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Celebrities who’ve been engaged more than once

While some couples are lucky enough to last a life time, most of us have to kiss a few frogs before we find our perfect match. The same goes for celebrities, too.

Whilst putting a ring on it marks the start of a happily ever after for some people, that’s not always the case – especially in Hollywood.

Engagement ring specialists at Steven Stone have taken a look into some of the celebrities who’ve been engaged multiple times and revealed everything you need to know about their engagement rings…

Instagram: @ladygaga
Instagram: @avrillavigne
Instagram: @kimkardashian

Jennifer Lopez

Having been engaged six times, JLo is the Queen of engagements.

In 1997, Jen was fresh on the block when she married restauranteur Ojani Noa, who swept her off her feet with her very first engagement ring. When he popped the question, he presented her with a pear-shaped diamond ring on a yellow gold band – thought to be worth a £100,000.

Chris Judd and Jennifer Lopez first crossed paths in 2000, on the set of the ‘Love Don’t Cost a Thing’ music video, where Cris was a backup dancer for J-Lo. That same year, in June, he reportedly proposed at a barbecue, before the couple wed in a secret ceremony in September, where 170 guests attended. While the wedding may have been low-key, her engagement ring certainly wasn’t – our experts valued her incredibly emerald-cut diamond ring to be worth around £200,000.

When Ben Affleck and J-Lo announced their first relationship way back in in 2002, the world followed their every move, in awe of the A-list couple. And, they didn’t leave fans waiting for long as they got engaged that same year. The engagement ring was a massive 6.10 carat radiant cut, designed by celebrity jeweller Harry Winston, which reportedly cost Ben Affleck a whopping £855,000 ($1.2 million) at the time. However, now, as pink diamonds have soared in value, J-Lo’s ring is worth a lot more than it was back then. Our diamond experts estimate it to be worth over double the price now, valuing the ring at £2,000,000.

After splitting from Ben Affleck, J-Lo dated pop sensation, Marc Anthony, and yet again we saw another huge rock be unveiled. Weighing in at a huge 8.5 carats, the sparkler featured a rare blue diamond is worth over £3,000,000.

Just when we thought J-Lo’s engagement ring couldn’t get any bigger, Alex Rodriguez proved us wrong. For his romantic beach proposal in March 2019, A-Rod unveiled a very classic emerald-cut diamond with simple but elegant solitaire mounting. The diamond looks to be around 15 carats and is completely colourless with the highest clarity. Our experts valued the sparkler at £1,500,000.

When J-Lo announced her second engagement to Ben Affleck, we were keen to get the first look. The images revealed a show stopping green diamond ring, which is unlike anything we’ve seen before. Just like the pink diamond engagement ring she received from Ben Affleck previously, the ring is worth millions. The centre stone is an estimated 9 to 10 carats, with an elongated cushion cut. It also looks to feature two tapered baguettes, making this a three stone ring. Our experts valued it at over £2,800,000 ($3,000,000).

Eva Longoria

Tony Parker proposed to Eva Longoria with a four-carat emerald cut ring with emerald side stones. Worth £120,000 ($150,000), the stunning ring was designed by Jean Dousset.

Eva Longoria’s bling from her husband José Antonio Baston – who proposed during the couples holiday in Dubai – boasts a large ruby centre stone. Often compared to Kate Middleton’s engagement ring (but with a ruby), Eva Longoria’s jewel also features an oversized halo of diamonds. Our experts estimate the huge rock to be worth a staggering £470,000 ($500,000).

Lady Gaga

Lady Gaga and the ‘Chicago Fire’ star Taylor Kinney were officially together for five years. After four years of dating, Taylor proposed to the singer songwriter on Valentine’s Day with a heart-shaped ring. The couple called off their engagement in July 2016. They split shortly after she got the role in ‘A Star Is Born’.

When Lady Gaga was engaged to Christian Carino in 2018, she wore a pretty pink sparkler that featured a pink sapphire gem centre stone, surrounded by a circle of diamonds that created a flower design. Weighing between 6 and 7 carats, the ring has an estimated value upwards of £300,000.

Kim Kardashian

Kim Kardashian has been married three times – first to Damon Thomas, then Kris Humphries and lastly Kanye West.

Before her debut on ‘Keeping Up With the Kardashians’, the California native tied the knot with producer Damon Thomas when she was just nineteen years old. It’s not known if she ever had an engagement ring.

Professional basketball player Kris Humphries proposed to Kim with a 16.2 carat emerald cut diamond ring with two 1.8 carat diamonds on the side. Made by Lorraine Schwartz, the sparkler has an estimated worth of £1,870,000 ($2 million).

When Kanye West proposed to Kim Kardashian back in 2013, it was in true Yeezy style: with a 15-carat ring worth between £2.3 million ($2.5 million) and £2.8 million ($3 million).

Paris Hilton

Paris Hilton is no stranger to engagements and has had her fair share of failed proposals over the years.

Jason Shaw was the first to propose to the model. Paris was only 21 years old when they got engaged in 2002 and it was short-lived – they never made it down the aisle. Jason proposed with a pear-shaped diamond set in a gold band, which had an estimated value of £500,000 at the time.

