. “I took the standards super-high, and I wanted to create a ring that could not be measured up to,” the designer told Vogue, adding that “it was about mixing simplicity with volume, which is very difficult to do.” But just 10 months later, the engagement was over. According to People magazine, Mariah got to keep the ring thanks to the terms of a split settlement. In May 2018, Page Six reported that the diva had quietly sold the ring to a Los Angeles jeweler for $2.1 million.

There aren’t any photos of Sofia Vergara’s ring from first husband Joe Gonzalez, the high school sweetheart she married back in her native Colombia when she was just 18, but wait till you see her bling from ex-fiancé Nick Loeb and current husband Joe Manganiello!

Nick Loeb’s ring

Businessman Nick Loeb proposed to Sofia Vergara in 2012 after about four years of dating with a ring from Long Island’s London Jewelers. It featured a 7-carat cushion-cut diamond center stone flanked by two smaller diamonds. “It is perfection. If it was bigger, it would be too big to wear,” Sofia told Lucky of her bling. “But if it was smaller, I would not like.” She and Nick split less than two years later.

Joe Manganiello’s ring

After just a few months of dating, Joe Manganiello proposed to Sofia Vergara over the Christmas holidays in 2004 with a gorgeous diamond ring believed to weigh 7 carats. “You know with me it’s all about the bling bling so he knew what I needed,” the “Modern Family” star joked to “Access Hollywood” a month after Joe’s proposal. “I opened it up and I checked it to see. And then I was like, ‘Yes!’ No, I’m joking, he’s so handsome that I would have said ‘OK’ anyway.” The couple tied the knot in November 2015.

Reese Witherspoon’s been married twice: first to actor Ryan Phillippe, then to talent agent Jim Toth. Keep reading to see how her engagement rings from the men compare…

Ryan Phillippe’s ring

Ryan Phillippe gave “Cruel Intentions” co-star Reese Witherspoon, whom he wed in 1999, a stunning vintage-inspired engagement ring. It was reportedly from jeweler Neil Lane and featured a 4.5-carat Asscher-cut diamond in an Edwardian-style setting. The couple split in 2006.

Jim Toth’s ring

CAA agent Jim Toth proposed to Reese Witherspoon in 2010 with a 4-carat Ashoka diamond set on a pave diamond-and-platinum band. They married in 2011.

Kim Kardashian West has been married three times. Though we couldn’t find a photo of her ring from her first husband, music producer Damon Thomas — they were married from 2000 to 2004, before she was famous — we bet your jaw will drop when you get a close-up look at her ginormous rings from her second and third husbands…

Kris Humphries’ ring

NBA player Kris Humphries proposed to Kim Kardashian West in 2011 with a Lorraine Schwartz ring featuring a 16.21-carat emerald-cut center diamond flanked by two 1.8-carat diamonds. Her matching wedding band featuring more emerald-cut diamonds reportedly weighed about 15 carats. Kim famously left Kris just 72 days after their August 2011 wedding, and in 2013, he sold her engagement ring in a Christie’s auction for $749,000.

Kanye West’s ring

Rapper and fashion designer Kanye West proposed to Kim Kardashian West on her 33rd birthday in October 2013 with another whopper of a ring featuring a 15-carat colorless, flawless, cushion-cut diamond from jeweler Lorraine Schwartz. They married in Italy the following May.

Jessica Simpson has been married twice: She and Nick Lachey walked down the aisle in 2002 and she and Eric Johnson said “I do” in 2014. See the rings both guys gave her next…

Nick Lachey’s ring

Pop stars Nick Lachey and Jessica Simpson got engaged aboard a yacht in Hawaii just before Valentine’s Day in 2002. The 98 Degrees singer slipped this engagement ring, which features a 4-carat pear-shaped diamond center stone, on her finger that day and later added a blinged-out diamond wedding band. Their marriage ended in 2005.

