25+ Most Valuable Celebrity Engagement Rings of All Time

Occasion: J.Lo and Ben Affleck’s second engagement // Value of Ring: Estimated value of up to $10 million

J.Lo and Ben Affleck, known as Bennifer, showed the world that second chances really do happen. Bennifer’s romance first started in December of 2001 and Ben proposed a year later with a 6.1-carat pink, solitaire ring! However, just days before their wedding, the couple called it quits.

Fast forward to 2021, Bennifer rekindled their relationship. In April 2022, Ben proposed with a rare 8.5-carat, green diamond ring. The couple tied the knot in Vegas and later had another wedding, celebrated with friends and family at Ben’s Georgia home.

Occasion: Blake Lively and Ryan Reynold’s engagement // Value of Ring: $2 million

Blake and Ryan are undoubtedly one of Hollywood’s greatest power couples. Despite first meeting in 2010, the pair went on a double date a year later. However, they were on this double date with different partners… awkward. In 2012, Reynolds proposed with a 12-carat diamond. The ring is valued at $2 million.

Their wedding was described as picture-perfect, however, a sparkler burnt a hole in Blake’s gown. Reynolds turned the heartbreaking incident into an endearing memory which has now become Blake’s favorite part of her dress. The couple has three daughters, and they recently announced that they’re expecting their fourth child.

Occasion: Heidi Klum and Seal’s engagement // Value of Ring: $150,000

Heidi met Seal in the lobby of a hotel in 2004. Seal wasted no time and proposed with a 10-carat, canary diamond ring. Seal planned an elaborate proposal where he took Klum to the Canadian Rockies. As expected, there were rose petals laid out to set the mood… inside of an igloo.

The couple married in Mexico, and they have three children together, with Seal even adopting Klum’s first child from a previous relationship. Every year, the couple renewed their vows as a romantic tradition. Unfortunately, though, the model and singer separated in 2012 before officially divorcing in 2014. The two remain close friends, however, and continue to co-parent their children together.

Occasion: Serena Willams and Alexis Ohanian’s engagement // Value of Ring: $2 million

Serena met Alexis by chance in 2015 while having breakfast in Rome. Alexis attended the Italian Open the day he met Serena and she invited him to the upcoming French Open. He flew to Paris for the weekend to watch her play and the rest is history.

In 2016, Alexis proposed at the very hotel they first met in. He popped the question with a 12-carat emerald-cut diamond ring. A month after the proposal, the couple found out that they were expecting. With three outfit changes and a star-studded guest list, Williams and Ohanian tied the knot in 2017 — and it was apparently the wedding of the year.

Occasion: Katie Holmes and Tom Cruise’s engagement // Value of Ring: $250,000

In 2005, Katie Holmes and Tom Cruise made their relationship public while in Rome together, although many speculated it was a publicity stunt. Just less than eight weeks after meeting, Tom proposed while the pair were enjoying a romantic dinner in the Eiffel Tower. He presented Katie with a five-carat oval-shaped ring.

Shortly after getting engaged, the Hollywood stars announced that they were expecting a child. Cruise even purchased a sonogram machine to track the development of the baby. The couple wed in a lavish ceremony in Italy, where many A-list celebs were in attendance. After six years of marriage, Katie filed for divorce.

Occasion: Paris Hilton and Carter Reum’s engagement // Value of Ring: $5 million

Despite knowing each other for 15 years the couple only started dating in 2019 when Paris was invited to their Thanksgiving dinner. While opening up about her relationship, Paris was quick to credit the lockdown, as it meant she got to spend her time with her beau.

To celebrate Paris’ 40th birthday, Hilton and Reum vacationed on a private island. Carter proposed with a 24-carat diamond ring. Unsurprisingly, these two lovebirds had an extravagant wedding in November of 2021. With three outfit changes and a six-foot-tall wedding cake, the duo spared no expense to throw a luxurious and memorable wedding.

