Dylan O’Brien favored to be Taylor Swift’s Next Boyfriend

  • Taylor Swift is reportedly back on the market after calling it off with longtime beau Joe Alwyn
  • Dylan O’Brien (+400) and Shawn Mendes (+500) are close friends with the pop star  
  • Harry Styles (+500), John Mayer (+1000) and Jake Gyllenhaal (+1600) are just a few of the exes on the board

With the news that Taylor Swift has broken it off with longtime boyfriend Joe Alwyn after six years, it’s only natural to look at who the 33-year-old singer-songwriter might date next. Actors, musicians, pro athletes, tech billionaires, and two actual princes are all listed among the pop star’s possible matches.

Before we look at the list of celebrity suitors, here’s where you can check out the top betting sites for Entertainment in 2023 and the latest betting odds for the 2024 Oscars.

Taylor Swift Next Boyfriend

Dylan O'Brien+400
Harry Styles+500
Shawn Mendes+500
Pete Davidson+800
John Mayer+1000
Jake Gyllenhaal+1600
Jack Dorsey+2000
Michael B. Jordan+2000
Milo Ventimiglia+2200
Bradley Cooper+2500
Connor Kennedy+2500
Luka Doncic+2500
Pedro Pascal+2500
Scott Eastwood+2500
Tom Brady+2500
Alexander Skarsgard+3000
Andrew Garfield+3000
Austin Butler+3000
Devin Booker+3000

Dylan O’Brien tops the list

Who is Dylan O’Brien (+400), you ask? Swift once told Jimmy Fallon, “Dylan and I have become really close friends” and the 31-year-old Teen Wolf star was spotted outside her New York City apartment in early April. O’Brien also appeared in All Too Well, a 2021 short film that was written and directed by T.Swizzle herself.

Shawn Mendes (+500) has collaborated with Swift in the past and the two apparently have a longtime friendship. However, recent tabloids have linked the Canadian pop star with Camila Cabello. Taylor has also been pals with Drake (+1800) for years, aside from a possible social media spat in 2022.

Long list of exes

Oddsmakers always feature exes prominently when posting celebrity dating odds because, even if the people now hate each other, there’s at least definitive proof they once slept together. While some former lovers such as Calvin Harris, Tom Hiddleston and Taylor Lautner are not listed, there are plenty on the board.

Harry Styles (+500) dated Swift for three months almost a decade ago. Tay Tay bedded John Mayer (+1000) and Jake Gyllenhaal (+1600) way back in 2010. She also enjoyed a summer 2012 fling with Robert Kennedy’s grandson, Connor Kennedy (+2500), and was spotted with Alexander Skarsgard (+3000) in 2013.

Dylan O'BrienTaylor Swift's Next Boyfriend
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Shawn MendesTaylor Swift's Next Boyfriend
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All eyes on Pete Davidson

Whenever a notable female celebrity breaks it off with her partner, Pete Davidson (+800) inevitably trends on Twitter. Gisele Bündchen, Melania Trump, and Taylor Swift being the most recent examples. The SNL alum leads a curious list of names that likely have no connection whatsoever to the songstress.

Twitter founder Jack Dorsey (+2000) and Twitter destructor Elon Musk (+6000), for instance. There are popular actors such as Creed star Michael B. Jordan (+2000), Pedro Pascal (+2500)Brad Pitt (+3500) and Leonardo DiCaprio (+4000). And don’t forget athletes like Luka Doncic (+2500), Devin Booker (+3000) and Tom Brady (+2500). There are even two royal family members: Prince Sébastien of Luxembourg (+3000) and Prince Wenzel of Liechtenstein (+4000). 

Best Bet

Fernando Alonso is not even on the board despite rumors connecting the Spanish Formula 1 driver with Swift. For that reason, you should proceed with caution and only make a fun wager with low stakes.

For my money, the silliest, most-implausible name you can bet on is Shohei Ohtani (+6000). This would be yet another impossible milestone achievement for the two-way Japanese baseball superstar.

Shohei OhtaniTaylor Swift's Next Boyfriend
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Steve Starr

Steve is the quintessential American sports enthusiast. He has mastered the art of Sundays, devoting them to football, and barbecue parties. He proudly wears the hats of a good father, husband and a great dog owner. Aside from his decades of contributing to different top-tier sports publications, Steve has also found his niche on Twitter, where he publishes funny and relatable sports-related insights. When he's not busy tweeting, Steve loves to watch each game unfold live. He possesses an innate talent for finding humor in the sports world, appreciating both the thrilling moments and the comedic mishaps that make each event unique.