5 Shocking Details About Blake Lively And Ben Affleck's 'Awkward' Collaboration On The Town

The enduring connection between Blake Lively and Ben Affleck is a fascinating piece of Hollywood history, rooted almost entirely in a single, intense collaboration over a decade ago: the critically acclaimed 2010 crime thriller, The Town. While there is no new professional or romantic news regarding the two stars in late 2024 or 2025—both are currently focused on separate, high-profile projects and personal lives—the mystique surrounding their time on Ben Affleck's Boston-set film continues to captivate fans and fuel online speculation.

This article dives deep into the true story of their work together, from the surprising casting that landed the Gossip Girl star in a gritty dramatic role, to the on-set moments and infamous scene that both actors have publicly described as "awkward," revealing how their brief professional intersection shaped their careers and solidified their place in Hollywood lore. We'll explore the rumors, the professional praise, and the lasting advice that remains their strongest bond.

Blake Lively and Ben Affleck: A Dual Hollywood Biography

To understand the context of their collaboration, it is essential to look at where both stars were in their careers when they met on the set of The Town in 2010, and where they stand today in 2025.

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Blake Lively: Profile and Biography

• Full Name: Blake Ellender Brown (Professionally known as Blake Lively)
• Date of Birth: August 25, 1987
• Place of Birth: Los Angeles, California, U.S.
• Spouse: Ryan Reynolds (m. 2012)
• Notable Roles: Serena van der Woodsen in Gossip Girl, Bridget Vreeland in The Sisterhood of the Traveling Pants, Adaline Bowman in The Age of Adaline, Emily Nelson in A Simple Favor, and Lily Bloom in the upcoming 2024 film It Ends with Us.
• Current Status (2024/2025): High-profile actress, entrepreneur (Betty Buzz founder), and mother of four. She recently settled a legal matter regarding her contract for the 2024 film It Ends with Us.

Ben Affleck: Profile and Biography

• Full Name: Benjamin Géza Affleck-Boldt
• Date of Birth: August 15, 1972
• Place of Birth: Berkeley, California, U.S.
• Spouse: Jennifer Lopez (m. 2022; divorced 2025), Jennifer Garner (m. 2005; div. 2018)
• Notable Works: Starred in Good Will Hunting (Academy Award for Best Original Screenplay), directed and starred in Argo (Academy Award for Best Picture), Gone Girl, Batman v Superman: Dawn of Justice, and directed The Town.
• Current Status (2024/2025): A-list actor, director, and producer. His personal life, particularly his recent divorce from Jennifer Lopez in early 2025, has been a major media focus.

The Town: The True Story Behind the Rumors

The 2010 film The Town, directed by and starring Ben Affleck, is the sole professional link between the two stars. The movie, based on Chuck Hogan's novel Prince of Thieves, is a gritty crime drama set in Boston, where Affleck's character, Doug MacRay, falls for a bank manager (Rebecca Hall) while simultaneously grappling with his life as a career criminal. Blake Lively was cast in a pivotal, darker role as Krista Coughlin, the sister of a volatile associate (Jeremy Renner) and the mother of Doug’s child—a role starkly different from her glamorous persona on Gossip Girl.

1. The Casting Choice That Shocked Hollywood

Ben Affleck took a major risk by casting Blake Lively. At the time, she was primarily known for her role as the wealthy, stylish Serena van der Woodsen on the CW's hit show Gossip Girl. Affleck, however, saw her potential for a raw, dramatic performance. He praised her eagerness, noting that she was "terrific" and committed to doing research, including spending time in the Boston neighborhood of Charlestown to authentically portray the struggling, drug-addicted single mother, Krista Coughlin. This role was a crucial turning point, proving Lively’s dramatic range beyond her teen-drama fame.

2. Blake Lively’s 'Awkward' First Day on Set

One of the most talked-about aspects of their collaboration was the filming of an intimate scene between their characters. Blake Lively later revealed that the sex scene with Affleck was "really awkward," primarily because it was scheduled for her very first day of shooting. She was thrown into one of the most vulnerable and intense scenes of the film immediately, a challenging start for any actor.

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Affleck, who was serving as both director and co-star, had a different perspective on the timing. He reportedly chose to shoot the scene early to "break the ice," believing it was better to get the difficult, intimate moments out of the way first. Lively, then only 23, was tasked with portraying a character far removed from her real life, making the experience even more challenging.

The Lasting Impact and Surprising Anecdotes

Beyond the film's success and the inevitable on-set rumors that follow two attractive, single co-stars, the professional relationship between Lively and Affleck left a lasting mark on both their careers.

3. The Best Acting Advice She Ever Received

Despite the initial awkwardness, Lively has credited Ben Affleck with providing her with some of the best professional advice of her career. The key takeaway was about the importance of being present and authentic in her performance. Lively recalled Affleck telling her to pay attention to what was genuinely "working and what is not," urging her to "stay alive" and constantly adapt to the moment. This advice helped her transition from a structured television role to the spontaneity required for a major motion picture.

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4. The Hilarious Matt Damon Revelation

A lighter, yet highly revealing, anecdote from the set involves Affleck's long-time friendship with Matt Damon. Ben Affleck recalled taking Blake Lively around the Boston area for research. When he pointed out Matt Damon's house, Lively, who was still relatively new to the A-list Hollywood inner circle, was reportedly shocked. She had no idea that Affleck and Damon, two of the industry's biggest stars, were genuine friends, a moment Affleck found quite amusing and indicative of their different industry backgrounds at the time.

5. The Current Connection: A Shared High-Profile Life

While they are not currently working together, the two stars share a unique position in Hollywood as halves of two of the most scrutinized celebrity marriages of the 21st century. Blake Lively is famously married to actor Ryan Reynolds, forming one of the industry's most beloved and stable power couples. Ben Affleck, after his high-profile marriage and subsequent divorce from Jennifer Garner, reignited the 'Bennifer' phenomenon with Jennifer Lopez before their divorce in 2025. This shared experience of intense media scrutiny over their personal lives—a world away from the gritty drama of The Town—serves as a quiet, modern connection between the two.

Conclusion: The Legacy of a Brief but Intense Collaboration

The story of Blake Lively and Ben Affleck is not one of a secret romance or an ongoing partnership, but rather a powerful example of a brief, intense professional collaboration that yielded a critically acclaimed performance and provided one star with career-defining advice. Lively’s role as Krista Coughlin remains one of her most complex and lauded dramatic turns, a testament to Ben Affleck’s eye for casting and his ability to push actors out of their comfort zone. The "awkward" sex scene and the on-set rumors are merely footnotes to the lasting legacy of The Town, a film that proved Blake Lively was far more than just a Gossip Girl and solidified Ben Affleck's reputation as an accomplished director.

Today, as both stars navigate the complexities of their separate, high-profile lives—Lively with her family and business ventures, and Affleck with his directorial projects and personal changes in 2025—their 2010 collaboration remains the definitive, and most intriguing, chapter in their shared history.