Occasion: Catherine Zeta-Jones and Michael Douglas’ engagement // Value of Ring: $1 million

In 1998, Catherine Zeta-Jones and Michael Douglas were introduced to each other by a mutual friend. Just three months later, the couple announced that they were expecting. On New Year’s Eve a month later, Douglas proposed with a vintage-style, 10-carat diamond ring.

The couple got married in New York City and celebrated in what was a lavish affair. They reportedly spent an estimated $1.5 million on their wedding. Then again, we guess it was worth it considering that they’ve now been married for 21 years. That’s almost as long as their 25-year age gap! Fun fact — did you know that Catherine and Michael actually share the same birthday?

Occasion: Kim Kardashian and Kanye West’s engagement // Value of Ring: $3 million

Kim has had her fair share of experience with rings and weddings. In 2011, Kanye invited Kim to watch his fashion show in Paris, which is when the couple officially started dating.

Kanye proposed on Kim’s 33rd birthday in 2013 with a 15-carat diamond ring. In 2014, West and Kardashian had a European wedding that began in Paris and ended in Italy. Their nuptials ended up costing $2.8 million!

Occasion: Beyoncé and Jay-Z’s engagement // Value of Ring: $5 million

Beyoncé and Jay-Z are one of the most iconic celebrity couples to date. The two first met in 2000 while on the same flight to Cancun, and they began dating a year later. They secretly got engaged and married in 2008. Queen Bey received a 24-carat diamond engagement ring for the special occasion!

In 2011, during one of her concerts, Beyoncé announced that they were expecting for the first time. If that wasn’t historical enough, Bey turned to Instagram to announce her second pregnancy with a stylish photoshoot.

Occasion: Anna Kournikova and Enrique Iglesias’s engagement // Value of Ring: $2.5 million

The couple first met in 2001, on the set of Enrique’s music video. Rumors began circulating that the couple was engaged when Anna was seen wearing an 11-carat, canary ring. However, there’s little known of when they got engaged — or if they’re even married, for that matter.

Anna has said before that marriage isn’t important to her and that she’s in a happy relationship. In 2017, the couple welcomed twins — and in 2020, they added another daughter to the family. Considering how private the celeb couple is about their relationship, it comes as no surprise that the same applies to their family and children.

Occasion: Mariah Carey and James Packer’s engagement // Value of Ring: $10 million

Mariah Carey and James Packer ended their relationship almost as quickly as it began. The pair first met in July of 2014, and they instantly hit it off. In 2015, they made their first public appearance as a couple.

In January of 2016, the couple got engaged, during which Mariah received a massive 35-carat diamond ring! Mariah teased fans about her wedding plans. Soon after they announced their engagement, though, Carey and Packer split.

Occasion: Elizabeth Taylor’s gift from Richard Burton // Value of Ring: $1 million

Elizabeth and Richard met in 1954 at a Hollywood party, though nothing transpired between the two at the time. Nine years later, they reunited as costars on the set of Cleopatra. Despite the fact that both stars were married during filming, their attraction grew and they went on to have one of the most controversial Hollywood affairs. Burton proposed in 1964 and they tied the knot that same year after both divorces were finalized.

They were then together for 10 years, before divorcing in 1974. In 1975, they remarried before splitting again just a year after that. Although Taylor married Burton twice, she never actually got an engagement ring. In fact, Taylor received an emerald brooch when Burton first proposed, which she pinned to her marigold wedding dress. Five years into their first marriage, Burton presented Taylor with the one-million-dollar stone that was renamed the Taylor-Burton diamond.

Occasion: Kirsten Dunst and Jesse Plemons’ engagement // Value of Ring: $80,000

Kirsten and Jesse met while on set in 2015. In 2017, Kirsten was spotted by fans wearing a diamond ring on *that* finger and it was later confirmed that the actors were indeed engaged. Jesse proposed with a three-carat diamond that cost him $80,000.

