Ryan Reynolds Reveals Hilarious Truth About Pursuing Blake Lively—And It’s Not What You Expect

Ryan Reynolds and Blake Lively’s relationship is often seen as a playful and witty partnership, with the couple known for their lighthearted trolling dynamic and shared sense of humor. However, in a revealing moment during the 2021 SmartLess podcast, Reynolds offered a surprising and candid confession about how he pursued Lively early in their relationship—one that defied the usual Hollywood romance narrative.

A Friendship Before Romance

Reynolds and Lively first crossed paths on the set of Green Lantern in 2010, but their romantic relationship didn’t begin until 2011 after both had become single. They married in September 2012 and now share four children together: James, Inez, Betty, and Olin. Their relationship began with a period of friendship, which included a memorable double date with their respective partners. This early phase of platonic camaraderie laid the groundwork for what would eventually become a romance. As Reynolds shared on the SmartLess podcast in 2021, their relationship took time to evolve—something that sets the stage for his later, more surprising confession.

The Confession: Humorous and Vulnerable

In the July 2021 SmartLess podcast episode, Reynolds took a humorous and self-deprecating dive into his early pursuit of Lively. He reminisced about their time working together on Green Lantern, describing it as “the darkest crease in the anus of the universe,” before jokingly revealing the awkwardness of their connection at the time: “We were friends and buddies, and about a year and a half later we went on a double date but we were dating separate people.”

The confession escalated when Reynolds recounted a pivotal moment: “Next thing you know, she was going to Boston, I was going to Boston and I said, ‘Well, I’ll ride with you.’ We got on the train and we rode together. I was just begging her to sleep with me.” The humorous, somewhat risqué admission was then followed by an even more surprising detail: “A week later, I said, ‘We should buy a house together.'” This blend of vulnerability and humor, especially coming from a Hollywood heartthrob like Reynolds, was unexpected and caught many off guard, adding a more personal layer to his public persona.

Why the Confession Is Surprising

The surprise factor in Reynolds’ confession lies in several aspects. First, as a well-known actor with undeniable charm, one might assume Reynolds wouldn’t need to “beg” for romantic attention, making his candidness about the situation both relatable and humorous. It also subverts typical expectations of a glamorous Hollywood courtship, emphasizing a more awkward and genuine side of their relationship.

The context also adds a charming, almost fairytale-like quality to the story. The spontaneous train ride and Reynolds’ boldness in asking to buy a house together after just a week highlight the rapid progression of their connection, something that many can relate to despite the unique circumstances. This sense of unexpected but genuine attraction speaks to the more human side of celebrity relationships, offering fans a glimpse into the early days of one of Hollywood’s most adored couples.

The Confession’s Long-Lasting Impact

Reynolds’ 2021 admission remains one of the most surprising and relatable moments in his relationship with Lively. While the couple’s dynamic is typically defined by witty public exchanges and mutual teasing, this particular revelation stands out for its mix of vulnerability and humor. As of March 2025, this confession continues to be one of the most discussed aspects of their early romance, despite the couple’s recent shift in media attention due to other controversies, such as legal battles involving Lively’s allegations of sexual harassment on the set of It Ends With Us.

Though no similar confessions have been made in recent interviews or posts, Reynolds’ openness in sharing this moment in 2021 helped reinforce his reputation as a relatable and self-deprecating figure in the public eye.

Public Perception and Context

While Reynolds’ vulnerability during the SmartLess podcast was widely praised, especially for its humor, the changing media landscape around the couple may alter how some view this confession today. Given the ongoing controversies surrounding Lively, discussions about their relationship may take on a more critical tone in light of recent events. Yet, this confession remains a lighthearted and memorable anecdote in their shared narrative, often revisited in the context of their early days as a couple.

A Memorable Moment in Hollywood Romance

Ultimately, Reynolds’ confession about his pursuit of Blake Lively is a standout moment in their relationship—a rare glimpse into the more vulnerable and humorous aspects of their romance. While their marriage and family life have often been celebrated for their playful banter, this candid, surprising moment from their early relationship stands out as an example of how love can blossom in unexpected, and often awkward, ways. For fans of the couple, this confession remains one of the most relatable and memorable moments in their Hollywood romance.