Celebrity Engagements; From “Yes” to “Thank You, Next

Jul 17, 2022 | New York Prenuptial Agreements, Relationships, Wedding

Hollywood is full of break-ups, make-ups, and your occasional star-studded wedding. Celebrities are no stranger to whirlwind romances. Sometimes, it truly is love at first sight, and the pair makes it all the way to the altar. But other times, the couple never sets foot on the aisle, much less walks down it. Here are celebrity engagements that went wrong. 

Eight Celebrities Engagements That Didn’t Turn Out Great 

Ariana Grande and Pete Davidson 

Ariana Grande and Pete Davidson are among the most recent celebrity couples to call it quits. The duo officially romantically met in May 2018 after they had recently called it quits with their long-time partners. Ariana had dated the late Mac Miller for a couple of years before breaking up after Coachella, while Pete had been dating his girlfriend, Cazzie David, for a similar length of time. 

As soon as the celeb’s split from their significant others, they quickly became wrapped up in a whirlwind romance. Just weeks after their first date, they were officially an item. Not even five weeks later, on June 3, 2018, Ariana stepped out to show off her engagement ring. Multiple outlets reported that Ariana and Pete were engaged. Seemingly confirming the news, the duo moved in with one another in mid-June 2018. 

The couple continued to post cute Instagram pictures and be spotted hanging out with one another until October when photographers pointed out that Pete had recently covered up a tattoo dedicated to his fiance. By October 14, 2018, the news was out; the engagement of Ariana Grande and Pete Davidson was no more. Their fast and furious five-month relationship had come to an end. 

Johnny Depp and ….

Sherilyn Fenn

Sherilyn Fenn, an actress and author, met Johnny on a film set in 1985. They became an on-again-off-again couple that strove to remedy their spotty dating history with marriage. However, their engagement was short-lived and officially ended their three-year relationship. 

Jennifer Grey

In the late eighties, Johnny and Jennifer, the Dirty Dancing starlet, were a “thing.” It’s unclear when they began dating, but the pair were engaged for a year in 1989, after which they separated. 

Winona Ryder

Winona Ryder was way less low profile than Jennifer. After meeting in 1990 at a movie premiere, Johnny popped the question after five months of dating. Three years later, Johnny proved his “Winona Forever” tattoo wrong when the pair broke off their engagement. 

Sean Penn and Charlize Theron

Sean and Charlize were friends for years before they became romantically involved, which took some by surprise. Sean had just gotten out of a sixteen-year relationship with his ex-wife Robin Wright before meeting fellow silver-screen-star Charlize; who had been separated from her past beau, Stuart Townsend, for some time. 

In December 2013, they stepped out on the red carpet together. Charlize reportedly called the ruggedly handsome Sean “the love of her life”.  It was rumored that the couple became engaged in 2015, after a secretive trip to Paris. However, rumors were quickly followed by news of the pair splitting. However, Charlize claimed in an interview that she did nothing more than date Sean, claiming that she was “never going to marry him” because marriage is something that’s “never been important” to her. 

Hayden Christiansen and Rachel Bilson

Hayden and Rachel were co-stars in the 2008 movie Jumper. The pair struck up a relationship off-screen and began dating. In late 2008, in December, the actors were reportedly engaged. However, after two years of planning their nuptials, the wedding was off, only to rekindle their relationship in November 2010. 

While they never moved forward with their engagement, the pair welcomed a daughter together in October 2014. In 2017, on the cusp of their ten-year “dating” anniversary, the duo officially and wholly split. 

Lady Gaga and Taylor Kinney

Actor Taylor Kinney was once engaged to pop star princess Lady Gaga. In July 2011, the couple met on Gaga’s “Yoü & I” music video set. He was an actor in the video and apparently knew it was love at first sight, going off script by kissing Gaga as soon as the cameras started rolling. It took a little longer for the singer to warm up to the idea, but she came around. 

One month later, they were reportedly “hooking up,” finally breaking their silence two months after being spotted on a romantic getaway. On Valentine’s Day in 2015, Kinney proposed with a breathtaking heart-shaped ring. Things came to a crashing end in July 2016 when it was reported that straight-laced Kinney, and wild-at-heart Gaga had broken up after five years together. 

Olivia Wilde and Jason Sudeikis

You may not have even realized that Olivia and Jason were only engaged. The pair was together for over a decade after meeting at an SNL after-party in 2011. Six months after their meeting, they were romantically linked, and after two years of dating in 2013, Sudeikis popped the question. But before the couple reached the altar, they welcomed their first child, Otis, in 2014. 

In April 2016, Sudeikis acknowledged that they had been engaged for three years and said they would still remain engaged without getting married, seemingly forever. A month after his comment, Olivia announced she was expecting their second baby, born in October 2016. Jason’s prediction came true in November 2020, just not as he probably expected. After seven years together, Olivia and Jason called it quits. 