In 2018, the couple announced that they were expecting their first child together. The couple welcomed their second child in 2021, though they only tied the knot in July 2022 in a beautiful ceremony held at a luxury resort in Jamaica.

Occasion: Simone Biles and Jonathan Owens’ engagement // Value of Ring: $300,000

Simone Biles met her now-fiancé Jonathan on the dating app Raya, where the gymnast actually made the first move. In August 2020, the couple went public with their relationship and became Instagram official.

To celebrate their first anniversary, the couple traveled to Belize and kept all their fans up to date with their love-packed vacation on social media. Jonathan popped the question in February 2022 with an eight-carat diamond ring.

Occasion:Britney Spears and Sam Ashgari’s engagement // Value of Ring: $70, 000

Britney and Sam met in 2016, although he almost blew his chances with the pop star when he cracked a joke that went horribly wrong. Luckily for Sam, Britney overlooked that awkward moment and they exchanged numbers.

The couple finally announced their engagement on Instagram in September 2021, in which Sam had proposed with a four-carat diamond ring that he helped design. Britney and Sam tied the knot in June 2022 surrounded by A-list stars like Selena Gomez, Madonna, and Paris Hilton.

Occasion: Lily Collins and Charlie McDowell’s engagement // Value of Ring: $100, 000

Lily described their initial meeting as love at first sight and knew that one day she would be his wife. The couple made their relationship Instagram official in August 2019. Charlie didn’t wait long to pop the question. In fact, it was only a year after they first went public with their relationship.

Charlie proposed while they were on a road trip through Mexico with a unique four-carat diamond ring. They wed in September 2021 in Colorado in what was an intimate, rustic-themed wedding. Lily stunned in a gorgeous long-sleeved, hooded lace gown by Ralph Lauren

Occasion: Nicola Peltz and Brooklyn Beckham’s engagement // Value of Ring: $2 million

Dating rumors between Nicola and Brooklyn sparked in October 2019 when the pair was seen having dinner after attending Leonardo DiCaprio’s Halloween party. These two are incredibly open about their relationship, as evidenced by their social media accounts, which are filled with loved-up posts and captions.

After just six months of dating, Brooklyn popped the question with a five-carat emerald-cut diamond ring. Nicola took it upon herself, however, to upgrade the ring — which is now an eight-carat oval diamond worth two million dollars. In April 2022, the couple tied the knot in a multi-day celebration.

Occasion: Sophie Turner and Joe Jonas’ engagement // Value of Ring: $20,000 – $58,000

The two were first spotted in 2016 locking lips at a Kings of Leon concert — though they only confirmed their relationship in January of 2017. In October 2017, Sophie was caught off-guard when Joe popped the question with a three-carat, pear-shaped diamond ring.

The couple had a white chapel wedding in Vegas, which obviously included an Elvis impersonator. Although the couple said their “I do’s” in Vegas, they held a more formal second wedding in the south of France with all their family and friends. The couple has since welcomed two daughters.

Occasion: Chrissy Teigen and John Legend’s engagement // Value of Ring: $150,000 – $200,000

Here we have yet another Hollywood power couple! The two first met in 2006. During an interview, John revealed that he tried to end the relationship once — but Chrissy was having none of it and point blank said “no.” They were back on a half hour later. In 2011, John proposed in the Maldives with a six-carat diamond ring.

Their wedding was held in Lake Como, where the couple had shared their first vacation together. For the big day, Chrissy wore three different custom Vera Wang gowns. And not only did John sing during the ceremony, but so did the incredible Stevie Wonder! Since then, Teigen and Legend have welcomed a daughter and a son. They’re expecting another child in 2022.

Occasion: Gwyneth Paltrow and Brad Falchuk’s engagement // Value of Ring: $500,000

Gwyneth and Falchuk met in 2010 when the actress made a guest appearance on the hit show Glee, which Brad was co-producing. They began dating in 2014 and got engaged two years later when Brad proposed with a 13-carat sapphire ring. They exchanged vows in an intimate wedding in the Hamptons.

