Celebrity Engagements In 2025 We Don't Think Will Make It To The Altar In 2026

There have been a slew of celebrity engagements in 2025. There was, of course, the news about Travis Kelce and Taylor Swift, who announced their engagement to great fanfare. We were ring-obsessed, naturally, and found out there's a unique explanation behind the cut of Swift's engagement ring. There was also the engagement of Tom Holland to Zendaya, another couple who said yes in 2025 — and an astrologer gave key flags that confirm Tom and Zendaya's fate. It seems like the year for proposals, and with so many engagement rings sparkling on our Instagram feeds, we're curious which of these star couples will make it to the altar in 2026. 

Don't get us wrong. We're not wishing for break-ups. We're only speculating, based on past histories, which of these couples has what it takes to say their vows. Because getting engaged and getting married are two totally different things. Periods of engagement, while joyous, can also be stressful, causing strain on the relationship. In some cases, people end their engagements without breaking up, but in other cases, a breakup is inevitable. Some of these celebrity couples seem less securely connected than others, and we have a speculative list of who might not make it to the altar in 2026. 

After ages of dating, Cristiano Ronaldo and Georgina Rodríguez got engaged in August 2025, with Georgina sharing the news on Instagram. Posting a photo of her huge engagement ring, she wrote in the caption, translated from Spanish: "Yes I do. In this and in all my lives." The two began dating in 2017 and have since welcomed four children, as well as parenting a son from Ronaldo's previous relationship. 

The reason they've earned a place on our list of couples who might not make it to the altar is that their relationship has a lot of red flags. For one, Ronaldo stalled on proposing to Rodríguez. It took him eight years to propose, and many guessed that it wouldn't happen at all, even though the couple had several children. 

Fans really began speculating about their relationship when Ronaldo and Rodríguez moved to Saudi Arabia in 2023, after he started playing for Al Nassr in the Saudi Pro League. Saudi Arabian law technically prohibits unmarried couples from living together, although the law has been relaxed for foreigners. Ronaldo still put off getting engaged, though. It seems like Ronaldo has repeatedly tried to get out of making that final commitment, and we're wondering if the engagement is just a way of buying more time. 

Jake Paul and Jutta Leerdam got engaged in March 2025. They shared the news — and images of her whopping engagement ring — on Instagram, with Paul adding the caption: "We're engaged ... we can't wait to spend forever together." The two met on social media, with Paul reaching out to the Olympic speed skater to invite her on his podcast. They officially began dating in April 2023, and took things from there. 

While they both seem very excited about their engagement, there are some red flags that make us wonder about the couple's likelihood of making it to the altar. For one, Leerdam wasn't into Paul at first. "In the beginning when he hit me up online, I was like, 'No, you look like this arrogant d——-g that thinks he can just get whatever he wants. Well, not me," Leerdam said, per Today. "I never, ever expected to date him, like never." That doesn't sound very promising. Meanwhile, Paul has a long history of controversial behavior, including legal and criminal issues. So between Leerdam's initial lack of interest and Paul's history, we're not totally sure they'll end up getting hitched. 

Molly Smith and Tom Clare of "Love Island: All Stars" got engaged in Dubai in September 2025. The couple shared the news of their engagement, along with a carousel of photos of the elaborate proposal, with their followers on Instagram. The couple also bought a house together and have begun renovating it. Even with all of these events propelling them forward, though, we still have their doubts about the longevity of the relationship. 

In large part, this has to do with the lack of success of relationships that result from reality dating shows. It's not a specific dig at Smith and Clare, but rather a cultural awareness that dating shows have a very low success rate. According to USA Today, most relationships of this nature fizzle quite quickly, and less than 50% of these couples actually end up together long-term — let alone married. 

For Smith and Clare, their relationship faced difficulties out of the gate, largely because of how their connection began. The artificiality of dating shows makes it that much more difficult for the couples to adjust to reality, particularly the realities of an engagement and marriage. So it seems unlikely that they'll make it to the altar. 

Gerry Turner, star of "The Golden Bachelor," proposed to Lana Sutton in October 2025. Incredibly, Turner did not meet Sutton on the show. Rather, Sutton messaged Turner on Facebook, sharing that she lived in Indiana, very close to Turner's home, he revealed in an interview with TMZ. Turner ended up ignoring her first message, but responded to her second message and they met up. Obviously, things went well, because he ended up proposing. 

This relationship seems iffy simply because Turner is so freshly out of a divorce. Turner proposed to Theresa Nist, a contestant on "The Golden Bachelor," and the two had a televised wedding in January 2024. However, after only three months of marriage, the two split, and their divorce was finalized in June 2024. To make matters worse, Turner announced that his memoir, "Golden Years," coming out in November 2025, would spill all the secrets of his brief marriage to Nist. 

"I'm not worried; I think she should be worried," he told Us Weekly in an interview. While everyone has a right to share their story, it seems a little petty to publish a memoir making jabs at his ex-wife. Not only that, it also seems like Turner was on the rebound when Sutton reached out, making us wonder about the stability of his engagement.