Paris’ next engagement was to Paris Kassidokostas-Latsis. He proposed just eight months after they started dating, and Paris famously called off their 2005 wedding. Knowing that he would have to go big if he wanted to marry Paris Hilton, the Greek shipping tycoon offered up 15 spectacular diamond rings of different makes and sizes for her to choose from – she eventually settled on a whopping 24-carat emerald cut, canary diamond ring, worth approximately £3,500,000.

In 2017, Paris started dating actor and model Chris Zylka and fell head over heels for him. A year later in 2018, he proposed on a ski trip in Aspen, Colorado, giving her a 20 carat diamond engagement ring, worth an estimated £1,500,000.

Carter Milliken Reum, author, entrepreneur and venture capitalist went down on one knee on 13th February 2021, at a private island whilst celebrating Paris Hilton’s 40th birthday. Worth £750,000, her emerald cut engagement ring was exclusively designed for her by Jean Dousset – the great-great-grandson of legendary jeweler Cartier.

Mariah Carey

Undoubtedly, the Queen of Bling, Mariah Carey’s love for diamonds is no secret. Her jewellery collection is legendary, with a theme that always says ‘bigger is better,’ and her engagement rings were no exception. Mariah Carey has been married twice and engaged three times.

 Mariah Carey and Tommy Mottola announced their nuptials back in 1993 – the Sony Music Moghul proposed with an emerald-cut diamond, worth £800,000.

Mariah’s second walk down the aisle took place in the Bahamas with actor and comedian Nick Cannon, after a whirlwind six-week romance. Nick proposed on the rooftop of Mariah’s New York City high rise apartment building with a 17-carat pink and white diamond ring from Jacob Arabo of Jacob & Co. Our experts estimate that the head-turning engagement ring holds a value of £1,800,000 ($2,400,000)

Mariah Carey’s third engagement ring from James Packer caused a media storm. Worth a jaw dropping £9,400,000, the magnificent 35-carat rock rivaled all of its counterparts by a mile, and still stands as the largest engagement ring ever worn. After splitting from the Australian billionaire in October 2016, Mariah reportedly sold the ring to a private jeweller.

Jennifer Aniston

Everyone’s favourite friend, Jennifer Aniston has been engaged twice – to actors Brad Pitt and Justin Theroux.

Before popping the question, Brad Pitt worked with designer Silvia Damiani to design Jen’s engagement ring. The center diamond is surrounded by smaller diamonds coiling around it, which is a symbol of eternity. It cost the ‘Fight Club’ actor a whopping £470,000 ($500,000).

When Justin Theroux proposed to Jen, he gifted her an eight-carat, emerald-cut ring, with an estimated value of £470,000 ($500,000).

Kate Hudson

Kate Hudson has worn three sparkling engagement rings – all from musicians: Black Crowes frontman (and ex-husband) Chris Robinson, Muse frontman (and ex-fiancé) Matt Bellamy, and former Chief frontman (and new fiancé) Danny Fujikawa.

Chris Robinson proposed to the actress with a 5-carat Asscher-cut diamond in an Art Deco-style setting.

Kate confirmed her engagement to Matt Bellamy in 2011, showing off a platinum-set ring with an emerald-cut diamond and tapered baguettes on the side. Our experts estimated it to be worth a staggering £180,000 ($200,000).

Longtime boyfriend Danny Fujikawa proposed to Kate after five years of dating with a 10 carat fancy champagne diamond with exceptional clarity. The stunningly unique sparkler is worth £160,000 ($175,000) to £210,000 ($225,000).

Meghan Markle

Before she met Prince Harry, Meghan Markle was married to film producer Trevor Engelson, who she met in 2004. Whilst the two tied the knot in a Jamaican ceremony in 2011, unfortunately they split just two years later in 2013. Trevor proposed with what looks like a round or cushion cut solitaire diamond on a thin platinum or white gold double band, featuring an incredible set of pave diamonds. Our experts valued the ring at an estimated £13,000 ($18,000).

When Prince Harry proposed in 2017, he presented Meghan with a beautiful three stone engagement ring, featuring diamonds from Princess Diana’s jewellery collection. Prince Harry custom designed the £100,000 ring which includes a centre cushion cut diamond, sourced from Botswana – a place that holds a special place in the couple’s hearts. Over 18 months later Meghan made some alterations to the ring, replacing the yellow gold band with a delicate diamond pave band instead.

Avril Lavigne

Avril Lavigne has been engaged three times. Her first fiance was Sum 41’s Deryck Whibley, who proposed to the musician in 2005 with a 4ct diamond solitaire.

Back in 2012, Nickelback lead singer Chad Kroeger proposed to Avril with a whopping 14ct diamond reportedly worth £325,000 ($350,000).

Avril Lavigne got engaged to her long term partner Mod Sun earlier this year. The musician proposed with a custom ring designed by Beverly Hills-based jeweller XIV Karats, featuring a huge heart-shaped diamond set on a narrow pave band. Our experts estimate it’s worth to be around £350,000 to £400,000 depending on the exact quality of the stone.

If you’re looking for some jewellery inspiration, why not take a look at our full collection? Whether you’re after a necklace osome diamond earrings, we’ve got you covered. We also have a vast range of engagement and wedding rings.

If you don’t see anything that takes your fancy, we also offer a bespoke service, where our designers will create a unique piece of jewellery that ticks all the boxes.

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