In 2021, Gwyneth shared that she feels like she’s still in the ‘honeymoon phase’ of their relationship and went on to talk about a tradition they started while dating. According to the blonde bombshell herself, “When Brad was just my boyfriend, I started a tradition of making him breakfast every Saturday morning.” Apparently, it was a way for Gwyneth to disconnect from the other stresses in her life and focus on Brad. They’re called #boyfriendbreakfasts to this day!

Occasion: Katy Perry and Orlando Bloom’s engagement // Value of Ring: $5 million

Dating rumors began flying in 2016 when Katy Perry and Orlando Bloom were spotted looking flirty at the Golden Globes afterparty — where Katy initiated a dance-off with Orlando. Despite a few breakups, the couple announced their engagement in 2019. Orlando popped the question on Valentine’s Day during a helicopter ride.

Katy received a stunning four-carat pink diamond. Before long, Katy teased fans with pregnancy rumors while she was cradling a baby bump in one of her music videos. She later confirmed that they were indeed expecting! They welcomed their daughter, Daisy Dove Bloom, in August 2020.

Occasion: Katherine Schwarzenegger and Chris Pratt’s engagement // Value of Ring: $350,000

Actor Chris Pratt and now-wife Katherine Schwarzenegger met at church. According to Pratt himself, “It was a lot of kismet, and a lot of connections, but that was where we met.” They began dating in 2018 and they were engaged a year later. Chris proposed with a five-carat diamond ring.

Shortly after announcing their engagement, the two married in a small ceremony celebrated with friends and family — including Pratt’s 6-year-old son Jack, whom he shares with ex-wife Anna Faris. Schwarzenegger and Pratt welcomed their first child as a couple in 2020 and announced in December 2021 that they were expecting their second child.

Occasion: Jada and Will Smith’s engagement // Value of Ring:$250,000

Jada and Will first met during a Fresh Prince of Bel-Air audition but only began dating in 1995. Will proposed with a 12-carat diamond ring two years later, in 1997. The couple got married in a private wedding in Baltimore and welcomed their first child soon after, in 1998.

The couple welcomed their second child in 2000. Over the years, they’ve remained transparent about the struggles they’ve had in their marriage. During an interview in 2013, Jada shared that the two even have an open marriage. Despite the challenges they’ve faced, the couple remains married to this day.

Occasion: Priyanka Chopra and Nick Jonas’s engagement // Value of Ring:$200,000

Priyanka initiated the first move in the relationship and slid into Nick’s DMs back in 2016. The two made their relationship official in 2018. It wasn’t long after that engagement rumors started when the two were seen wearing matching gold rings. In July of 2018, Nick shut down a Tiffany store to choose the five-carat diamond ring that he’d propose with.

Their wedding was a three-day celebration that combined both their Christain and Hindu marriage traditions. Since then, they’ve been living in marital bliss. They even welcomed daughter Malti Marie Chopra Jonas via surrogacy in January 2022.

Occasion: Amal and George Clooney’s engagement // Value of Ring:$750,000

George was first introduced to his now-wife by a mutual friend. It turns out that George’s buddy was heading over for dinner when he called to ask if he could bring another guest. Before Amal even arrived, George got a call from his agent, who predicted that the actor would one day marry this unexpected guest. Naturally, the two had an instant connection when they met and they spent the whole night talking.

George proposed in 2014 with a romantic homecooked dinner and a seven-carat diamond ring. The two married in September of 2014 in what was described as the biggest celebrity wedding since Prince William and Kate’s wedding three years prior. A few years later, in 2017, the duo welcomed twins.

Occasion: Kate Middleton and Prince William’s engagement // Value of Ring:$500,000

Speaking of the royals, William and Kate first met in college in 2001. They were friends for over a year before it blossomed into romance. Though the duo dated for most of their college careers, they decided to split after graduation in order to learn more about themselves. Soon after, though, they reunited during the summer of 2007.