Rob Kardashian and Blac Chyna

Rob Kardashian and Blac Chyna may be one of the least talked about couples when it comes to the Kardashian family. Still, they did have some romantic troubles of their own. Despite the disapproval from the Kardashian family, their relationship quickly heated up after announcing their budding romance on social media in 2016. 

Just one month after becoming Instagram official, Blac Chyna was sporting a massive engagement ring. Unfortunately, only weeks after proposing, Rob promptly deleted all his photos, and Blac Chyna confirmed they split. Fortunately, the break was temporary, and the ring was back on by April 2016, just in time for the couple to announce their impending little one in May. July saw another separation, at least until they welcomed their daughter in November 2016. The pattern continued, on-again and off-again, until late 2018, when things changed dramatically, and the duo parted ways for good. 

Ben Affleck and Jennifer Lopez

Did you know that Bennifer is actually a blast from the past? The actor and singer first became involved in 2001 while they were both on the set of the film Gigli. In November 2002, Affleck proposed with a stunning pink diamond ring. Not long after, Ben was spotted in J Lo’s iconic “Jenny From the Block” music video. They continued to make red carpet appearances as a couple, and Jennifer’s pink diamond ring even started an engagement trend! 

Sadly, days before their wedding in September 2003, they called off their impending nuptials. While they only intended to postpone their marriage due to a media frenzy, it seems like the relationship just wasn’t meant to be, and they separated officially in early 2004. That is until May 2021, when the starlets appeared to be rekindling their romance! In April 2022, the lovebirds shared their (second) engagement with the world! Hopefully, this time it will be smooth sailing until they say, “I do.” 

Still curious?

It seems that whenever a celebrity couple goes official with their engagement, an announcement of their prenuptial agreement is sure to follow. And for a good reason. Celebrities, in particular, stand to lose quite a lot should a split occur. Though you don’t have to be famous to have a prenuptial agreement! 

Interested in wanting to learn more about prenups in pop culture? Check out what’s going on with 90 Day Fiance this season here!

When considering or getting engaged, conversations around a premarital contract can help protect you in the case of future separation. It’s an essential agreement, whether you have substantial assets or debt. They’re not just for divorce, either. In one way or another, all marriages end, even if it results from a spouse dying. Knowing your rights and responsibilities regarding wealth and assets upfront is a valuable investment in your relationship, whether you’re a celebrity or not. Check out how HelloPrenup works to save you time and money while creating a prenup from the comfort of your own home! 

You are writing your life story. Get on the same page with a prenup. For love that lasts a lifetime, preparation is key. Safeguard your shared tomorrows, starting today.
All content provided on this blog is for informational purposes only. HelloPrenup, Inc. (“HelloPrenup”) makes no representations as to the accuracy or completeness of any information on this site. HelloPrenup will not be liable for any errors or omissions in this information nor for the availability of this information. These terms and conditions of use are subject to change at any time and without notice. HelloPrenup provides a platform for contract related self-help. The information provided by HelloPrenup along with the content on our website related to legal matters (“Information”) is provided for your private use and does not constitute legal advice. We do not review any information you provide us for legal accuracy or sufficiency, draw legal conclusions, provide opinions about your selection of forms, or apply the law to the facts of your situation. If you need legal advice for a specific problem, you should consult with a licensed attorney. Neither HelloPrenup nor any information provided by Hello Prenup is a substitute for legal advice from a qualified attorney licensed to practice in an appropriate jurisdiction.


Recent Posts

Will A Prenup Hold Up In Court?

A prenuptial agreement, often referred to as a prenup, is a legal contract signed by couples before marriage that outlines many different topics, such as how assets will be divided in the event of divorce or death and alimony. With the rise in popularity of prenups,...

Prenup vs. Postnup

Alright, folks, it's time to tackle one of the burning questions we get asked a lot here at HelloPrenup. Cue the drumroll... What's the difference between prenuptial agreements, a.k.a. "prenups," versus postnuptial agreements, a.k.a. "postnups"? Well, they're pretty...

Does Patrick Mahomes Have A Prenup?

Patrick Mahomes signed the biggest NFL contract in history in 2020–a whopping $450 million over 10 years. With his recent marriage to Brittany Matthews (now Brittany Mahomes), it’s understandable why there’s been so much interest in their prenup and whether or not...

Does J.Lo Have A Prenup?

Hold onto your hats, folks, because the hottest topic in Hollywood right now is none other than the rekindled romance between Jennifer Lopez and Ben Affleck. But amidst the whirlwind of their highly-publicized love affair, there's one question burning brighter than...

Ready to join the thousands of couples completing their prenup?