Hollywood Couples Fans Think Will Get Engaged Before 2027

Between soft launches, matching red carpet looks, and the occasional “moving in together” clue, fans have already picked their favorites for the next round of celebrity engagements. With Taylor Swift, Zendaya, Dua Lipa, and Miley Cyrus already off the market for 2026, attention has shifted to the couples still in the “any day now” phase. Here’s who fans think is closest to popping the question before 2027 rolls around, and why.

Klay Thompson and Megan Thee Stallion

How Public They’ve Gone

Thompson and Megan went from soft launch to full red carpet debut within months, with Megan showing up courtside to cheer him on at Dallas Mavericks games. A photo Megan posted just before Halloween, showing the two holding what looked like a shared set of keys, immediately had fans speculating they’d moved in together.

Why Fans Think a Proposal Is Close

• Prediction market Kalshi Culture puts the odds at a 73% chance the couple gets engaged before 2027.
• The pace of their relationship, public debut, courtside appearances, and the “keys” post, has moved quickly compared to how private both stars have historically been.
• Neither has confirmed exactly how long they were together before going public, which fans read as a sign the relationship is more established than it first appeared.

Kylie Jenner and Timothée Chalamet

A Slow-Burn Rollout

Unlike Thompson and Megan, Jenner and Chalamet have taken their time going public. It took more than two years after dating rumors first started for the two to make an official red carpet debut together, and fans have tracked nearly every step of that slow rollout since.

Signs Fans Are Watching

Jenner accompanied Chalamet to the David Di Donatello Awards in Rome in May 2025, an early sign the two were getting comfortable being seen together, and six months later they coordinated matching orange outfits at the “Marty Supreme” premiere. Despite breakup rumors and public scrutiny along the way, the relationship has reportedly only gotten more serious, which is why fans are betting on a proposal landing sometime in 2026 rather than further out.

Ariana Grande and Ethan Slater

A Complicated Start

Grande and Slater met on the set of “Wicked” in December 2022 while both were married to other people. Their respective splits, from Dalton Gomez and Lilly Jay, were confirmed within days of each other in mid-2023, and the two reportedly moved in together just three months later.

Why the Speculation Continues

The rocky start earned the couple significant public criticism, which fans think is part of why they’ve kept a low profile since, largely avoiding PDA and joint appearances throughout the “Wicked” press tours despite being together for several years now. That low visibility hasn’t slowed the relationship down privately, according to fans following it closely, which is why speculation continues that an engagement could still be announced quietly before 2027.

Bradley Cooper and Gigi Hadid

The Rumor That Started It All

According to a source who spoke to the Daily Mail, Cooper reportedly asked Gigi’s mother, Yolanda Hadid, for permission to propose, telling her he wanted her to know how serious he was about building a life with Gigi in New York.

What Fans Are Reading Into It

The reported conversation with Yolanda is being treated by fans as one of the clearest engagement signals of any couple on this list, with some predicting a holiday-season proposal timed around Christmas or New Year’s Eve. Cooper and Hadid have generally kept their relationship more private than some other A-list pairings, so any confirmation would likely come as a soft launch rather than a formal announcement.

Soft-Launch Signals By Couple

Engagement Odds at a Glance

What Fans Are Basing Their Predictions On

• Soft-launch photos: A hand, a set of keys, a matching outfit, often read as more telling than an official statement.
• Family involvement: Reports of a partner asking a parent for their blessing, as with Cooper and Yolanda Hadid, tend to move a couple straight to the top of prediction lists.
• Red carpet debuts: The first joint public appearance is treated as a major milestone, especially for couples who’d previously kept things private.
• Prediction markets and betting odds: Sites like Kalshi Culture have started assigning literal percentage odds to celebrity relationship milestones, turning fan speculation into something closer to a leaderboard.
• Timing around major events: Awards season, holidays, and premieres are the moments fans watch most closely for a possible ring reveal.

Which Couple Is Most Likely to Go First?

If fan chatter and prediction-market odds are anything to go by, Klay Thompson and Megan Thee Stallion currently sit at the top of the list, largely because their relationship has moved the fastest in public view and already carries a specific percentage attached to it. Bradley Cooper and Gigi Hadid aren’t far behind, since a reported conversation with a parent is usually read as one of the strongest signals a proposal is already in motion. Kylie Jenner and Timothée Chalamet look more like a 2026 story than an imminent one, given how deliberately slow their rollout has been so far. Ariana Grande and Ethan Slater remain the hardest to call, since their relationship has stayed largely out of view, meaning any engagement news could arrive with little warning at all.

Conclusion

None of these four couples have confirmed an engagement yet, and celebrity relationship speculation should always be read as exactly that, speculation. But between prediction market odds, family blessing rumors, and a steady stream of soft-launch photos, fans clearly think at least one of these pairings is close. If the pattern from 2025’s wave of engagements (Zendaya, Taylor Swift, Dua Lipa, Miley Cyrus) is any indication, the next round of celebrity engagement news is likely to arrive the same way theirs did: a ring spotted before any official statement.

FAQs

1. Is getting engaged at 23 too early?

There’s no perfect age to get engaged. What matters most is emotional maturity, shared goals, and a strong foundation rather than age alone.

2. What celebrities are newly engaged?

Recent celebrity engagements include stars like Taylor Swift, Zendaya, Dua Lipa, and Miley Cyrus. New engagement announcements continue to make headlines throughout 2026.

3. Which celebrity couple is rumoured to have had a secret wedding?

Several celebrity couples have faced secret wedding rumors, including Kylie Jenner and Timothée Chalamet. However, none of these reports have been officially confirmed.

4. What is the shortest engagement ever?

Some celebrity engagements have lasted only a few weeks before marriage. One of the shortest was Britney Spears and Kevin Federline, who married after a brief engagement.

5. Which celebrities got married recently?

Recent celebrity weddings include Taylor Swift and Travis Kelce, Zendaya and Tom Holland, Dua Lipa and Callum Turner, and Miley Cyrus and Maxx Morando.

6. Which celebrity married a normal person?

Several celebrities have married people outside the entertainment industry. Examples include Matt Damon, Eddie Redmayne, and Jerry Seinfeld, whose spouses are not Hollywood stars.

7. Which celebrity got married the most?

Zsa Zsa Gabor is widely known for having the most celebrity marriages, marrying nine times. Her personal life remains one of Hollywood’s most talked-about stories.

8. Who got married in secret?

Many celebrities have chosen private weddings, including Beyoncé and Jay-Z, Blake Lively and Ryan Reynolds, and Jennifer Aniston and Justin Theroux, who kept their ceremonies largely secret.

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