Prince William proposed in 2010 with late mother, Princess Diana’s 12-carat sapphire ring that has an estimated value of $500,000. The royal couple tied the knot in 2011 at Westminster Abbey in London. The royals announced they were expecting their first child in 2012, and welcomed two more children after that, in 2015 and 2018.

Occasion: Eva Longoria and José Baston’s engagement // Value of Ring:$500,000

In 2013, the two were set up by mutual friends, but it was said that the spark wasn’t there initially. When the same friend re-introduced them six months later there was an instant connection. José popped the question while they were in Dubai, he proposed with a six-carat ruby diamond.

The two wed in 2016 in Mexico in a lavish ceremony that included a star-studded guest list. Eva’s dress was designed by her best friend, Victoria Beckham. In 2018, the couple welcomed their first child together, making this José’s fourth child.

Occasion: Hailey Baldwin and Justin Bieber’s engagement // Value of Ring: $500,000

Hailey met Justin in a brief meet-and-greet in 2009. In 2015, they were spotted kissing while celebrating New Year’s together. Despite their breakup, they reunited in 2018. In July 2018, Justin proposed with a 10-carat diamond ring.

In September 2018, the couple had a legal civil ceremony and Hailey made it Instagram official by changing her handle to @HaileyBieber. A year later, the couple held a wedding ceremony in South Carolina where Hailey wore an iconic veil that had “Till Death Do Us Part” embroidered on it.

Occasion: Sofia Vergara and Joe Manganiello’s engagement // Value of Ring: $750,000

Sofia was engaged when she first met Joe in 2014. Joe reached out to Modern Family co-star Jesse Tyler Ferguson, asking for her number when he heard she was single. The two went on a date and although Sofia spent that entire time listing reasons why they wouldn’t work out, love prevailed — as it always does!

Just six months later, Joe was spotted ring shopping. Out of fear that his proposal would be ruined by paparazzi, he popped the question in their hotel suite while they were on vacation for the Christmas holiday. Not only did he ask the question in Spanish, but he also presented Sofia with a five-carat diamond ring. They wed in Palm Beach in 2015.

Occasion: Ciara and Russell Wilson’s engagement // Value of Ring: $2 million

Russell first met Ciara in 2015 at a basketball game. Russel sealed the deal in 2016 with a beach proposal in Seychelles with a 16-carat diamond ring. They tied the knot just a few months later in a private wedding in England. The couple welcomed their first daughter together in 2017.

In 2020, Ciara and Wilson took to Instagram to announce they were expecting another child. In 2022, while Ciara was co-hosting an episode of The Ellen DeGeneres Show, Russell took the opportunity to propose for a second time and ask that they have another baby together. After a good laugh, Ciara agreed. How cute!

Occasion: Hilary Duff and Matthew Koma’s engagement // Value of Ring: $80,000

After hitting it off in the studio while collaborating on an album in 2015, Hilary Duff and Matthew Koma made their debut in 2017. After taking a short break, the couple rekindled their romance in 2018. Soon after, they turned to Instagram to announce that they were expecting. In October 2018, they welcomed their first child together, Banks.

In 2019, the couple went for a walk where Matthew gave Hilary a book he made about their relationship. At the end of the book, there was a secret compartment that held a four-carat diamond ring that cost $80,000. Months later, the couple got married in an intimate ceremony.

Occasion: Kourtney Kardashian and Travis Barker’s engagement // Value of Ring: $1 million

Kravis confirmed their relationship in 2021 after a few months of dating. The couple pack on the PDA both on social media, as well as in the public eye. Travis finally popped the question in October 2021 on the beach, where the duo was surrounded by hundreds of red roses.

Kourtney received a 12-carat diamond ring. In April 2022, the couple got hitched in Vegas. In May, Kravis had a lavish ceremony in Dolce and Gabbana’s villa in Italy, where they celebrated with all of their family and friends.

