Here's where you could potentially spot Theo James in Toronto this week

If you love Theo James as much as Theo James unabashedly loves Toronto's Dufferin Mall, you're in luck. You could potentially run into the actor elsewhere in the city this week.

Granted, the Golden Globe-nominated actor will be hard at work filming his new 1950s mafia movie with funnyman Vince Vaughn. But, if you wish to admire the smouldering, dark-haired heartthrob from afar, this is your chance.

Filming for The Bookie and the Bruiser has been well underway for a couple of weeks now, with fans having already spotted James in action along Church St. 

Theo James spotted on the set of The Bookie and The Bruiser in Toronto

🎥 aafiyasomani on TikTok pic.twitter.com/TGgCvNLfN5

— Theo James Updates (@LeftKidney4Theo) April 25, 2026

Beginning April 29 through May 1, production will take over both the interior and exterior of 519 Jarvis St., according to a filming notice. 

Filming Update#TheBookieAndTheBruiser, starring Theo James and Vince Vaughn, will be filming at 519 Jarvis St on April 29–30 and May 1, from 12 pm to 2 am. 👊🎥🎬 https://t.co/Pw0mVzuaEs pic.twitter.com/kKW8g1Oj50

— Toronto Filming (@TOFilming_EM) April 28, 2026

If you're well-versed in Toronto lore, you'll recognize this address as the iconic Chester D. Massey House, right next to the Keg Mansion in the Church Wellesley Village neighbourhood. The heritage site has sat abandoned for years and has long been linked to some pretty eerie hauntings.

With that kind of rich history baked into its walls, it's easy to see why it makes the perfect backdrop for a drama set in the 1950s.

James does seem like a gentleman who would indulge in a steak and scotch after a long shoot day, so how nice would it be if you got seated next to or close to him at The Keg?

But if you're not in this particular neck of the woods, you might still catch the actor between takes or in off-hours wandering through Ossington or Queen West, two neighbourhoods he recently described as "sexy." 

Production for James' movie is scheduled to wrap by the end of May, so you have plenty of time for starsighting.