When did Penn Badgley and Blake Lively date? Gossip Girl star explains why dating his former co-star was "the struggle" 

From L to R, Penn Badgley, Blake Lively: source- Getty Images
From L to R, Penn Badgley, Blake Lively: source- Getty Images

Gossip Girl alum Penn Badgley offered a candid look into his early 20s, relationships, and the “struggles” of navigating fame while dating Blake Lively in a recent episode of the Call Her Daddy podcast, aired on April 23, 2025.

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Speaking with host Alex Cooper, Badgley reflected on his time living in New York and how he balanced his personal life with his professional obligations.

During the interview, Cooper asked whether, during his relationship with Gossip Girl co-star Blake Lively, he could “separate” his personal life from his work, or if the two felt “merged,” Penn Badgley admitted the lines were often blurred.

"That’s a great question because it was the struggle", Penn Badgley said.
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According to People magazine, Penn Badgley and Blake Lively dated from 2007 to 2010, just like their characters on Gossip Girl, which ran from 2007 to 2012. The New York Post says they remained friendly co-stars after their breakup

During the aforementioned interview, the actor added that the show’s popularity, combined with his rising fame, post his relationship with Blake Lively, made things even more complex.

"When you do a television show, you’re doing it constantly.. Because of the nature of that show and the celebrity culture at the time, I was frequently asked about dating advice in interviews", Badgley added
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As his fame rose, Badgley noted that fans and media began to conflate him with his character, Dan Humphrey.

“What starts to happen when you’re in this one role for a long time — the aspect of celebrity being a part of it, a huge part of it — there is not enough separation, I think, for anybody. You’re seen as this person, you’re called their name out on the street. You also constantly have to be that person at work” he explained.
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Badgley admitted that in his early 20s, he lacked "emotional maturity to understand how to differentiate" himself from his role, particularly “in terms of self-worth.

So he naturally believed that what "people seemed to think of Dan" the character, was the same as what "people thought" of Penn Badgley himself.


Penn Badgley opens up about past relationships, before dating Blake Lively on Call Her Daddy podcast

Penn Badgley at the Netflix's "You" Season 5 New York Screening - Source: Getty
Penn Badgley at the Netflix's "You" Season 5 New York Screening - Source: Getty

During his candid conversation on the Call Her Daddy podcast, You actor Penn Badgley reflected on his romantic journey, shedding light on his early relationship before dating Blake Lively. Opening up about his younger years, Badgley admitted that the idea of casual dating never quite resonated with him.

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"I think I’ve been on one date in my life...I remember just the feeling of not knowing. You feel like you’re constantly — even though no one may be actually asking you to do this — you feel like you’re constantly needing to prove yourself in some manner. Otherwise, what are you doing?", he said.
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Before dating Blake Lively in his 20s, the Easy A actor noted that he only had a "had a handful of long relationships", but he "really did not date". He also described dating as "a bit of a performance", sharing how he always sought deeper emotional bonds.

"I really longed for that kind of connection, that kind of intimacy", he added.

He also shared a particularly formative experience from his teen years:

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"I also had a very long and difficult relationship in my teen years...That marked me, and I actually remember thinking when I got out of it at 19, I was just like, 'That was a way to start it all. I wonder what effects it’s gonna have on me,’ you know?'"

As per US Magazine, Feb 28, 2025, Badgley had three long-term relationships in his 20s- one with Blake Lively, then with Zoë Kravitz, from 2011 to 2013, followed by Domino Kirke, whom he married in 2017.

At present, both the Gossip Girl alums are busy with the promotional run of their latest releases. Blake Lively's Another Simple Favour is scheduled for global release on Amazon Prime on May 1, 2025 and Penn Badgley's You returns to Netflix for its fifth and final season on Thursday, April 24.

Edited by Divya Singh
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