From Kylie Jenner to Sydney Sweeney to Katy Perry: Here’s Which Star Is Most Likely to Get Engaged This Year
Love has been in the air for quite a few celebrities for a while now, and some are wondering if they’ll be getting engaged soon.
Taylor Swift and Travis Kelce had the biggest engagement announcement of 2025, so who will have the biggest engagement announcement of 2026? Could it be Sydney Sweeney and Scooter Braun, or Kylie Jenner and Timothée Chalamet, or KatyPerry and Justin Trudeau, or how about Harry Styles and Zoë Kravitz? Or maybe there’s an engagement over the next 10 months for new couple Kim Kardashian and Lewis Hamilton.
Now the entertainment experts at OLBG are sharing the latest predictions for which duo is most likely to get engaged this year.
Jake Ashton, Entertainment Betting Expert at OLBG.com, told Showbiz Cheat Sheet, “Celebrity engagement betting is driven by visibility and momentum. One interview, one red carpet appearance, or one Instagram post can move odds dramatically. Some big names feature in the market, and it’s the Hamilton/Kardashian coupling that has the most attention following their Super Bowl appearance together.”
While the SKIMS founder and F1 driver are generating the most buzz, they’re not the odds-on favorite couple to get engaged in 2026. Instead, the favorites are Sweeney and Braun, tied with Styles and Kravitz, both with an implied probability chance of 33.3%.
Kardashian and Hamilton have a 300 (25%) probability of getting engaged.
The reality star’s sister, Kylie Jenner, and her beau, Timothée Chalamet, are also priced at 300 with 25% probability of an engagement in 2026.
And just behind the Khy founder and the actor are Katy Perry and Justin Trudeau at 400 with a 20% probabilty. The former Canadian Prime Minister has been legally separated from his wife, Sophie Grégoire Trudeau, since 2023, while Perry and Orlando Bloom ended their relationship in June 2025.