Eric Johnson’s ring

When former NFL player Eric Johnson proposed to Jessica Simpson with Led Zeppelin’s “Since I’ve Been Loving You” playing on Nov. 11 at 11:11 a.m., he gave her a non-traditional sparkler from jeweler Neil Lane’s collection of vintage pieces — a 1910 Tiffany & Co. ring featuring a 5-carat ruby (her birthstone) flanked by two pear-shaped diamonds. When it came time to choose a wedding band, Neil created something he knew Jessica would love. “She’s a Texas girl so we didn’t do a little band. She wanted her bling!” he explained of the singer-designer’s yellow and rose gold band set with 5 carats of marquise and round diamonds.

Jessica Simpson’s little sister, Ashlee Simpson, also has a ruby engagement ring. Keep reading to see if it was first husband Pete Wentz or second husband Evan Ross who gave it to her…

Pete Wentz’s ring

Pete Wentz proposed to Ashlee Simpson in 2008 with a ring featuring a 4-carat Asscher-cut diamond surrounded by a pave-diamond halo. They ended their marriage in 2011.

Evan Ross’s ring

Before his January 2014 proposal, Evan Ross worked with Neil Lane to come up with a unique ruby-and-diamond engagement ring for Ashlee Simpson. He chose a piece from the jeweler’s vintage archival collection featuring a marquise-cut diamond surrounded by small rubies in an elongated navette style — and then asked Neil to tweak it and add a diamond sleeve. The end result? A 5-carat ring crafted from 14 rubies and 140 white diamonds all set in platinum and gold. Ashlee wed Evan in August 2014.

Kate Hudson has sported two engagement rings over the years, both from rock stars: Black Crowes frontman (and ex-husband) Chris Robinson and Muse frontman (and ex-fiancé) Matt Bellamy. Engagement buzz has surrounded Kate and former Chief frontman Danny Fujikawa — the father of her third child, daughter Rani — but the couple has yet to confirm plans to wed. Now see Kate’s rings…

Chris Robinson’s ring

When they got engaged, Black Crowes frontman Chris Robinson gave Kate Hudson a Neil Lane ring featuring a 5-carat Asscher-cut diamond in an Art Deco-style setting. The couple wed on New Year’s Eve in 2000 and split in 2006.

Matt Bellamy’s ring

British rocker Matt Bellamy proposed to Kate Hudson in 2011 with an enormous emerald-cut diamond ring — experts estimated it at 9 carats with a value of $200,000 — flanked by two diamond baguettes. The couple split in 2014 before they ever walked down the aisle.

Socialite-turned-reality star (and now DJ) Paris Hilton has a long and storied love life that spans two decades, during which she’s been engaged three times. Model Jason Shaw was her first fiancé, followed by Greek shipping heir Paris Latsis and “The Leftovers” actor Chris Zylka. See her memorable rings next…

Fiancé No. 1

Paris Hilton was just 21 when she and model Jason Shaw got engaged. Their betrothal lasted from 2002 to 2003, but no photos of her ring seem to exist.

Paris Latsis’s ring

Paris Hilton started seeing Paris Latsis in late 2004 and by the following May, they were engaged. The Greek shipping heir gave the reality TV star a jaw-dropping 24-carat diamond ring, which he had to replace for a reason that is so very Paris. “[She] started complaining how heavy her 24-carat ring was and that her finger hurt,” a source told Us Weekly at the time, so her fiancé “got her a more manageable diamond-less platinum Cartier band for everyday wear.” The couple ended their engagement in November 2005.

Chris Zylka’s ring

Actor Chris Zylka of “The Leftovers” fame proposed to Paris Hilton in Aspen, Colorado, over the 2017 holidays with a ginormous 20-carat pear-shaped diamond ring from Greene & Co. worth $2 million. He chose that cut, jeweler Michael Greene told The Knot, because Paris has long admired her mother’s ring, which also features a pear-shaped diamond. The bling was so valuable, Paris hired security to accompany her when she wore it. After she and Chris split in November 2018, she said she planned to keep the ring.

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