Why Blake Lively and Penn Badgley’s relationship was always doomed: The red flag no one talked about

Why was Blake Lively and Penn Badgley never endgame?

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He was TV’s moody outsider, and she was the dazzling queen bee, but somehow, Penn Badgley and Blake Lively managed to turn their on-screen chemistry into a real-life romance. While filming Gossip Girl, their characters, Dan and Serena, had a rollercoaster love story, and off-screen, so did they. Even though they didn’t end up together in real life, their relationship had a decent run. But according to Penn Badgley, it was never really meant to last. One big reason? He had a hard time figuring out where his character ended and where he began.

What did Penn Badgley say about his relationship with Blake Lively?

Penn Badgley opened up about all this on the Call Her Daddy podcast, getting real about what it was like to be in his first high-profile relationship. He shared that playing Dan Humphrey full-time really blurred the lines for him, both emotionally and mentally. When you’re acting on a long-running show like Gossip Girl, you’re living that role day in and day out. He felt like he constantly had to prove himself and perform, not just on camera, but in life. And because fans often saw him as “Dan” even off set, it made things even messier. “People would yell Dan’s name at me in the street, and I’d still have to be him at work every day. After a while, you kind of lose sight of who you are,” he said. Basically, being stuck in character made it nearly impossible for him to fully show up in his own relationship.

Is there any ongoing drama between Blake Lively and Penn Badgley?

But despite all the complications, there’s no drama between them now. Both Penn and Blake have moved on, he’s married to singer Domino Kirke, and she’s built her own fairytale with Ryan Reynolds. In fact, Penn gives Blake a lot of credit for keeping him grounded during a time he says could’ve easily gone off the rails. He once said that Blake was like a steady hand during those wild Gossip Girl years, keeping “Lonely Boy” from becoming truly lost.

Looking back, Penn also admitted that dating someone as wildly famous as Blake Lively came with its own unique challenges, like feeling invisible. In an interview with Variety, he mentioned that most of the attention back then was on Blake, not him. And honestly? He didn’t totally mind. He was dealing with some inner struggles and personal battles, and Blake helped him stay on the right path. “I never had issues with substances,” he shared. “Blake didn’t drink either, and in a way, our relationship helped me avoid going down some darker roads.”

After being together for about three years, the two eventually broke up. But because Gossip Girl wasn’t going anywhere, they still had to show up to work and play love interests. Somehow, they managed to keep things professional and drama-free, at least in front of the cameras. There was no visible awkwardness, just business as usual.

In the end, Penn reflected that Gossip Girl was both what brought them together and what quietly drove them apart. “We were deeply wrapped up in the show,” he told Elle. “It was six years of intense filming, and our relationship helped us get through that — but it was also shaped by that same pressure.” For him, it was a mix of good and bad — a meaningful relationship that taught him a lot, even if it wasn’t built to last forever.