30 Hollywood Celebrities You’d Be Surprised to Know Have Dated Each Other in the Past

You know how Hollywood seems like a pretty small world sometimes? Well, get ready to be surprised, because the entertainment industry’s dating scene is even more interconnected than you might think. While we all remember the headline-grabbing couples like Brangelina or Tom and Nicole, there’s a whole treasure trove of fascinating relationships that time has almost forgotten.
Brad Pitt and Angelina Jolie in Mr. & Mrs. Smith (2005) | Credits: 20th Century Studios, Summit Entertainment, Fox Atomic
What makes these forgotten couples so fascinating isn’t just the “wait, they dated?” factor – it’s how these relationships often challenge everything we think we know about celebrity pairings.
Ready to dive into some of Hollywood’s most surprising romantic connections? Let’s start with a couple that might really throw you for a loop.
1. Sandra Bullock and Ryan Gosling Sandra Bullock and Ryan Gosling in Murder by Numbers (2002) | Credits: Warner Bros. Pictures...
Brad Pitt and Angelina Jolie in Mr. & Mrs. Smith (2005) | Credits: 20th Century Studios, Summit Entertainment, Fox Atomic
What makes these forgotten couples so fascinating isn’t just the “wait, they dated?” factor – it’s how these relationships often challenge everything we think we know about celebrity pairings.
Ready to dive into some of Hollywood’s most surprising romantic connections? Let’s start with a couple that might really throw you for a loop.
1. Sandra Bullock and Ryan Gosling Sandra Bullock and Ryan Gosling in Murder by Numbers (2002) | Credits: Warner Bros. Pictures...
- 1/7/2025
- by Sweta Rath
- FandomWire
Similar News
Mikey Madison And Kirsten Dunst To Star In Alejandro Landes Echavarría’s ‘Reptilia’ From Imperative, Pastel, Black Bear And Af Films
- 5/9/2025
- by Justin Kroll
- Deadline Film + TV

Netflix’s Christian Nationalism Doc ‘Apocalypse in the Tropics’ Set for Summer Release, Fall Awards Push (Exclusive)
- 5/9/2025
- by Scott Feinberg
- The Hollywood Reporter - Movie News

Jane Schoenbrun aims to make a sleepover classic with Teenage Sex and Death at Camp Miasma, starring Gillian Anderson
- 5/9/2025
- by Cody Hamman
- JoBlo.com

Hot Cannes Titles, Summer Movies, and Hollywood’s Tariff Threat — This Week’s ‘Screen Talk’ Podcast
- 5/9/2025
- by Anne Thompson and Ryan Lattanzio
- Indiewire
Ben Stiller's $128M Dark Comedy Lands On Netflix's Global Charts 18 Years Later
- 5/9/2025
- by Adam Bentz
- ScreenRant

Alan Ritchson Splits With Longtime Manager Dan Spilo (Exclusive)
- 5/8/2025
- by Aaron Couch
- The Hollywood Reporter - Movie News

IMDb.com, Inc. takes no responsibility for the content or accuracy of the above news articles, Tweets, or blog posts. This content is published for the entertainment of our users only. The news articles, Tweets, and blog posts do not represent IMDb's opinions nor can we guarantee that the reporting therein is completely factual. Please visit the source responsible for the item in question to report any concerns you may have regarding content or accuracy.