Occasion: Gabrielle Union and Dwyane Wade’s engagement // Value of Ring: $1 million

The two began dating in 2009. After a short break, they announced their engagement in 2013. After touring around the construction site of their house, Gabrielle found Dwyane’s sons from his previous marriage holding a sign saying “Will you marry us?” Originally, Gabrielle thought it was a joke, as the kids had asked the same question many times before.

Dwyane proposed with an 8.5-carat diamond ring. In 2014, the couple got married in an intimate wedding in Florida. In 2017, Gabrielle publicly shared her fertility struggles and how she had suffered many miscarriages. In 2018, however, Union and Wade welcomed their first daughter together via surrogacy.

Occasion: Cardi B and Offset’s engagement // Value of Ring: $500, 000

In Jaunary 2017, Cardi B and Offset collaborated and released a track together. A month later, they went on their first date in which Offset took Cardi to the Super Bowl! Iconic, right? In 2017, Cardi publicly dropped a huge engagement hint to her beau. Months later, Offset proposed to Cardi on stage with an eight-carat diamond ring.

In 2017, the musicians secretly wed — and a year later, they welcomed their first child. In September 2020, Cardi filed for divorce, which was later called off. In June 2021, Cardi shared a stunning maternity photoshoot that confirmed the couple was expecting their second child.

Occasion: Megan Fox and Machine Gun Kelly’s engagement // Value of Ring: $300, 000

Megan and her husband at the time were already separated when rumors began circulating in early 2020 about a possible romance between her and Machine Gun Kelly (MGK). Rumors grew when Megan starred in MGK’s music video. The unconventional duo confirmed their relationship in June 2020.

In January 2022, the couple announced their engagement. MGK designed a ring made of two six-carat diamonds. The ring resembles two parts that came together as one — and it features a diamond (MGK’s birthstone), as well as an emerald (Fox’s birthstone). It’s no secret that the ring, which features thorns, caused some controversy when fans first learned of the engagement.

Occasion: Jennifer Lawrence and Cooke Maroney’s engagement // Value of Ring: $150, 000 – $200, 000

The couple started dating when a mutual friend introduced Jennifer and Cooke in 2018. In February of 2019, the duo got engaged. While little details are known about the proposal, we do know that Cooke got his now-wife a five-carat diamond ring.

The lovebirds made it official in October 2019 at the Belcourt of Newport mansion in Rhode Island. According to sources, the actress and art dealer only left their wedding at 5:30 am after partying the whole night, before subsequently jetting off to Indonesia for their honeymoon. The couple welcomed their first child together in 2022.

Occasion: Reese Witherspoon and Jim Toth’s engagement // Value of Ring: $200, 000

Reese Witherspoon met Jim Toth in 2010 at a friend’s house, and they hit it off right away. In December, less than a year later, the couple got engaged. Jim proposed with a four-carat diamond ring. Shortly after, the couple wed on their ranch.

In 2012, the couple announced they were expecting their first child together. They welcomed a son that same year, in September. Reese shared a selfie on Instagram in March 2022 to commemorate their 11 years of marriage.

Occasion: Ariana Grande and Dalton Gomez’s engagement // Value of Ring: $350, 000

After ending her engagement with Saturday Night Live star Pete Davidson in 2018, Ariana kept her new relationship with Dalton private. The couple went public with their relationship in May 2020. Ariana went on to share moments of their relationship on her Instagram, including posts for both of their birthdays.

Dalton proposed just before Christmas in December of 2020, he designed and customized Grande’s ring, which features a five-carat diamond and a pearl. The pearl was from a ring that her grandmother had gifted her. In May 2021, they exchanged vows in an intimate wedding.

Occasion: Scarlett Johansson and Colin Jost’s engagement // Value of Ring: $450,000

In 2006, Scarlett was hosting Saturday Night Live for the first time. Her now-husband, Colin, had just become a writer on the show. Scarlett hosted SNL quite a few times but it wasn’t until 2017, at an SNL afterparty, that the two were romantically linked.

Colin proposed in 2019 with an 11-carat pear-shaped diamond. Months later, while hosting SNL again, Scarlett joked about how Colin would get fired if the show didn’t go well and thanked SNL for being the place she met the love of her life. The couple wed in 2020 and welcomed their first child a year later.

Occasion: Yvette Prieto and Michael Jordan’s engagement // Value of Ring: $1 million

This ultra-private couple hasn’t shared much about their relationship, but this is what we do know. Yvette and Michael first met on the dance floor of a Miami club in 2007 and moved in together two years later. On Christmas Eve of 2011, basketball legend proposed with an estimated 10-carat diamond ring.

If a million bucks wasn’t a lot to begin with, it’s said that their 2013 lavish wedding cost $10 million! The wedding included 300 of their closest friends and family members — plus, Usher and Robin Thicke both performed at the wedding. In February of 2014, the couple welcomed twin daughters.

Occasion: Victoria and David Beckham’s engagement // Value of Ring: $1.3 million

Victoria said she knew David was the one when they first met in 1997. David proposed in 1998 with a three-carat diamond ring. Over their 22 years of marriage, this is one of many rings that she has received — 1 of 15, to be exact. The couple welcomed their first son in March 1999 and wed four months later.

The bombshell couple went on to have another two sons in 2002 and 2005, and welcomed a daughter in 2011. The latest ring Victoria received was in 2018, a square-cut yellow diamond worth a whopping $1.3 million.

Occasion: Angelina Jolie and Brad Pitt’s engagement // Value of Ring: $1 million

Brad and Angelina first met in 2004 while filming the movie Mr. and Mrs. Smith. Brangelina became official in 2005. In 2006, Brad legally adopted Angelina’s two children, whom she had adopted from Cambodia and Ethiopia. In May of that year, the couple welcomed their first child together.

In 2007, the couple adopted their fourth child from Vietnam and welcomed a set of biological twins in July of 2008. After seven years, Brad popped the question with a 16-carat diamond ring, which he designed himself. In 2014, the couple had a very intimate wedding. Soon after their second wedding anniversary, however, Angelina filed for divorce.

Occasion: Jessica Biel and Justin Timberlake’s engagement // Value of Ring: $100,000

While snowboarding together in Utah in 2007, Jessica Biel and Justin Timberlake sparked up a romance. After a brief break in the relationship in 2011, the couple came back stronger than ever and announced their engagement. Justin proposed in December of 2011 while on their annual vacation to Montana, with a six-carat diamond.

The two married in a low-key wedding in Italy in October of 2012. In 2015, the celebs welcomed their first child — and had their second in 2021. Jessica recently posted a series of photos of the couple on Instagram in celebration of their 10th wedding anniversary.

Occasion: Emily Blunt and John Krasinski’s engagement // Value of Ring: $100,000

A mutual friend introduced this beloved couple back in November 2008. Less than a year later, John proposed to Emily with a three-carat diamond ring. The two wed in 2010 at George Clooney’s estate in Lake Como. The couple welcomed their first child in February 2014.

In 2016, the A-list celebs welcomed their second child together. A year later, the two announced they’d be creating a film together, A Quiet Place. After much critical acclaim and award nominations — including a win for Emily — Blunt and Krasinski announced they’ll be making a sequel.

Occasion: Bella Thorne and Benjamin Mascolo’s engagement // Value of Ring: $150,000

Bella and Benjamin first met at Coachella in April of 2019 and made their relationship Instagram official just months later. Due to the pandemic, the couple had to spend months apart and reunited in July 2020. A few months later, the two became co-stars in Benjamin’s first film.

After almost two years of dating, Ben popped the question with a four-carat, pear-shaped ring. Unfortunately, in June 2022, Bella shared on her Instagram that she had ended their relationship and requested privacy during this time.